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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Pages o1098-o1099
https://doi.org/10.1107/S1600536810013620

4-Acetamido-N-(λ5-tri­phenyl­phospho­ranyl­­idene)benzene­sulfonamide

Biserka Prugovečki,a* Marina Marinković,b Mladen Vinkovićb‡ and Miljenko Dumićc

aLaboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia, bPLIVA Croatia Ltd, TAPI Research and Development, Prilaz baruna Filipovića 29, HR-10000 Zagreb, Croatia, and cDepartment of Biotechnology, University of Rijeka, S. Krautzeka bb, HR-51000 Rijeka, Croatia
*Correspondence e-mail: biserka@chem.pmf.hr

(Received 8 March 2010; accepted 13 April 2010; online 17 April 2010)

There are two independent mol­ecules per asymmetric unit of the title compound, C26H23N2O3PS. Their superposition shows that they differ in the conformation of the CH3CO– group and the benzene rings from the triphenyl­phospho­rane group. In the crystal structure, independent mol­ecules are inter­conected by strong N—H⋯O hydrogen bonds, forming infinite chains along the a axis.

Related literature

For related structures, see: Andersen et al. (1999[Andersen, N. G., Ramsden, P. D., Che, D., Parvez, M. & Keay, B. A. (1999). Org. Lett. 1, 2009-2011.], 2001[Andersen, N. G., Ramsden, P. D., Che, D., Parvez, M. & Keay, B. A. (2001). J. Org. Chem. 66, 7478-7486.], 2004[Andersen, N. G., Parvez, M., McDonald, R. & Keay, B. A. (2004). Can. J. Chem. 82, 145-7161.]); Matano et al. (2002[Matano, Y., Nomura, H. & Suzuki, H. (2002). Inorg. Chem. 41, 1940-1948.]); Monkowius et al. (2004[Monkowius, U. V., Nogai, S. & Schmidbaur, H. (2004). Dalton Trans. pp. 1610-1617.]); Zhu et al. (1997[Zhu, S., Xu, B., Qin, C. & Xu, G. (1997). Inorg. Chem. 36, 4909-4911.]). For the synthesis, see: Ashley et al. (1947[Ashley, J. N., Buchanan, G. L. & Easson, A. P. T. (1947). J. Chem. Soc. pp. 60-67.]); Khmel'nitzkaya & Mikhel's (1934[Khmel'nitzkaya, I. & Mikhel's, V. (1934). Zh. Obshch. Khim. pp. 452-455.]). For structural and synthetic studies of azirine anti­hyperglycaemics, see; Dumić et al. (1993[Dumić, M., Filić, D., Vinković, M., Jamnicky, B. & Kamenar, B. (1993). Tetrahedron Lett. 34, 3639-3642.], 1995[Dumić, M., Vinković, M., Filić, D., Jamnicky, B., Eškinja, M. & Kamenar, B. (1995). J. Med. Chem. 38, 3034-3042.]); Filić et al. (1996[Filić, D., Vinković, M., Jamnicky, B. & Dumić, M. (1996). Croat. Chem. Acta, 69, 631-641.]); Orešić et al. (2001[Orešić, M., Filić, D., Prugovečki, B., Vinković, M. & Dumić, M. (2001). Croat. Chem. Acta, 74, 667-682.]); Prugovečki et al. (2005[Prugovečki, B., Marinković, M., Vinković, M. & Dumić, M. (2005). Acta Cryst. E61, o2844-o2846.], 2006[Prugovečki, B., Marinković, M., Vinković, M. & Dumić, M. (2006). Croat. Chem. Acta, 79, 219-226.]); Vinković et al. (1993[Vinković, M., Dumić, M. & Kamenar, B. (1993). Acta Cryst. C49, 1661-1663.]); Žegarac et al. (2010[Žegarac, M., Marinković, M., Prugovečki, B., Vinković, M. & Dumić, M. (2010). In preparation.]).

[Scheme 1]

Experimental

Crystal data

  • C26H23N2O3PS

  • Mr = 474.49

  • Monoclinic, P 21 /n

  • a = 15.0419 (10) Å

  • b = 18.6355 (10) Å

  • c = 18.5917 (18) Å

  • β = 113.413 (10)°

  • V = 4782.4 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 295 K

  • 0.56 × 0.30 × 0.15 mm
Data collection

  • Oxford Diffraction Xcalibur CCD diffractometer

  • 32329 measured reflections

  • 8441 independent reflections

  • 6309 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.106

  • S = 1.04

  • 8441 reflections

  • 595 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O2′i 0.86 2.11 2.966 (2) 173
N2′—H2′⋯O2ii 0.86 2.11 2.961 (2) 174
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013620/bg2337sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013620/bg2337Isup2.hkl

checkCIF report


Comment top

As a part of our ongoing research on the synthetic and structural studies of 1-sulfonyl-1a,2,6,6a-tetrahydro-1H,4H-[1,3]dioxepino[5,6-b]azirine antihyperglycaemics (Dumić et al. 1993 ; 1995, Filić et al. 1996, Vinković et al. 1993, Orešić et al. 2001 and Prugovečki et al.2005 ; 2006), we required suitable synthons carrying 4-acetylaminobenzenesulfanyl and 4-acetylaminobenzenesulfonyl pattern. Thus, the 4-acetylaminobenzenesulfonyimino-triphenylphosphorane (Title compound, I) and bis(4-acetylaminophenyl) disulfide compound (II) were chosen for this study. We prepared both of them in the same reaction, i.e. by treatment of 4-acetylaminobenzenesulfonylazide with triphenylphosphine in acetonitrile at room temperature (Scheme 1). 4-Acetylaminobenzenesulfonyimino-triphenylphosphorane (Title compound, I) was obtained as colorless prisms (m.p. 495-497 K). Bis(4-acetylaminophenyl) disulfide (compound II) was obtained as a yellow solid (m.p. 485-488 K), i.e. in one of its three known forms; m.ps. 488 K, 454-455 K and 395 K respectively (Khmel'nitzkaya, et al. 1934). Its structure and solid state behaviour will be published elsewhere (Žegarac et al. 2010).

In the title compound, C26H23N2O3PS,(I), there are two independent molecules per asymmetric unit. Their superposition shows that they are different in the conformation of the CH3CO group and the benzene rings from the triphenylphosphorane group. In the crystal structure independent molecules are interconected by strong N—H···O hydrogen bonds forming infinite one-dimensional chains along the a axis.

Related literature top

For related structures, see: Andersen et al. (1999, 2001, 2004); Matano et al. (2002); Monkowius et al. (2004); Zhu et al. (1997). For the synthesis, see: Ashley et al. (1947); Khmel'nitzkaya & Mikhel's (1934). For structural and synthetic studies of azirine antihyperglycaemics, see; Dumić et al. (1993, 1995); Filić et al. (1996); Orešić et al. (2001); Prugovečki et al. (2005, 2006); Vinković et al. (1993); Žegarac et al. (2010).

Experimental top

Triphenylphosphine (28.18 g, 0.107 mol) was added in small portions to a stirred solution of 4-acetylaminobenzenesulfonyl azide (13.0 g, 50.4 mmol) [prepared according Ashley et al. (1947)] in acetonitrile (211 ml) at 273 K. After being stirred for 3 hrs at room temperature, the mixture was concentrated under reduced pressure to dryness. The residue was purified by silicagel column chromatography (dichloromethane-methanol-25 % ammonia, 10:1:0.3 v/v) to afford the title compound (I) as a colorless solid [5.9 g, 22.7 %; m.p. 491-495 K; Rf = 0.32 (dichloromethane-methanol- 25 % ammonia, 10:1:0.3 v/v)]. Single crystals suitable for X-ray diffraction were prepared by recrystallization from ethyl acetate-methanol , 1:1 v/v). M.p. 495-497 K. Spectroscopic analysis: IR (KBr) νmax/cm-1: 3305, 3269, 3190, 3116, 3057, 1691, 1594, 1536, 1485, 1437, 1400, 1372, 1315, 1252, 1194, 1170, 1131, 1085, 1031, 1015, 998, 954, 851, 801, 790, 753, 723, 692, 638, 620. 1H NMR (DMSO-d6) δ/ppm: 10.12 (s, 1H, NH), 7.52 i 7.40 (d.d., 4H, J=4.3, H-arom.), 7.73-7.68 and 7.59-7.57 (2 m, 15H, H-arom.), 2.06 (s, 3H, CH3). 13C NMR (DMSO-d6) δ/ppm: 141.10 (s), 140.32 (s), 125.93 (d), 117.96 (d) (C arom.), 133.05 (d), 132.60 (d), 128.90 (d), 126.94 (d, J(C—P)=102.9) (C-arom), 24.04 (q, CH3).

Evaporation of other selected fractions to dryness afford bis(4-acetylaminophenyl) disulfide (II) as a TLC pure yellow solid [5.7 g, 31.5 % m.p. 485-488 K; Rf = 0.26 (dichloromethane-methanol-25 % ammonia, 10:1:0.3 v/v)]. Spectroscopic analysis: IR (KBr) νmax/cm-1: 3291, 3246, 3178, 3105, 3058, 1681, 1658, 1608, 1593, 1538, 1490, 1397, 1367, 1317, 1292, 1263, 1175, 1121, 1014, 967, 838, 825, 816, 758, 703, 604. 1H NMR (DMSO-d6) δ/ppm: 10.71 (s, 2H, NH), 7.59 and 7.42 (dd, 8H, H arom, J=8.7), 2.04 (s, 6H, CH3). 13C NMR (DMSO-d6) δ/ppm: 168.50 (s, CO), 139.50 (s), 130.10 (d), 129.10 (s), 119.50 (d) (C arom), 24.20 (q, CH3).

Refinement top

H atoms were positioned geometrically, C-H: 0.93-0.96Å, N-H: 0.86Å, and allowed to ride, with U(H)=1.2/1.5× Ueq(host). In order to avoid beamstop shadowing effects theta(min) was set to 3.24°, with what 20 reflections below this value were left aside the data set.

Structure description top

As a part of our ongoing research on the synthetic and structural studies of 1-sulfonyl-1a,2,6,6a-tetrahydro-1H,4H-[1,3]dioxepino[5,6-b]azirine antihyperglycaemics (Dumić et al. 1993 ; 1995, Filić et al. 1996, Vinković et al. 1993, Orešić et al. 2001 and Prugovečki et al.2005 ; 2006), we required suitable synthons carrying 4-acetylaminobenzenesulfanyl and 4-acetylaminobenzenesulfonyl pattern. Thus, the 4-acetylaminobenzenesulfonyimino-triphenylphosphorane (Title compound, I) and bis(4-acetylaminophenyl) disulfide compound (II) were chosen for this study. We prepared both of them in the same reaction, i.e. by treatment of 4-acetylaminobenzenesulfonylazide with triphenylphosphine in acetonitrile at room temperature (Scheme 1). 4-Acetylaminobenzenesulfonyimino-triphenylphosphorane (Title compound, I) was obtained as colorless prisms (m.p. 495-497 K). Bis(4-acetylaminophenyl) disulfide (compound II) was obtained as a yellow solid (m.p. 485-488 K), i.e. in one of its three known forms; m.ps. 488 K, 454-455 K and 395 K respectively (Khmel'nitzkaya, et al. 1934). Its structure and solid state behaviour will be published elsewhere (Žegarac et al. 2010).

In the title compound, C26H23N2O3PS,(I), there are two independent molecules per asymmetric unit. Their superposition shows that they are different in the conformation of the CH3CO group and the benzene rings from the triphenylphosphorane group. In the crystal structure independent molecules are interconected by strong N—H···O hydrogen bonds forming infinite one-dimensional chains along the a axis.

For related structures, see: Andersen et al. (1999, 2001, 2004); Matano et al. (2002); Monkowius et al. (2004); Zhu et al. (1997). For the synthesis, see: Ashley et al. (1947); Khmel'nitzkaya & Mikhel's (1934). For structural and synthetic studies of azirine antihyperglycaemics, see; Dumić et al. (1993, 1995); Filić et al. (1996); Orešić et al. (2001); Prugovečki et al. (2005, 2006); Vinković et al. (1993); Žegarac et al. (2010).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecule I with the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Overlaped structures of independent molecules of compound I, showing structural differences.
[Figure 3] Fig. 3. Packing of the molecules in the unit cell. Hydrogen bonds (d(N2—H2···O2'(-x + 1/2, y - 1/2,-z+1/2)=2.966 (2) Å and N2'-H2'···O2(-x + 3/2, y + 1/2,-z+1/2)=2.961 (2) Å) are shown as dotted lines and hydrogen atoms that are not involved in hydrogen bonding are omitted for clarity.
[Figure 4] Fig. 4. Synthetic route to the molecule I.
4-Acetamido-N-(λ5-triphenylphosphoranylidene)benzenesulfonamide top
Crystal data top
C26H23N2O3PSF(000) = 1984
Mr = 474.49Dx = 1.318 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1548 reflections
a = 15.0419 (10) Åθ = 15–25°
b = 18.6355 (10) ŵ = 0.23 mm−1
c = 18.5917 (18) ÅT = 295 K
β = 113.413 (10)°Plate, colourless
V = 4782.4 (6) Å30.56 × 0.30 × 0.15 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer		6309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 25.1°, θmin = 3.2°
CCD scansh = −17→17
32329 measured reflectionsk = −22→22
8441 independent reflectionsl = −22→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0611P)2 + 0.0767P]
where P = (Fo2 + 2Fc2)/3
8441 reflections(Δ/σ)max = 0.001
595 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C26H23N2O3PSV = 4782.4 (6) Å3
Mr = 474.49Z = 8
Monoclinic, P21/nMo Kα radiation
a = 15.0419 (10) ŵ = 0.23 mm−1
b = 18.6355 (10) ÅT = 295 K
c = 18.5917 (18) Å0.56 × 0.30 × 0.15 mm
β = 113.413 (10)°
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer		6309 reflections with I > 2σ(I)
32329 measured reflectionsRint = 0.029
8441 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.04Δρmax = 0.25 e Å−3
8441 reflectionsΔρmin = −0.28 e Å−3
595 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.60435 (4)0.26549 (3)0.06832 (3)0.03823 (15)
P10.73384 (4)0.22036 (3)0.22228 (3)0.03282 (14)
O10.63908 (11)0.33781 (8)0.08560 (10)0.0540 (4)
O20.59940 (12)0.23771 (9)−0.00544 (8)0.0545 (4)
O30.15446 (12)0.38553 (10)0.01877 (11)0.0640 (5)
N10.66148 (12)0.20983 (9)0.13335 (10)0.0381 (4)
N20.19539 (13)0.26777 (10)0.03546 (10)0.0439 (5)
H20.17250.22590.03790.053*
C50.13239 (17)0.32332 (14)0.02196 (13)0.0492 (6)
C60.0322 (2)0.30213 (17)0.0123 (2)0.0857 (10)
H6A0.02950.29850.06290.128*
H6B0.01590.2566−0.01390.128*
H6C−0.01300.3378−0.01830.128*
C110.74745 (15)0.13304 (11)0.26552 (12)0.0364 (5)
C120.72650 (19)0.07279 (12)0.21875 (15)0.0559 (7)
H120.70560.07730.16470.067*
C130.7369 (2)0.00600 (13)0.25234 (19)0.0715 (8)
H130.7216−0.03460.22070.086*
C140.76928 (19)−0.00145 (13)0.33235 (17)0.0595 (7)
H140.7773−0.04690.35460.071*
C150.78979 (19)0.05756 (13)0.37871 (15)0.0576 (7)
H150.81140.05270.43280.069*
C160.77845 (18)0.12463 (12)0.34556 (13)0.0492 (6)
H160.79190.16500.37750.059*
C210.85231 (15)0.25325 (11)0.23595 (12)0.0372 (5)
C220.93602 (18)0.22040 (15)0.28608 (15)0.0589 (7)
H220.93220.17970.31360.071*
C231.02521 (19)0.24721 (17)0.29590 (17)0.0716 (8)
H231.08110.22410.32950.086*
C241.03252 (19)0.30698 (16)0.25716 (17)0.0641 (7)
H241.09300.32550.26470.077*
C250.9506 (2)0.33945 (15)0.20712 (18)0.0690 (8)
H250.95530.38020.18000.083*
C260.86062 (18)0.31328 (13)0.19594 (16)0.0562 (7)
H260.80520.33610.16110.067*
C310.68889 (15)0.27629 (11)0.27907 (12)0.0352 (5)
C320.59488 (17)0.26534 (13)0.27220 (14)0.0498 (6)
H320.55570.23210.23630.060*
C330.5591 (2)0.30353 (15)0.31856 (16)0.0621 (7)
H330.49610.29570.31420.074*
C340.6167 (2)0.35311 (14)0.37095 (15)0.0592 (7)
H340.59270.37890.40210.071*
C350.7090 (2)0.36480 (13)0.37737 (14)0.0578 (7)
H350.74730.39880.41270.069*
C360.74610 (18)0.32633 (12)0.33204 (13)0.0462 (6)
H360.80940.33420.33710.055*
C410.48472 (15)0.26548 (11)0.06320 (11)0.0345 (5)
C420.43550 (17)0.20264 (11)0.06204 (13)0.0442 (6)
H420.46670.15870.06680.053*
C430.34066 (17)0.20470 (11)0.05396 (13)0.0435 (5)
H430.30820.16220.05380.052*
C440.29302 (15)0.26972 (11)0.04594 (11)0.0368 (5)
C450.34292 (16)0.33258 (12)0.04923 (13)0.0438 (5)
H450.31230.37660.04570.053*
C460.43846 (16)0.32999 (11)0.05761 (13)0.0419 (5)
H460.47180.37250.05960.050*
S1'0.39565 (4)0.60029 (3)0.37549 (3)0.03796 (15)
P1'0.29976 (4)0.48985 (3)0.27043 (3)0.03572 (15)
O1'0.36387 (11)0.64762 (8)0.30907 (9)0.0540 (4)
O2'0.37677 (11)0.62497 (8)0.44208 (9)0.0499 (4)
O3'0.86803 (13)0.47540 (10)0.53859 (12)0.0703 (5)
N1'0.35642 (13)0.52178 (9)0.35569 (10)0.0399 (4)
N2'0.82514 (13)0.59181 (10)0.50987 (11)0.0456 (5)
H2'0.84950.63400.51220.055*
C03'0.0174 (2)0.52015 (17)0.12570 (19)0.0807 (10)
H23'−0.02410.50920.07450.097*
C5'0.89003 (17)0.53794 (15)0.54146 (13)0.0493 (6)
C6'0.99288 (18)0.56331 (16)0.58155 (16)0.0698 (8)
H6'11.02120.54290.63320.105*
H6'20.99400.61470.58530.105*
H6'31.02920.54840.55180.105*
C11'0.30394 (14)0.39466 (11)0.28443 (12)0.0348 (5)
C12'0.28480 (17)0.34757 (12)0.22329 (13)0.0475 (6)
H12'0.27320.36500.17350.057*
C13'0.28260 (19)0.27466 (13)0.23523 (14)0.0560 (7)
H13'0.26980.24310.19360.067*
C14'0.29939 (18)0.24874 (13)0.30821 (14)0.0531 (6)
H14'0.29780.19960.31610.064*
C15'0.31851 (19)0.29467 (13)0.36925 (14)0.0554 (7)
H15'0.32940.27670.41870.066*
C16'0.32181 (18)0.36738 (12)0.35837 (13)0.0492 (6)
H16'0.33600.39840.40060.059*
C21'0.17467 (16)0.51602 (12)0.23034 (13)0.0429 (5)
C22'0.11238 (18)0.49844 (14)0.15399 (16)0.0615 (7)
H22'0.13520.47220.12230.074*
C24'−0.0166 (2)0.55839 (19)0.1731 (2)0.0878 (10)
H24'−0.08080.57340.15350.105*
C25'0.0431 (2)0.57394 (18)0.2480 (2)0.0856 (10)
H25'0.01920.59860.28000.103*
C26'0.13908 (18)0.55348 (14)0.27692 (16)0.0609 (7)
H26'0.18000.56510.32810.073*
C31'0.35067 (17)0.51011 (12)0.19990 (13)0.0437 (5)
C32'0.43991 (19)0.48131 (15)0.21220 (17)0.0645 (7)
H32'0.46980.44990.25380.077*
C33'0.4851 (2)0.4989 (2)0.1627 (2)0.0864 (10)
H33'0.54540.47940.17140.104*
C34'0.4426 (3)0.5441 (2)0.1020 (2)0.0937 (12)
H34'0.47350.55530.06890.112*
C35'0.3549 (3)0.57337 (19)0.08893 (19)0.0904 (11)
H35'0.32590.60450.04700.108*
C36'0.3084 (2)0.55685 (15)0.13822 (16)0.0690 (8)
H36'0.24860.57730.12950.083*
C41'0.52275 (15)0.59244 (11)0.40911 (12)0.0336 (5)
C42'0.57060 (15)0.53071 (11)0.44354 (12)0.0355 (5)
H42'0.53520.49040.44550.043*
C43'0.67037 (16)0.52770 (11)0.47535 (12)0.0374 (5)
H43'0.70190.48530.49770.045*
C44'0.72346 (15)0.58761 (11)0.47384 (12)0.0361 (5)
C45'0.67459 (16)0.64967 (12)0.43796 (13)0.0430 (5)
H45'0.70980.69000.43580.052*
C46'0.57519 (16)0.65226 (12)0.40549 (12)0.0408 (5)
H46'0.54330.69400.38130.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0389 (3)0.0373 (3)0.0383 (3)0.0041 (2)0.0152 (2)0.0027 (2)
P10.0348 (3)0.0288 (3)0.0341 (3)0.0015 (2)0.0129 (2)−0.0013 (2)
O10.0462 (10)0.0352 (9)0.0782 (12)−0.0018 (7)0.0221 (8)0.0049 (8)
O20.0603 (11)0.0717 (11)0.0345 (8)0.0177 (9)0.0221 (8)0.0050 (8)
O30.0454 (11)0.0511 (11)0.0861 (13)0.0109 (9)0.0160 (9)0.0114 (10)
N10.0396 (11)0.0365 (10)0.0349 (10)0.0054 (8)0.0113 (8)−0.0015 (8)
N20.0400 (11)0.0431 (11)0.0482 (11)−0.0026 (9)0.0170 (9)0.0012 (9)
C50.0395 (14)0.0572 (16)0.0450 (14)0.0049 (13)0.0104 (11)0.0061 (12)
C60.0487 (18)0.086 (2)0.122 (3)0.0049 (16)0.0332 (18)0.009 (2)
C110.0347 (12)0.0310 (11)0.0430 (12)0.0026 (9)0.0149 (10)−0.0007 (10)
C120.0745 (19)0.0366 (13)0.0501 (15)0.0027 (13)0.0178 (13)−0.0059 (11)
C130.090 (2)0.0291 (14)0.085 (2)0.0007 (14)0.0236 (18)−0.0074 (14)
C140.0590 (17)0.0377 (14)0.077 (2)0.0026 (12)0.0215 (15)0.0157 (13)
C150.0685 (18)0.0488 (16)0.0534 (15)0.0060 (13)0.0220 (13)0.0142 (13)
C160.0641 (17)0.0369 (13)0.0426 (13)0.0002 (12)0.0169 (12)0.0032 (11)
C210.0369 (13)0.0368 (12)0.0389 (12)0.0020 (10)0.0162 (10)−0.0053 (10)
C220.0427 (15)0.0688 (18)0.0598 (16)−0.0004 (13)0.0146 (13)0.0184 (14)
C230.0377 (16)0.095 (2)0.0728 (19)0.0017 (15)0.0120 (14)0.0172 (17)
C240.0409 (16)0.080 (2)0.0736 (19)−0.0127 (14)0.0248 (14)−0.0107 (16)
C250.0576 (19)0.0526 (16)0.100 (2)−0.0094 (14)0.0350 (17)0.0108 (16)
C260.0421 (15)0.0423 (14)0.0804 (18)0.0015 (11)0.0203 (13)0.0119 (13)
C310.0427 (13)0.0300 (11)0.0331 (11)0.0034 (10)0.0151 (10)0.0008 (9)
C320.0465 (15)0.0543 (15)0.0506 (14)−0.0021 (12)0.0214 (12)−0.0123 (12)
C330.0537 (17)0.0761 (19)0.0657 (17)0.0099 (14)0.0336 (14)−0.0046 (15)
C340.084 (2)0.0533 (16)0.0495 (15)0.0160 (15)0.0357 (15)−0.0042 (12)
C350.082 (2)0.0431 (14)0.0485 (15)−0.0036 (13)0.0263 (14)−0.0140 (12)
C360.0547 (15)0.0374 (13)0.0479 (14)−0.0033 (11)0.0218 (12)−0.0064 (11)
C410.0376 (12)0.0326 (12)0.0310 (11)0.0018 (10)0.0110 (9)−0.0007 (9)
C420.0477 (15)0.0297 (12)0.0518 (14)0.0052 (10)0.0162 (11)−0.0008 (10)
C430.0452 (14)0.0321 (12)0.0518 (14)−0.0049 (10)0.0176 (11)0.0000 (10)
C440.0356 (12)0.0425 (13)0.0293 (11)0.0003 (10)0.0097 (9)0.0001 (10)
C450.0480 (14)0.0321 (12)0.0547 (14)0.0063 (11)0.0240 (12)0.0057 (10)
C460.0449 (14)0.0313 (12)0.0513 (14)−0.0017 (10)0.0210 (11)0.0020 (10)
S1'0.0363 (3)0.0317 (3)0.0452 (3)0.0027 (2)0.0155 (2)−0.0002 (2)
P1'0.0336 (3)0.0361 (3)0.0358 (3)0.0005 (2)0.0120 (2)0.0008 (2)
O1'0.0474 (10)0.0444 (10)0.0613 (11)0.0077 (8)0.0123 (8)0.0164 (8)
O2'0.0499 (10)0.0455 (9)0.0630 (10)−0.0013 (8)0.0318 (8)−0.0155 (8)
O3'0.0495 (11)0.0474 (11)0.1054 (16)0.0086 (9)0.0216 (10)0.0047 (10)
N1'0.0435 (11)0.0343 (10)0.0388 (10)−0.0022 (8)0.0131 (8)−0.0006 (8)
N2'0.0366 (11)0.0444 (11)0.0549 (12)−0.0016 (9)0.0174 (9)0.0056 (9)
C03'0.0468 (18)0.084 (2)0.080 (2)0.0057 (16)−0.0078 (16)0.0192 (18)
C5'0.0418 (15)0.0585 (17)0.0466 (14)0.0058 (13)0.0166 (11)−0.0009 (12)
C6'0.0415 (16)0.080 (2)0.078 (2)0.0046 (15)0.0131 (14)−0.0015 (16)
C11'0.0310 (11)0.0374 (12)0.0349 (11)−0.0026 (9)0.0119 (9)−0.0030 (9)
C12'0.0583 (16)0.0457 (14)0.0362 (12)−0.0105 (12)0.0164 (11)−0.0010 (10)
C13'0.0768 (19)0.0414 (14)0.0445 (14)−0.0163 (13)0.0185 (13)−0.0119 (11)
C14'0.0650 (17)0.0378 (13)0.0519 (15)−0.0100 (12)0.0183 (13)−0.0007 (12)
C15'0.0785 (19)0.0460 (15)0.0393 (13)−0.0033 (13)0.0210 (13)0.0074 (11)
C16'0.0684 (17)0.0405 (13)0.0370 (13)−0.0005 (12)0.0192 (12)−0.0059 (10)
C21'0.0363 (13)0.0423 (13)0.0479 (14)0.0040 (10)0.0145 (11)0.0066 (11)
C22'0.0469 (16)0.0644 (18)0.0604 (17)0.0041 (13)0.0078 (13)−0.0002 (13)
C24'0.0404 (17)0.095 (3)0.120 (3)0.0178 (17)0.0229 (19)0.020 (2)
C25'0.058 (2)0.102 (3)0.105 (3)0.0288 (19)0.041 (2)0.011 (2)
C26'0.0495 (16)0.0701 (18)0.0644 (17)0.0122 (14)0.0240 (13)0.0032 (14)
C31'0.0496 (14)0.0414 (13)0.0436 (13)−0.0076 (11)0.0224 (11)−0.0033 (10)
C32'0.0516 (17)0.0740 (19)0.0761 (19)−0.0051 (14)0.0341 (15)−0.0010 (15)
C33'0.070 (2)0.107 (3)0.106 (3)−0.021 (2)0.061 (2)−0.021 (2)
C34'0.124 (3)0.101 (3)0.090 (3)−0.052 (3)0.078 (3)−0.025 (2)
C35'0.131 (3)0.089 (2)0.068 (2)−0.014 (2)0.058 (2)0.0175 (18)
C36'0.087 (2)0.0662 (18)0.0634 (18)0.0045 (16)0.0396 (16)0.0163 (15)
C41'0.0374 (12)0.0333 (11)0.0335 (11)0.0008 (9)0.0178 (9)−0.0021 (9)
C42'0.0404 (13)0.0269 (11)0.0416 (12)−0.0018 (9)0.0190 (10)−0.0027 (9)
C43'0.0420 (13)0.0318 (12)0.0410 (12)0.0058 (10)0.0193 (10)0.0011 (9)
C44'0.0359 (12)0.0413 (13)0.0348 (11)0.0009 (10)0.0178 (10)0.0019 (9)
C45'0.0401 (13)0.0415 (13)0.0527 (14)−0.0026 (11)0.0239 (11)0.0093 (11)
C46'0.0451 (14)0.0353 (12)0.0450 (13)0.0052 (10)0.0210 (11)0.0106 (10)
Geometric parameters (Å, º) top
S1—O11.4348 (16)S1'—O1'1.4361 (15)
S1—O21.4398 (15)S1'—O2'1.4506 (15)
S1—N11.5655 (17)S1'—N1'1.5658 (18)
S1—C411.764 (2)S1'—C41'1.766 (2)
P1—N11.5896 (18)P1'—N1'1.5872 (18)
P1—C111.790 (2)P1'—C11'1.790 (2)
P1—C311.796 (2)P1'—C21'1.794 (2)
P1—C211.804 (2)P1'—C31'1.802 (2)
O3—C51.214 (3)O3'—C5'1.207 (3)
N2—C51.358 (3)N2'—C5'1.360 (3)
N2—C441.403 (3)N2'—C44'1.407 (3)
N2—H20.8605N2'—H2'0.8606
C5—C61.498 (3)C03'—C22'1.373 (4)
C6—H6A0.9600C03'—C24'1.379 (5)
C6—H6B0.9600C03'—H23'0.9300
C6—H6C0.9600C5'—C6'1.502 (3)
C11—C161.380 (3)C6'—H6'10.9600
C11—C121.378 (3)C6'—H6'20.9600
C12—C131.373 (3)C6'—H6'30.9600
C12—H120.9300C11'—C12'1.373 (3)
C13—C141.376 (4)C11'—C16'1.388 (3)
C13—H130.9300C12'—C13'1.379 (3)
C14—C151.355 (3)C12'—H12'0.9300
C14—H140.9300C13'—C14'1.366 (3)
C15—C161.374 (3)C13'—H13'0.9300
C15—H150.9300C14'—C15'1.358 (3)
C16—H160.9300C14'—H14'0.9300
C21—C221.377 (3)C15'—C16'1.374 (3)
C21—C261.376 (3)C15'—H15'0.9300
C22—C231.374 (3)C16'—H16'0.9300
C22—H220.9300C21'—C26'1.376 (3)
C23—C241.354 (4)C21'—C22'1.394 (3)
C23—H230.9300C22'—H22'0.9300
C24—C251.357 (4)C24'—C25'1.355 (5)
C24—H240.9300C24'—H24'0.9300
C25—C261.374 (3)C25'—C26'1.379 (4)
C25—H250.9300C25'—H25'0.9300
C26—H260.9300C26'—H26'0.9300
C31—C321.384 (3)C31'—C32'1.378 (3)
C31—C361.381 (3)C31'—C36'1.378 (3)
C32—C331.381 (3)C32'—C33'1.383 (4)
C32—H320.9300C32'—H32'0.9300
C33—C341.372 (4)C33'—C34'1.349 (5)
C33—H330.9300C33'—H33'0.9300
C34—C351.362 (4)C34'—C35'1.357 (5)
C34—H340.9300C34'—H34'0.9300
C35—C361.382 (3)C35'—C36'1.390 (4)
C35—H350.9300C35'—H35'0.9300
C36—H360.9300C36'—H36'0.9300
C41—C461.372 (3)C41'—C42'1.373 (3)
C41—C421.381 (3)C41'—C46'1.383 (3)
C42—C431.374 (3)C42'—C43'1.378 (3)
C42—H420.9300C42'—H42'0.9300
C43—C441.385 (3)C43'—C44'1.379 (3)
C43—H430.9300C43'—H43'0.9300
C44—C451.379 (3)C44'—C45'1.390 (3)
C45—C461.383 (3)C45'—C46'1.373 (3)
C45—H450.9300C45'—H45'0.9300
C46—H460.9300C46'—H46'0.9300
O1—S1—O2115.31 (10)O1'—S1'—O2'115.34 (10)
O1—S1—N1114.21 (10)O1'—S1'—N1'113.96 (10)
O2—S1—N1107.58 (9)O2'—S1'—N1'108.28 (9)
O1—S1—C41106.56 (10)O1'—S1'—C41'107.39 (10)
O2—S1—C41106.44 (10)O2'—S1'—C41'106.02 (9)
N1—S1—C41106.06 (10)N1'—S1'—C41'105.05 (10)
N1—P1—C11105.29 (9)N1'—P1'—C11'104.62 (9)
N1—P1—C31114.90 (9)N1'—P1'—C21'111.80 (10)
C11—P1—C31105.43 (9)C11'—P1'—C21'107.47 (10)
N1—P1—C21114.72 (9)N1'—P1'—C31'115.68 (10)
C11—P1—C21108.37 (10)C11'—P1'—C31'108.23 (10)
C31—P1—C21107.54 (10)C21'—P1'—C31'108.63 (11)
S1—N1—P1131.33 (11)S1'—N1'—P1'126.00 (11)
C5—N2—C44128.4 (2)C5'—N2'—C44'128.5 (2)
C5—N2—H2115.8C5'—N2'—H2'115.7
C44—N2—H2115.8C44'—N2'—H2'115.8
O3—C5—N2123.6 (2)C22'—C03'—C24'120.1 (3)
O3—C5—C6121.8 (2)C22'—C03'—H23'120.0
N2—C5—C6114.6 (2)C24'—C03'—H23'119.9
C5—C6—H6A109.5O3'—C5'—N2'123.8 (2)
C5—C6—H6B109.6O3'—C5'—C6'122.4 (2)
H6A—C6—H6B109.5N2'—C5'—C6'113.8 (2)
C5—C6—H6C109.3C5'—C6'—H6'1109.4
H6A—C6—H6C109.5C5'—C6'—H6'2109.6
H6B—C6—H6C109.5H6'1—C6'—H6'2109.5
C16—C11—C12118.8 (2)C5'—C6'—H6'3109.5
C16—C11—P1121.12 (17)H6'1—C6'—H6'3109.5
C12—C11—P1120.04 (17)H6'2—C6'—H6'3109.5
C13—C12—C11119.7 (2)C12'—C11'—C16'118.7 (2)
C13—C12—H12120.1C12'—C11'—P1'121.96 (16)
C11—C12—H12120.2C16'—C11'—P1'119.25 (16)
C12—C13—C14120.7 (3)C11'—C12'—C13'120.5 (2)
C12—C13—H13119.7C11'—C12'—H12'119.7
C14—C13—H13119.6C13'—C12'—H12'119.8
C15—C14—C13119.9 (2)C14'—C13'—C12'120.1 (2)
C15—C14—H14120.0C14'—C13'—H13'119.9
C13—C14—H14120.0C12'—C13'—H13'120.0
C14—C15—C16119.8 (2)C15'—C14'—C13'120.1 (2)
C14—C15—H15120.2C15'—C14'—H14'120.0
C16—C15—H15120.0C13'—C14'—H14'119.9
C15—C16—C11121.0 (2)C14'—C15'—C16'120.4 (2)
C15—C16—H16119.5C14'—C15'—H15'119.7
C11—C16—H16119.4C16'—C15'—H15'119.9
C22—C21—C26118.2 (2)C15'—C16'—C11'120.2 (2)
C22—C21—P1122.05 (18)C15'—C16'—H16'119.9
C26—C21—P1119.78 (17)C11'—C16'—H16'119.9
C23—C22—C21120.7 (2)C26'—C21'—C22'119.2 (2)
C23—C22—H22119.6C26'—C21'—P1'118.85 (18)
C21—C22—H22119.7C22'—C21'—P1'121.92 (19)
C24—C23—C22120.6 (3)C03'—C22'—C21'119.8 (3)
C24—C23—H23119.7C03'—C22'—H22'120.1
C22—C23—H23119.7C21'—C22'—H22'120.1
C23—C24—C25119.2 (3)C25'—C24'—C03'120.3 (3)
C23—C24—H24120.4C25'—C24'—H24'119.8
C25—C24—H24120.4C03'—C24'—H24'119.9
C24—C25—C26121.2 (3)C24'—C25'—C26'120.3 (3)
C24—C25—H25119.4C24'—C25'—H25'119.8
C26—C25—H25119.4C26'—C25'—H25'119.8
C25—C26—C21120.1 (2)C21'—C26'—C25'120.2 (3)
C25—C26—H26119.9C21'—C26'—H26'119.8
C21—C26—H26119.9C25'—C26'—H26'119.9
C32—C31—C36119.3 (2)C32'—C31'—C36'118.8 (2)
C32—C31—P1118.03 (16)C32'—C31'—P1'117.74 (19)
C36—C31—P1122.53 (17)C36'—C31'—P1'123.3 (2)
C33—C32—C31120.2 (2)C31'—C32'—C33'120.1 (3)
C33—C32—H32119.9C31'—C32'—H32'120.0
C31—C32—H32119.8C33'—C32'—H32'119.9
C34—C33—C32119.8 (2)C34'—C33'—C32'120.7 (3)
C34—C33—H33120.1C34'—C33'—H33'119.6
C32—C33—H33120.1C32'—C33'—H33'119.7
C35—C34—C33120.3 (2)C33'—C34'—C35'120.3 (3)
C35—C34—H34119.9C33'—C34'—H34'119.9
C33—C34—H34119.9C35'—C34'—H34'119.8
C34—C35—C36120.5 (2)C34'—C35'—C36'120.1 (3)
C34—C35—H35119.7C34'—C35'—H35'119.9
C36—C35—H35119.8C36'—C35'—H35'120.0
C31—C36—C35119.8 (2)C31'—C36'—C35'120.1 (3)
C31—C36—H36120.1C31'—C36'—H36'120.0
C35—C36—H36120.1C35'—C36'—H36'119.9
C46—C41—C42119.3 (2)C42'—C41'—C46'119.7 (2)
C46—C41—S1118.67 (16)C42'—C41'—S1'121.85 (16)
C42—C41—S1122.01 (16)C46'—C41'—S1'118.32 (16)
C43—C42—C41120.3 (2)C41'—C42'—C43'120.91 (19)
C43—C42—H42119.8C41'—C42'—H42'119.5
C41—C42—H42119.8C43'—C42'—H42'119.5
C42—C43—C44120.4 (2)C44'—C43'—C42'119.9 (2)
C42—C43—H43119.8C44'—C43'—H43'120.0
C44—C43—H43119.8C42'—C43'—H43'120.1
C45—C44—C43119.3 (2)C43'—C44'—C45'118.9 (2)
C45—C44—N2123.3 (2)C43'—C44'—N2'124.32 (19)
C43—C44—N2117.41 (19)C45'—C44'—N2'116.72 (19)
C44—C45—C46119.9 (2)C46'—C45'—C44'121.1 (2)
C44—C45—H45120.0C46'—C45'—H45'119.5
C46—C45—H45120.1C44'—C45'—H45'119.4
C41—C46—C45120.8 (2)C45'—C46'—C41'119.5 (2)
C41—C46—H46119.6C45'—C46'—H46'120.3
C45—C46—H46119.6C41'—C46'—H46'120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2′i0.862.112.966 (2)173
N2′—H2′···O2ii0.862.112.961 (2)174
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC26H23N2O3PS
Mr474.49
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)15.0419 (10), 18.6355 (10), 18.5917 (18)
β (°) 113.413 (10)
V (Å3)4782.4 (6)
Z8
Radiation typeMo Kα
µ (mm−1)0.23
Crystal size (mm)0.56 × 0.30 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		32329, 8441, 6309
Rint0.029
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.106, 1.04
No. of reflections8441
No. of parameters595
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.25, −0.28

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2'i0.86002.11002.966 (2)173.00
N2'—H2'···O2ii0.86002.11002.961 (2)174.00
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.
 

Footnotes

‡Present address: Astex Therapeutics, 436 Cambridge Science Park, Cambridge CB4 0QA, England.

Acknowledgements

The authors thank the Ministry of Science and Technology of the Republic of Croatia for partial financial support of this work (grant Nos. 0006543 and 0119632).

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ISSN: 2056-9890
Volume 66| Part 5| May 2010| Pages o1098-o1099
https://doi.org/10.1107/S1600536810013620
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