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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1098–o1099.
Published online 2010 April 17. doi:  10.1107/S1600536810013620
PMCID: PMC2979042

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

Abstract

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

An external file that holds a picture, illustration, etc.
Object name is e-66-o1098-scheme1.jpg

Experimental

Crystal data

  • C26H23N2O3PS
  • M r = 474.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1098-efi5.jpg
  • 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)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013620/bg2337Isup2.hkl

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.
View of the molecule I with the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Overlaped structures of independent molecules of compound I, showing structural differences.
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) ...
Fig. 4.
Synthetic route to the molecule I.

Crystal data

C26H23N2O3PSF(000) = 1984
Mr = 474.49Dx = 1.318 Mg m3
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 mm1
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

Oxford Diffraction Xcalibur CCD diffractometer6309 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 25.1°, θmin = 3.2°
CCD scansh = −17→17
32329 measured reflectionsk = −22→22
8441 independent reflectionsl = −22→21

Refinement

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 = 1.04w = 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 Å3
0 restraintsΔρmin = −0.28 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2337).

References

  • Andersen, N. G., Parvez, M., McDonald, R. & Keay, B. A. (2004). Can. J. Chem.82, 145–7161.
  • Andersen, N. G., Ramsden, P. D., Che, D., Parvez, M. & Keay, B. A. (1999). Org. Lett.1, 2009–2011.
  • Andersen, N. G., Ramsden, P. D., Che, D., Parvez, M. & Keay, B. A. (2001). J. Org. Chem.66, 7478–7486. [PubMed]
  • Ashley, J. N., Buchanan, G. L. & Easson, A. P. T. (1947). J. Chem. Soc. pp. 60–67.
  • Dumić, M., Filić, D., Vinković, M., Jamnicky, B. & Kamenar, B. (1993). Tetrahedron Lett.34, 3639–3642.
  • Dumić, M., Vinković, M., Filić, D., Jamnicky, B., Eškinja, M. & Kamenar, B. (1995). J. Med. Chem.38, 3034–3042. [PubMed]
  • Filić, D., Vinković, M., Jamnicky, B. & Dumić, M. (1996). Croat. Chem. Acta, 69, 631–641.
  • Khmel’nitzkaya, I. & Mikhel’s, V. (1934). Zh. Obshch. Khim. pp. 452–455.
  • Matano, Y., Nomura, H. & Suzuki, H. (2002). Inorg. Chem.41, 1940–1948. [PubMed]
  • Monkowius, U. V., Nogai, S. & Schmidbaur, H. (2004). Dalton Trans. pp. 1610–1617. [PubMed]
  • Orešić, M., Filić, D., Prugovečki, B., Vinković, M. & Dumić, M. (2001). Croat. Chem. Acta, 74, 667–682.
  • Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Prugovečki, B., Marinković, M., Vinković, M. & Dumić, M. (2005). Acta Cryst. E61, o2844–o2846.
  • Prugovečki, B., Marinković, M., Vinković, M. & Dumić, M. (2006). Croat. Chem. Acta, 79, 219–226.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Vinković, M., Dumić, M. & Kamenar, B. (1993). Acta Cryst. C49, 1661–1663.
  • Žegarac, M., Marinković, M., Prugovečki, B., Vinković, M. & Dumić, M. (2010). In preparation. [PMC free article] [PubMed]
  • Zhu, S., Xu, B., Qin, C. & Xu, G. (1997). Inorg. Chem.36, 4909–4911. [PubMed]

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