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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 12| December 2012| Pages o3491-o3492

N,N-Bis(di­phenyl­thio­phosphino­yl)-4-ethyl­aniline

aDepartment of Chemistry, University of Fort Hare, Private Bag X1314, Alice 5700, South Africa, and bSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
*Correspondence e-mail: owaga@ukzn.ac.za

(Received 6 November 2012; accepted 26 November 2012; online 30 November 2012)

The title compound, C32H29NP2S2, has two mol­ecules in the asymmetric unit, with an r.m.s. difference of 0.218 Å in their best-fit overlay. Both mol­ecules have a slightly distorted trigonal–planar N atom, bonded to two PV atoms and a C atom of the 4-ethyl­phenyl unit. The P—N—P angles of 126.34 (11) and 125.98 (11)° are larger than the four C—N—P bond angles. The two S atoms are trans to one another with respect to the P—N—P angle. The crystal structure features C—H⋯π inter­actions. The methyl group in one of the mol­ecules is disordered over two sets of sites, with occupancies of 0.518 (6) and 0.482 (6).

Related literature

For background to the chemistry of coordination compounds containing P—N bonds and for their applications, see: Hartley (1990[Hartley, F. R. (1990). The Chemistry of Organophosphorus Compounds, p. 1. Manchester: Wiley.]); Greenwood & Earnshaw (1984[Greenwood, N. N. & Earnshaw, A. (1984). Chemistry of Elements, p. 619. Oxford: Pergamon Press.]); Balakrishna et al. (2000[Balakrishna, M. S., Panda, R., Smith, D. C. Jr, Kalamn, A. & Nolan, S. P. (2000). J. Organomet. Chem. 599, 159-165.]). For the ability of bis­(diphenyl­phosphino)alkyl­aniline derivatives to form chelates with transition metal ions, see: Biricik et al. (2007)[Biricik, N., Durap, F., Gümgüm, B., Fei, Z. & Scopelliti, R. (2007). Transition Met. Chem. 32, 877-883.]; Fei & Dyson (2005[Fei, Z. & Dyson, P. J. (2005). Coord. Chem. Rev. 249, 2056-2074.]). For the synthesis of the title and related compounds, see: Fernández et al. (2005[Fernández, I., Breher, F., Pregosin, P. S., Fei, Z. & Dyson, P. J. (2005). Inorg. Chem. 44, 7616-7623.]); Gaw et al. (2002[Gaw, K. G., Smith, M. B. & Steed, J. W. (2002). J. Organomet. Chem. 664, 294-297.]); Fei et al. (2004[Fei, Z., Zhao, D., Biricik, N., Scopelliti, R. & Dyson, P. J. (2004). Inorg. Chem. 44, 2228-2230.]); Slawin et al. (2005[Slawin, A. M. Z., Wheatley, J. & Woollins, J. D. (2005). Eur. J. Inorg. Chem. pp. 713-720.]).

[Scheme 1]

Experimental

Crystal data
  • C32H29NP2S2

  • Mr = 553.62

  • Triclinic, [P \overline 1]

  • a = 9.6305 (11) Å

  • b = 13.8027 (14) Å

  • c = 21.360 (2) Å

  • α = 82.484 (2)°

  • β = 84.635 (2)°

  • γ = 79.975 (2)°

  • V = 2764.7 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 173 K

  • 0.17 × 0.08 × 0.08 mm

Data collection
  • Bruker X8 APEXII 4K KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.946, Tmax = 0.974

  • 56725 measured reflections

  • 13522 independent reflections

  • 9271 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.107

  • S = 1.00

  • 13522 reflections

  • 684 parameters

  • 9 restraints

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19–C24 and C57–C62 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17⋯Cg2i 0.95 2.97 3.759 (3) 141
C64—H64ACg1ii 0.98 2.88 3.767 (3) 151
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y, z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

Compounds containing P—N bonds have been known for many years and their chemistry has been of considerable interest because of their applications in increasingly diverse fields (Hartley, 1990; Greenwood & Earnshaw, 1984) and in homogeneous catalysis as these ligands can be used for fine tuning the activity and selectivity of the catalyst (Balakrishna et al., 2000). Bis(diphenylphosphino)alkylaniline derivatives are of particular interest among amino phosphines due to their stability and ability to form chelates with transition metal ions (Biricik et al., 2007; Fei & Dyson, 2005). Synthesis of bis(diphenylphosphino)alkylaniline is through aminolysis of aniline (Fernández et al., 2005; Gaw et al., 2002) and incorporation of additional functional groups (Fei et al., 2004; Slawin et al., 2005).

The structure of (I) Fig. 1, has a slightly distorted trigonal planar N atom bound to two PV atoms and a C atom of the p-ethylphenyl moiety in which the P–N–P angle is larger, 126.01 (11) and 126.28 (11)°, than the four C–N–P bond angles in the two molecules (between 116.03(13 and 117.10 (13) Å). The two S atoms are trans to one another with respect to the trigonal plane. The P–N bond distances 1.7162 (18), 1.7192 (18), 1.7134 (17) and 1.7212 (18) Å and P–S bond distances 1.9469 (8), 1.9468 (8), 1.9446 (8) and 1.9449 (8) Å are similar in both molecules and compare well to those of similar molecules in literature (Slawin et al., 2005). The r.m.s. value of an overlay of the two molecules is 0.218 Å and shows major differences only between the ethyl moieties of the two molecules. The crystal lattice is stabilized by two C—H···π intermolecular interactions with Cg···H distances of 3.759 (3) and 3.767 (3) Å.

Related literature top

For background to the chemistry of coordination compounds containing P—N bonds and for their applications, see: Hartley (1990); Greenwood & Earnshaw (1984); Balakrishna et al. (2000). For the ability of bis(diphenylphosphino)alkylaniline derivatives to form chelates with transition metal ions, see: Biricik et al., 2007; Fei & Dyson, 2005). For the synthesis of the title and related compounds, see: Fernández et al. (2005); Gaw et al. (2002); Fei et al. (2004); Slawin et al. (2005).

Experimental top

N,N-Bis(diphenylphosphino)ethylaniline is prepared by the aminolysis reaction of H2NC6H4—C2H5(4-C2H5) with two equivalents of Ph2PCl according to the procedure given in the literature (Hartley, 1990). Solid N,N-bis(diphenylphosphino)ethylaniline (0.20 g, 0.420 mmol) and S8 (0.027 g, 0.840 mmol) were dissolved in 20 ml of tetrahydrofuran and refluxed for 6 h. The volume was concentrated in vacuo to about 2 ml follow by the addition of 20 ml n-hexane to give [(Ph2P(S)2N—C6H4(C2H5)] as a white solid. Recrystallization in chloroform hexane gave crystals suitable for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Overlay structure of the two molecules in the asymmetric unit.
N,N-Bis(diphenylthiophosphinoyl)-4-ethylaniline top
Crystal data top
C32H29NP2S2Z = 4
Mr = 553.62F(000) = 1160
Triclinic, P1Dx = 1.33 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6305 (11) ÅCell parameters from 56725 reflections
b = 13.8027 (14) Åθ = 1.0–28.2°
c = 21.360 (2) ŵ = 0.33 mm1
α = 82.484 (2)°T = 173 K
β = 84.635 (2)°Needle, colourless
γ = 79.975 (2)°0.17 × 0.08 × 0.08 mm
V = 2764.7 (5) Å3
Data collection top
Bruker X8 APEXII 4K KappaCCD
diffractometer
9271 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ and ω scansθmax = 28.2°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1212
Tmin = 0.946, Tmax = 0.974k = 1818
56725 measured reflectionsl = 2828
13522 independent reflections
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0442P)2 + 1.5667P]
where P = (Fo2 + 2Fc2)/3
13522 reflections(Δ/σ)max = 0.001
684 parametersΔρmax = 0.82 e Å3
9 restraintsΔρmin = 0.36 e Å3
Crystal data top
C32H29NP2S2γ = 79.975 (2)°
Mr = 553.62V = 2764.7 (5) Å3
Triclinic, P1Z = 4
a = 9.6305 (11) ÅMo Kα radiation
b = 13.8027 (14) ŵ = 0.33 mm1
c = 21.360 (2) ÅT = 173 K
α = 82.484 (2)°0.17 × 0.08 × 0.08 mm
β = 84.635 (2)°
Data collection top
Bruker X8 APEXII 4K KappaCCD
diffractometer
13522 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
9271 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.974Rint = 0.054
56725 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0429 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.00Δρmax = 0.82 e Å3
13522 reflectionsΔρmin = 0.36 e Å3
684 parameters
Special details top

Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.98 Å for Me H atoms, 0.99 Å for Methylene H atoms and 0.95 for aromatic H atoms; Uiso(H) = 1.2Ueq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation. Disorder: Disorder was found for one ethyl group in the p-ethylpyridyl moiety, which is not an uncommon situation. The disorder was modelled for C– and H– atoms using distance restraints and constraints, and PART instructions and the total occupancy was kept as 1 during the refinement. The carbon atom involved in disorder were modelled with anisotropic thermal parameters. The occupancy of the C atoms in the disordered ethyl moiety was fixed at 50:50 during the refinement.

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
xyzUiso*/UeqOcc. (<1)
C10.5587 (2)0.33146 (16)0.20639 (10)0.0147 (4)
C20.4212 (2)0.31222 (16)0.22027 (10)0.0158 (4)
H20.3890.26430.19960.019*
C30.3308 (2)0.36277 (17)0.26418 (11)0.0180 (5)
H30.23710.34930.27330.022*
C40.3767 (2)0.43249 (17)0.29454 (11)0.0184 (5)
H40.31490.46660.32470.022*
C50.5134 (2)0.45267 (16)0.28089 (11)0.0178 (5)
H50.54490.50070.30180.021*
C60.6041 (2)0.40305 (16)0.23693 (11)0.0170 (5)
H60.69720.41760.22750.02*
C70.6830 (2)0.35878 (16)0.07850 (11)0.0163 (4)
C80.6379 (2)0.34382 (18)0.02078 (11)0.0202 (5)
H80.6030.28480.01690.024*
C90.6443 (2)0.4158 (2)0.03108 (12)0.0258 (5)
H90.61490.40510.07050.031*
C100.6929 (2)0.50268 (19)0.02589 (12)0.0269 (6)
H100.69650.55150.06150.032*
C110.7366 (2)0.51829 (18)0.03159 (12)0.0241 (5)
H110.76940.57820.03540.029*
C120.7326 (2)0.44653 (17)0.08364 (11)0.0198 (5)
H120.76370.45720.12270.024*
C131.0769 (2)0.10323 (16)0.16047 (10)0.0138 (4)
C140.9979 (2)0.02726 (16)0.17924 (10)0.0152 (4)
H140.89760.04110.18010.018*
C151.0657 (2)0.06832 (17)0.19667 (11)0.0176 (5)
H151.01180.11950.21080.021*
C161.2126 (2)0.08925 (17)0.19343 (11)0.0199 (5)
H161.25890.1550.20470.024*
C171.2917 (2)0.01454 (18)0.17376 (11)0.0193 (5)
H171.39210.02930.17120.023*
C181.2246 (2)0.08165 (17)0.15790 (10)0.0160 (4)
H181.27890.1330.14520.019*
C190.9629 (2)0.22248 (17)0.05160 (10)0.0151 (4)
C200.9154 (2)0.14218 (17)0.03165 (11)0.0172 (5)
H200.89170.08950.06180.021*
C210.9029 (2)0.13954 (18)0.03239 (11)0.0212 (5)
H210.86960.08550.0460.025*
C220.9392 (2)0.21577 (19)0.07646 (12)0.0253 (5)
H220.930.21390.12020.03*
C230.9888 (2)0.29476 (19)0.05695 (11)0.0233 (5)
H231.01490.34630.08740.028*
C241.0002 (2)0.29855 (17)0.00685 (11)0.0178 (5)
H241.03350.35290.02010.021*
C250.8366 (2)0.21872 (17)0.24500 (10)0.0159 (4)
C260.7654 (2)0.14545 (17)0.27729 (11)0.0212 (5)
H260.71770.10830.25440.025*
C270.7638 (3)0.12657 (19)0.34268 (12)0.0271 (6)
H270.71310.07730.36410.033*
C280.8352 (2)0.1784 (2)0.37793 (12)0.0280 (6)
C290.9056 (2)0.2508 (2)0.34481 (12)0.0268 (6)
H290.95490.28710.36760.032*
C300.9065 (2)0.27200 (18)0.27942 (11)0.0201 (5)
H300.95480.32270.25820.024*
C31A0.8203 (5)0.1365 (5)0.4457 (3)0.0251 (14)0.482 (6)
H31A0.84630.06340.45030.03*0.482 (6)
H31B0.7220.15420.46370.03*0.482 (6)
C32A0.9219 (6)0.1829 (4)0.4788 (3)0.0328 (16)0.482 (6)
H32A1.01750.16810.45850.049*0.482 (6)
H32B0.92170.15550.52350.049*0.482 (6)
H32C0.89160.25480.47560.049*0.482 (6)
C32B0.9574 (6)0.0888 (6)0.4745 (3)0.072 (3)0.518 (6)
H32D0.94760.02550.46060.108*0.518 (6)
H32E0.95220.08240.52090.108*0.518 (6)
H32F1.04870.10680.45760.108*0.518 (6)
C31B0.8439 (6)0.1653 (4)0.4514 (3)0.0204 (15)*0.518 (6)
H31C0.85680.22920.46460.025*0.518 (6)
H31D0.75280.14930.47190.025*0.518 (6)
C330.0832 (2)0.32778 (16)0.71094 (10)0.0136 (4)
C340.1283 (2)0.39978 (16)0.74106 (11)0.0180 (5)
H340.22230.41290.73250.022*
C350.0356 (2)0.45200 (17)0.78348 (11)0.0182 (5)
H350.06680.50030.80420.022*
C360.1018 (2)0.43402 (17)0.79578 (11)0.0181 (5)
H360.16460.46980.82490.022*
C370.1477 (2)0.36362 (17)0.76552 (11)0.0179 (5)
H370.24240.35170.77360.022*
C380.0557 (2)0.31046 (16)0.72330 (10)0.0148 (4)
H380.08750.26220.70280.018*
C390.1969 (2)0.35422 (16)0.58254 (11)0.0162 (5)
C400.1467 (2)0.33689 (18)0.52653 (11)0.0197 (5)
H400.11470.27620.52420.024*
C410.1434 (2)0.4083 (2)0.47428 (12)0.0269 (6)
H410.11030.39590.4360.032*
C420.1880 (2)0.4973 (2)0.47764 (13)0.0303 (6)
H420.18530.5460.44170.036*
C430.2364 (2)0.51555 (18)0.53309 (13)0.0274 (6)
H430.26650.57690.53530.033*
C440.2412 (2)0.44471 (17)0.58575 (12)0.0215 (5)
H440.27450.45760.62380.026*
C450.6032 (2)0.10402 (16)0.65769 (10)0.0141 (4)
C460.5259 (2)0.02773 (16)0.67787 (10)0.0150 (4)
H460.42550.04140.68130.018*
C470.5958 (2)0.06828 (17)0.69293 (11)0.0180 (5)
H470.54330.12020.70740.022*
C480.7427 (2)0.08827 (17)0.68685 (11)0.0209 (5)
H480.79030.1540.6970.025*
C490.8201 (2)0.01322 (17)0.66622 (11)0.0203 (5)
H490.92040.02750.66180.024*
C500.7507 (2)0.08337 (17)0.65195 (11)0.0172 (5)
H500.80380.13520.63830.021*
C510.4775 (2)0.22518 (16)0.55163 (10)0.0145 (4)
C520.4342 (2)0.14306 (17)0.53204 (11)0.0172 (5)
H520.41930.08790.56190.021*
C530.4132 (2)0.14256 (18)0.46862 (11)0.0218 (5)
H530.38240.08730.45530.026*
C540.4369 (2)0.22218 (19)0.42477 (12)0.0245 (5)
H540.4220.22140.38150.029*
C550.4823 (2)0.30330 (19)0.44380 (11)0.0225 (5)
H550.49960.35750.41350.027*
C560.5024 (2)0.30489 (17)0.50684 (11)0.0181 (5)
H560.53330.36040.51980.022*
C570.3692 (2)0.21982 (16)0.74692 (10)0.0137 (4)
C580.3021 (2)0.14614 (16)0.78082 (11)0.0164 (4)
H580.25320.1080.75920.02*
C590.3063 (2)0.12780 (17)0.84639 (11)0.0172 (5)
H590.2580.07820.86910.021*
C600.3801 (2)0.18089 (17)0.87935 (11)0.0182 (5)
C610.4467 (2)0.25418 (17)0.84421 (11)0.0197 (5)
H610.49770.29140.86550.024*
C620.4413 (2)0.27475 (17)0.77930 (11)0.0171 (5)
H620.48650.32610.75680.021*
C630.3924 (3)0.16013 (19)0.95017 (11)0.0247 (5)
H63A0.35120.22120.96940.03*
H63B0.49410.14560.9580.03*
C640.3223 (3)0.0759 (2)0.98406 (12)0.0286 (6)
H64A0.22050.09070.97880.043*
H64B0.33820.06811.02920.043*
H64C0.36280.01450.96610.043*
N10.83303 (17)0.24265 (13)0.17644 (8)0.0141 (4)
N20.35942 (17)0.24277 (13)0.67843 (8)0.0128 (4)
P10.66983 (5)0.26622 (4)0.14637 (3)0.01357 (12)
P20.99377 (5)0.22740 (4)0.13353 (3)0.01236 (12)
P30.19389 (5)0.26192 (4)0.65115 (3)0.01247 (12)
P40.51696 (5)0.22863 (4)0.63272 (3)0.01222 (12)
S10.59676 (6)0.15083 (4)0.12805 (3)0.01966 (13)
S21.10868 (6)0.32748 (4)0.14140 (3)0.01785 (12)
S30.12578 (5)0.14324 (4)0.63558 (3)0.01649 (12)
S40.63275 (6)0.32894 (4)0.63852 (3)0.01812 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0126 (9)0.0130 (11)0.0178 (11)0.0006 (8)0.0011 (8)0.0030 (9)
C20.0136 (9)0.0149 (11)0.0182 (11)0.0002 (8)0.0027 (8)0.0016 (9)
C30.0124 (9)0.0201 (12)0.0205 (12)0.0009 (8)0.0005 (8)0.0017 (9)
C40.0192 (10)0.0180 (12)0.0159 (11)0.0037 (8)0.0011 (8)0.0034 (9)
C50.0210 (11)0.0125 (11)0.0197 (12)0.0007 (8)0.0052 (9)0.0029 (9)
C60.0147 (10)0.0152 (11)0.0213 (12)0.0030 (8)0.0013 (8)0.0023 (9)
C70.0122 (9)0.0148 (11)0.0215 (12)0.0013 (8)0.0004 (8)0.0026 (9)
C80.0166 (10)0.0221 (13)0.0222 (12)0.0021 (9)0.0016 (9)0.0046 (10)
C90.0216 (11)0.0340 (15)0.0202 (12)0.0021 (10)0.0024 (9)0.0003 (11)
C100.0214 (11)0.0270 (14)0.0273 (14)0.0002 (10)0.0029 (10)0.0066 (11)
C110.0214 (11)0.0167 (12)0.0330 (14)0.0052 (9)0.0041 (10)0.0006 (10)
C120.0172 (10)0.0202 (12)0.0230 (12)0.0051 (9)0.0011 (9)0.0036 (10)
C130.0138 (9)0.0150 (11)0.0126 (10)0.0007 (8)0.0004 (8)0.0039 (8)
C140.0125 (9)0.0181 (12)0.0150 (11)0.0016 (8)0.0002 (8)0.0045 (9)
C150.0205 (11)0.0151 (12)0.0175 (11)0.0038 (8)0.0003 (8)0.0030 (9)
C160.0207 (11)0.0175 (12)0.0196 (12)0.0044 (9)0.0023 (9)0.0044 (9)
C170.0131 (10)0.0256 (13)0.0185 (12)0.0024 (9)0.0022 (8)0.0071 (10)
C180.0128 (9)0.0202 (12)0.0159 (11)0.0024 (8)0.0002 (8)0.0059 (9)
C190.0117 (9)0.0181 (12)0.0150 (11)0.0006 (8)0.0011 (8)0.0040 (9)
C200.0162 (10)0.0160 (12)0.0194 (12)0.0014 (8)0.0011 (8)0.0040 (9)
C210.0215 (11)0.0218 (13)0.0215 (12)0.0013 (9)0.0036 (9)0.0081 (10)
C220.0278 (12)0.0303 (15)0.0173 (12)0.0001 (10)0.0025 (9)0.0069 (10)
C230.0241 (11)0.0270 (14)0.0172 (12)0.0048 (10)0.0003 (9)0.0027 (10)
C240.0161 (10)0.0172 (12)0.0203 (12)0.0041 (8)0.0005 (8)0.0022 (9)
C250.0136 (9)0.0171 (11)0.0143 (11)0.0027 (8)0.0018 (8)0.0013 (9)
C260.0204 (11)0.0146 (12)0.0249 (13)0.0016 (9)0.0076 (9)0.0014 (10)
C270.0259 (12)0.0202 (13)0.0268 (14)0.0068 (10)0.0097 (10)0.0063 (11)
C280.0203 (11)0.0355 (15)0.0198 (13)0.0110 (10)0.0020 (9)0.0050 (11)
C290.0208 (11)0.0393 (16)0.0181 (12)0.0034 (10)0.0040 (9)0.0052 (11)
C300.0165 (10)0.0236 (13)0.0189 (12)0.0005 (9)0.0010 (8)0.0025 (10)
C31A0.020 (3)0.038 (4)0.022 (3)0.015 (3)0.005 (2)0.004 (3)
C32A0.034 (3)0.034 (4)0.027 (3)0.001 (2)0.005 (2)0.004 (2)
C32B0.088 (6)0.084 (6)0.021 (3)0.048 (5)0.006 (3)0.002 (3)
C330.0125 (9)0.0105 (10)0.0167 (11)0.0010 (7)0.0007 (8)0.0015 (8)
C340.0144 (10)0.0132 (11)0.0270 (13)0.0024 (8)0.0010 (9)0.0047 (9)
C350.0198 (10)0.0145 (11)0.0205 (12)0.0012 (8)0.0032 (9)0.0042 (9)
C360.0186 (10)0.0170 (12)0.0166 (11)0.0025 (8)0.0009 (8)0.0030 (9)
C370.0123 (9)0.0182 (12)0.0221 (12)0.0005 (8)0.0001 (8)0.0015 (9)
C380.0130 (9)0.0137 (11)0.0176 (11)0.0010 (8)0.0022 (8)0.0024 (9)
C390.0101 (9)0.0139 (11)0.0235 (12)0.0007 (8)0.0015 (8)0.0010 (9)
C400.0143 (10)0.0211 (12)0.0226 (12)0.0013 (8)0.0003 (8)0.0016 (10)
C410.0185 (11)0.0339 (15)0.0250 (13)0.0011 (10)0.0009 (9)0.0025 (11)
C420.0207 (12)0.0289 (15)0.0321 (15)0.0039 (10)0.0060 (10)0.0142 (12)
C430.0208 (11)0.0155 (12)0.0423 (16)0.0027 (9)0.0073 (10)0.0034 (11)
C440.0174 (10)0.0178 (12)0.0284 (13)0.0028 (9)0.0017 (9)0.0014 (10)
C450.0153 (10)0.0147 (11)0.0121 (10)0.0002 (8)0.0002 (8)0.0049 (8)
C460.0132 (9)0.0169 (11)0.0156 (11)0.0009 (8)0.0013 (8)0.0064 (9)
C470.0207 (11)0.0158 (12)0.0177 (11)0.0026 (8)0.0005 (9)0.0042 (9)
C480.0232 (11)0.0159 (12)0.0225 (12)0.0052 (9)0.0060 (9)0.0067 (10)
C490.0139 (10)0.0221 (13)0.0245 (12)0.0029 (8)0.0025 (9)0.0083 (10)
C500.0140 (10)0.0191 (12)0.0192 (11)0.0029 (8)0.0009 (8)0.0046 (9)
C510.0110 (9)0.0158 (11)0.0160 (11)0.0003 (8)0.0013 (8)0.0039 (9)
C520.0162 (10)0.0163 (12)0.0185 (12)0.0018 (8)0.0017 (8)0.0051 (9)
C530.0214 (11)0.0222 (13)0.0227 (13)0.0019 (9)0.0044 (9)0.0110 (10)
C540.0222 (11)0.0331 (15)0.0166 (12)0.0031 (10)0.0028 (9)0.0063 (11)
C550.0191 (11)0.0278 (14)0.0179 (12)0.0007 (9)0.0015 (9)0.0014 (10)
C560.0141 (10)0.0194 (12)0.0196 (12)0.0017 (8)0.0011 (8)0.0012 (9)
C570.0121 (9)0.0132 (11)0.0153 (11)0.0001 (8)0.0001 (8)0.0032 (8)
C580.0144 (10)0.0157 (11)0.0199 (12)0.0020 (8)0.0003 (8)0.0055 (9)
C590.0169 (10)0.0152 (11)0.0184 (11)0.0021 (8)0.0015 (8)0.0011 (9)
C600.0174 (10)0.0194 (12)0.0165 (11)0.0019 (8)0.0002 (8)0.0040 (9)
C610.0196 (10)0.0209 (12)0.0204 (12)0.0051 (9)0.0012 (9)0.0073 (10)
C620.0157 (10)0.0158 (11)0.0208 (12)0.0053 (8)0.0002 (8)0.0032 (9)
C630.0323 (13)0.0279 (14)0.0137 (11)0.0035 (10)0.0032 (9)0.0034 (10)
C640.0338 (14)0.0337 (15)0.0160 (12)0.0034 (11)0.0017 (10)0.0001 (11)
N10.0125 (8)0.0149 (9)0.0145 (9)0.0013 (7)0.0010 (7)0.0025 (7)
N20.0112 (8)0.0132 (9)0.0142 (9)0.0024 (6)0.0009 (6)0.0034 (7)
P10.0114 (2)0.0116 (3)0.0184 (3)0.00273 (19)0.0005 (2)0.0043 (2)
P20.0112 (2)0.0123 (3)0.0142 (3)0.00285 (19)0.00019 (19)0.0034 (2)
P30.0108 (2)0.0107 (3)0.0163 (3)0.00226 (19)0.00034 (19)0.0027 (2)
P40.0110 (2)0.0121 (3)0.0142 (3)0.00277 (19)0.00019 (19)0.0036 (2)
S10.0173 (3)0.0155 (3)0.0286 (3)0.0069 (2)0.0029 (2)0.0094 (2)
S20.0171 (2)0.0173 (3)0.0216 (3)0.0079 (2)0.0007 (2)0.0064 (2)
S30.0162 (2)0.0135 (3)0.0214 (3)0.0049 (2)0.0010 (2)0.0049 (2)
S40.0168 (2)0.0176 (3)0.0225 (3)0.0085 (2)0.0021 (2)0.0066 (2)
Geometric parameters (Å, º) top
C1—C21.393 (3)C33—C341.400 (3)
C1—C61.402 (3)C33—P31.818 (2)
C1—P11.819 (2)C34—C351.390 (3)
C2—C31.390 (3)C34—H340.95
C2—H20.95C35—C361.384 (3)
C3—C41.381 (3)C35—H350.95
C3—H30.95C36—C371.387 (3)
C4—C51.389 (3)C36—H360.95
C4—H40.95C37—C381.391 (3)
C5—C61.386 (3)C37—H370.95
C5—H50.95C38—H380.95
C6—H60.95C39—C401.395 (3)
C7—C81.396 (3)C39—C441.400 (3)
C7—C121.398 (3)C39—P31.813 (2)
C7—P11.813 (2)C40—C411.388 (3)
C8—C91.392 (3)C40—H400.95
C8—H80.95C41—C421.383 (4)
C9—C101.382 (4)C41—H410.95
C9—H90.95C42—C431.381 (4)
C10—C111.389 (4)C42—H420.95
C10—H100.95C43—C441.389 (3)
C11—C121.391 (3)C43—H430.95
C11—H110.95C44—H440.95
C12—H120.95C45—C461.394 (3)
C13—C141.397 (3)C45—C501.397 (3)
C13—C181.398 (3)C45—P41.811 (2)
C13—P21.806 (2)C46—C471.390 (3)
C14—C151.387 (3)C46—H460.95
C14—H140.95C47—C481.391 (3)
C15—C161.391 (3)C47—H470.95
C15—H150.95C48—C491.382 (3)
C16—C171.386 (3)C48—H480.95
C16—H160.95C49—C501.392 (3)
C17—C181.386 (3)C49—H490.95
C17—H170.95C50—H500.95
C18—H180.95C51—C521.398 (3)
C19—C241.396 (3)C51—C561.399 (3)
C19—C201.398 (3)C51—P41.816 (2)
C19—P21.814 (2)C52—C531.389 (3)
C20—C211.390 (3)C52—H520.95
C20—H200.95C53—C541.384 (4)
C21—C221.386 (3)C53—H530.95
C21—H210.95C54—C551.391 (4)
C22—C231.388 (4)C54—H540.95
C22—H220.95C55—C561.382 (3)
C23—C241.386 (3)C55—H550.95
C23—H230.95C56—H560.95
C24—H240.95C57—C581.387 (3)
C25—C261.392 (3)C57—C621.395 (3)
C25—C301.394 (3)C57—N21.464 (3)
C25—N11.461 (3)C58—C591.393 (3)
C26—C271.386 (3)C58—H580.95
C26—H260.95C59—C601.396 (3)
C27—C281.400 (4)C59—H590.95
C27—H270.95C60—C611.391 (3)
C28—C291.385 (4)C60—C631.514 (3)
C28—C31A1.491 (6)C61—C621.382 (3)
C28—C31B1.565 (7)C61—H610.95
C29—C301.389 (3)C62—H620.95
C29—H290.95C63—C641.514 (4)
C30—H300.95C63—H63A0.99
C31A—C32A1.527 (2)C63—H63B0.99
C31A—H31A0.99C64—H64A0.98
C31A—H31B0.99C64—H64B0.98
C32A—H32A0.98C64—H64C0.98
C32A—H32B0.98N1—P11.7160 (17)
C32A—H32C0.98N1—P21.7183 (18)
C32B—C31B1.455 (8)N2—P31.7138 (17)
C32B—H32D0.98N2—P41.7214 (17)
C32B—H32E0.98P1—S11.9467 (8)
C32B—H32F0.98P2—S21.9466 (8)
C31B—H31C0.99P3—S31.9446 (8)
C31B—H31D0.99P4—S41.9451 (8)
C33—C381.394 (3)
C2—C1—C6119.05 (19)C37—C36—H36120.1
C2—C1—P1118.31 (17)C36—C37—C38120.2 (2)
C6—C1—P1122.58 (16)C36—C37—H37119.9
C3—C2—C1120.4 (2)C38—C37—H37119.9
C3—C2—H2119.8C37—C38—C33120.3 (2)
C1—C2—H2119.8C37—C38—H38119.9
C4—C3—C2120.2 (2)C33—C38—H38119.9
C4—C3—H3119.9C40—C39—C44119.4 (2)
C2—C3—H3119.9C40—C39—P3119.23 (18)
C3—C4—C5120.0 (2)C44—C39—P3121.27 (18)
C3—C4—H4120C41—C40—C39120.0 (2)
C5—C4—H4120C41—C40—H40120
C6—C5—C4120.3 (2)C39—C40—H40120
C6—C5—H5119.9C42—C41—C40120.3 (2)
C4—C5—H5119.9C42—C41—H41119.8
C5—C6—C1120.1 (2)C40—C41—H41119.8
C5—C6—H6119.9C43—C42—C41120.1 (2)
C1—C6—H6119.9C43—C42—H42120
C8—C7—C12119.5 (2)C41—C42—H42120
C8—C7—P1119.45 (18)C42—C43—C44120.4 (2)
C12—C7—P1121.05 (17)C42—C43—H43119.8
C9—C8—C7119.7 (2)C44—C43—H43119.8
C9—C8—H8120.1C43—C44—C39119.8 (2)
C7—C8—H8120.1C43—C44—H44120.1
C10—C9—C8120.8 (2)C39—C44—H44120.1
C10—C9—H9119.6C46—C45—C50119.8 (2)
C8—C9—H9119.6C46—C45—P4121.54 (15)
C9—C10—C11119.7 (2)C50—C45—P4118.51 (17)
C9—C10—H10120.2C47—C46—C45119.97 (19)
C11—C10—H10120.2C47—C46—H46120
C10—C11—C12120.2 (2)C45—C46—H46120
C10—C11—H11119.9C46—C47—C48119.9 (2)
C12—C11—H11119.9C46—C47—H47120.1
C11—C12—C7120.1 (2)C48—C47—H47120.1
C11—C12—H12119.9C49—C48—C47120.5 (2)
C7—C12—H12119.9C49—C48—H48119.8
C14—C13—C18119.6 (2)C47—C48—H48119.8
C14—C13—P2121.53 (15)C48—C49—C50119.9 (2)
C18—C13—P2118.75 (17)C48—C49—H49120.1
C15—C14—C13120.00 (19)C50—C49—H49120.1
C15—C14—H14120C49—C50—C45120.0 (2)
C13—C14—H14120C49—C50—H50120
C14—C15—C16120.0 (2)C45—C50—H50120
C14—C15—H15120C52—C51—C56119.5 (2)
C16—C15—H15120C52—C51—P4122.32 (17)
C17—C16—C15120.2 (2)C56—C51—P4117.95 (17)
C17—C16—H16119.9C53—C52—C51119.7 (2)
C15—C16—H16119.9C53—C52—H52120.2
C16—C17—C18120.0 (2)C51—C52—H52120.2
C16—C17—H17120C54—C53—C52120.3 (2)
C18—C17—H17120C54—C53—H53119.8
C17—C18—C13120.1 (2)C52—C53—H53119.8
C17—C18—H18119.9C53—C54—C55120.2 (2)
C13—C18—H18119.9C53—C54—H54119.9
C24—C19—C20119.7 (2)C55—C54—H54119.9
C24—C19—P2117.55 (17)C56—C55—C54119.9 (2)
C20—C19—P2122.52 (17)C56—C55—H55120.1
C21—C20—C19119.9 (2)C54—C55—H55120.1
C21—C20—H20120.1C55—C56—C51120.3 (2)
C19—C20—H20120.1C55—C56—H56119.8
C22—C21—C20120.1 (2)C51—C56—H56119.8
C22—C21—H21120C58—C57—C62119.1 (2)
C20—C21—H21120C58—C57—N2120.59 (19)
C21—C22—C23120.2 (2)C62—C57—N2120.23 (19)
C21—C22—H22119.9C57—C58—C59120.3 (2)
C23—C22—H22119.9C57—C58—H58119.8
C24—C23—C22120.1 (2)C59—C58—H58119.8
C24—C23—H23119.9C58—C59—C60121.3 (2)
C22—C23—H23119.9C58—C59—H59119.4
C23—C24—C19120.0 (2)C60—C59—H59119.4
C23—C24—H24120C61—C60—C59117.3 (2)
C19—C24—H24120C61—C60—C63119.9 (2)
C26—C25—C30119.0 (2)C59—C60—C63122.9 (2)
C26—C25—N1120.7 (2)C62—C61—C60122.2 (2)
C30—C25—N1120.3 (2)C62—C61—H61118.9
C27—C26—C25120.3 (2)C60—C61—H61118.9
C27—C26—H26119.9C61—C62—C57119.8 (2)
C25—C26—H26119.9C61—C62—H62120.1
C26—C27—C28121.5 (2)C57—C62—H62120.1
C26—C27—H27119.2C60—C63—C64116.2 (2)
C28—C27—H27119.2C60—C63—H63A108.2
C29—C28—C27117.2 (2)C64—C63—H63A108.2
C29—C28—C31A134.5 (3)C60—C63—H63B108.2
C27—C28—C31A108.2 (3)C64—C63—H63B108.2
C29—C28—C31B115.3 (3)H63A—C63—H63B107.4
C27—C28—C31B127.5 (3)C63—C64—H64A109.5
C28—C29—C30122.2 (2)C63—C64—H64B109.5
C28—C29—H29118.9H64A—C64—H64B109.5
C30—C29—H29118.9C63—C64—H64C109.5
C29—C30—C25119.8 (2)H64A—C64—H64C109.5
C29—C30—H30120.1H64B—C64—H64C109.5
C25—C30—H30120.1C25—N1—P1116.96 (13)
C28—C31A—C32A105.0 (4)C25—N1—P2116.05 (13)
C28—C31A—H31A110.8P1—N1—P2126.34 (11)
C32A—C31A—H31A110.8C57—N2—P3117.07 (13)
C28—C31A—H31B110.8C57—N2—P4116.11 (13)
C32A—C31A—H31B110.8P3—N2—P4125.98 (11)
H31A—C31A—H31B108.8N1—P1—C7105.68 (9)
C31B—C32B—H32D109.5N1—P1—C1102.94 (9)
C31B—C32B—H32E109.5C7—P1—C1105.08 (10)
H32D—C32B—H32E109.5N1—P1—S1115.77 (7)
C31B—C32B—H32F109.5C7—P1—S1113.74 (8)
H32D—C32B—H32F109.5C1—P1—S1112.50 (8)
H32E—C32B—H32F109.5N1—P2—C13104.68 (9)
C32B—C31B—C28114.5 (5)N1—P2—C19108.30 (9)
C32B—C31B—H31C108.6C13—P2—C19104.31 (10)
C28—C31B—H31C108.6N1—P2—S2113.97 (7)
C32B—C31B—H31D108.6C13—P2—S2113.18 (7)
C28—C31B—H31D108.6C19—P2—S2111.69 (8)
H31C—C31B—H31D107.6N2—P3—C39106.08 (9)
C38—C33—C34119.26 (19)N2—P3—C33103.69 (9)
C38—C33—P3117.85 (16)C39—P3—C33103.83 (10)
C34—C33—P3122.70 (16)N2—P3—S3115.40 (7)
C35—C34—C33120.0 (2)C39—P3—S3113.83 (8)
C35—C34—H34120C33—P3—S3112.84 (8)
C33—C34—H34120N2—P4—C45104.84 (9)
C36—C35—C34120.4 (2)N2—P4—C51107.95 (9)
C36—C35—H35119.8C45—P4—C51104.40 (10)
C34—C35—H35119.8N2—P4—S4114.04 (7)
C35—C36—C37119.9 (2)C45—P4—S4113.23 (7)
C35—C36—H36120.1C51—P4—S4111.68 (8)
C6—C1—C2—C30.5 (3)C59—C60—C61—C620.0 (3)
P1—C1—C2—C3177.76 (16)C63—C60—C61—C62178.6 (2)
C1—C2—C3—C40.1 (3)C60—C61—C62—C571.2 (3)
C2—C3—C4—C50.4 (3)C58—C57—C62—C611.0 (3)
C3—C4—C5—C60.0 (3)N2—C57—C62—C61178.31 (18)
C4—C5—C6—C10.6 (3)C61—C60—C63—C64177.2 (2)
C2—C1—C6—C50.9 (3)C59—C60—C63—C641.3 (3)
P1—C1—C6—C5177.99 (17)C26—C25—N1—P151.1 (2)
C12—C7—C8—C90.7 (3)C30—C25—N1—P1126.23 (18)
P1—C7—C8—C9178.32 (17)C26—C25—N1—P2120.22 (19)
C7—C8—C9—C101.0 (3)C30—C25—N1—P262.5 (2)
C8—C9—C10—C110.3 (4)C58—C57—N2—P350.0 (2)
C9—C10—C11—C120.5 (4)C62—C57—N2—P3127.31 (18)
C10—C11—C12—C70.7 (3)C58—C57—N2—P4120.15 (18)
C8—C7—C12—C110.1 (3)C62—C57—N2—P462.5 (2)
P1—C7—C12—C11177.45 (17)C25—N1—P1—C7146.52 (16)
C18—C13—C14—C151.6 (3)P2—N1—P1—C743.21 (16)
P2—C13—C14—C15176.79 (17)C25—N1—P1—C136.54 (18)
C13—C14—C15—C162.2 (3)P2—N1—P1—C1153.19 (13)
C14—C15—C16—C171.0 (3)C25—N1—P1—S186.61 (16)
C15—C16—C17—C180.7 (3)P2—N1—P1—S183.65 (13)
C16—C17—C18—C131.3 (3)C8—C7—P1—N1130.08 (17)
C14—C13—C18—C170.1 (3)C12—C7—P1—N152.36 (19)
P2—C13—C18—C17175.20 (17)C8—C7—P1—C1121.48 (18)
C24—C19—C20—C211.3 (3)C12—C7—P1—C156.09 (19)
P2—C19—C20—C21175.59 (16)C8—C7—P1—S12.00 (19)
C19—C20—C21—C220.8 (3)C12—C7—P1—S1179.56 (15)
C20—C21—C22—C230.4 (3)C2—C1—P1—N1142.13 (17)
C21—C22—C23—C241.0 (3)C6—C1—P1—N140.7 (2)
C22—C23—C24—C190.5 (3)C2—C1—P1—C7107.43 (18)
C20—C19—C24—C230.7 (3)C6—C1—P1—C769.7 (2)
P2—C19—C24—C23175.22 (17)C2—C1—P1—S116.83 (19)
C30—C25—C26—C270.4 (3)C6—C1—P1—S1166.03 (16)
N1—C25—C26—C27176.92 (19)C25—N1—P2—C1351.34 (17)
C25—C26—C27—C281.3 (3)P1—N1—P2—C13119.00 (14)
C26—C27—C28—C291.1 (3)C25—N1—P2—C19162.19 (16)
C26—C27—C28—C31A176.5 (3)P1—N1—P2—C198.16 (17)
C26—C27—C28—C31B179.7 (3)C25—N1—P2—S272.84 (16)
C27—C28—C29—C300.0 (3)P1—N1—P2—S2116.82 (12)
C31A—C28—C29—C30176.8 (4)C14—C13—P2—N133.0 (2)
C31B—C28—C29—C30179.3 (3)C18—C13—P2—N1151.82 (17)
C28—C29—C30—C250.9 (3)C14—C13—P2—C1980.73 (19)
C26—C25—C30—C290.7 (3)C18—C13—P2—C1994.49 (18)
N1—C25—C30—C29178.00 (19)C14—C13—P2—S2157.65 (16)
C29—C28—C31A—C32A7.0 (6)C18—C13—P2—S227.13 (19)
C27—C28—C31A—C32A169.9 (3)C24—C19—P2—N1115.33 (17)
C31B—C28—C31A—C32A17.6 (8)C20—C19—P2—N170.27 (19)
C29—C28—C31B—C32B94.2 (6)C24—C19—P2—C13133.58 (17)
C27—C28—C31B—C32B86.6 (7)C20—C19—P2—C1340.82 (19)
C31A—C28—C31B—C32B77.5 (10)C24—C19—P2—S210.98 (18)
C38—C33—C34—C351.0 (3)C20—C19—P2—S2163.42 (15)
P3—C33—C34—C35175.95 (17)C57—N2—P3—C39146.55 (16)
C33—C34—C35—C360.6 (3)P4—N2—P3—C3944.39 (15)
C34—C35—C36—C370.2 (3)C57—N2—P3—C3337.51 (17)
C35—C36—C37—C380.6 (3)P4—N2—P3—C33153.44 (13)
C36—C37—C38—C330.2 (3)C57—N2—P3—S386.40 (15)
C34—C33—C38—C370.5 (3)P4—N2—P3—S382.65 (13)
P3—C33—C38—C37175.77 (16)C40—C39—P3—N2130.71 (17)
C44—C39—C40—C411.2 (3)C44—C39—P3—N252.92 (19)
P3—C39—C40—C41177.63 (17)C40—C39—P3—C33120.34 (17)
C39—C40—C41—C420.9 (3)C44—C39—P3—C3356.03 (19)
C40—C41—C42—C430.1 (4)C40—C39—P3—S32.73 (19)
C41—C42—C43—C440.3 (4)C44—C39—P3—S3179.10 (15)
C42—C43—C44—C390.1 (3)C38—C33—P3—N2146.72 (16)
C40—C39—C44—C430.8 (3)C34—C33—P3—N238.2 (2)
P3—C39—C44—C43177.17 (17)C38—C33—P3—C39102.57 (18)
C50—C45—C46—C470.8 (3)C34—C33—P3—C3972.49 (19)
P4—C45—C46—C47175.98 (17)C38—C33—P3—S321.15 (19)
C45—C46—C47—C481.0 (3)C34—C33—P3—S3163.79 (16)
C46—C47—C48—C490.3 (3)C57—N2—P4—C4552.68 (17)
C47—C48—C49—C500.6 (4)P3—N2—P4—C45116.47 (13)
C48—C49—C50—C450.8 (3)C57—N2—P4—C51163.55 (15)
C46—C45—C50—C490.2 (3)P3—N2—P4—C515.60 (16)
P4—C45—C50—C49175.19 (17)C57—N2—P4—S471.72 (16)
C56—C51—C52—C531.6 (3)P3—N2—P4—S4119.13 (11)
P4—C51—C52—C53176.41 (16)C46—C45—P4—N232.5 (2)
C51—C52—C53—C541.0 (3)C50—C45—P4—N2152.18 (17)
C52—C53—C54—C550.2 (3)C46—C45—P4—C5180.85 (19)
C53—C54—C55—C560.7 (3)C50—C45—P4—C5194.42 (18)
C54—C55—C56—C510.1 (3)C46—C45—P4—S4157.47 (16)
C52—C51—C56—C551.0 (3)C50—C45—P4—S427.3 (2)
P4—C51—C56—C55176.08 (16)C52—C51—P4—N273.50 (18)
C62—C57—C58—C590.3 (3)C56—C51—P4—N2111.58 (17)
N2—C57—C58—C59176.99 (18)C52—C51—P4—C4537.67 (19)
C57—C58—C59—C601.5 (3)C56—C51—P4—C45137.25 (16)
C58—C59—C60—C611.3 (3)C52—C51—P4—S4160.37 (15)
C58—C59—C60—C63177.3 (2)C56—C51—P4—S414.55 (18)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C19–C24 and C57–C62 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17—H17···Cg2i0.952.973.759 (3)141
C64—H64A···Cg1ii0.982.883.767 (3)151
Symmetry codes: (i) x+2, y, z+1; (ii) x1, y, z+1.

Experimental details

Crystal data
Chemical formulaC32H29NP2S2
Mr553.62
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.6305 (11), 13.8027 (14), 21.360 (2)
α, β, γ (°)82.484 (2), 84.635 (2), 79.975 (2)
V3)2764.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.17 × 0.08 × 0.08
Data collection
DiffractometerBruker X8 APEXII 4K KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.946, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
56725, 13522, 9271
Rint0.054
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.107, 1.00
No. of reflections13522
No. of parameters684
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 0.36

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SAINT-Plus and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C19–C24 and C57–C62 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17—H17···Cg2i0.952.973.759 (3)141
C64—H64A···Cg1ii0.982.883.767 (3)151
Symmetry codes: (i) x+2, y, z+1; (ii) x1, y, z+1.
 

Acknowledgements

The authors gratefully acknowledge the financial support of GMRDC, University of Fort Hare, South Africa.

References

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Volume 68| Part 12| December 2012| Pages o3491-o3492
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