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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 5| May 2011| Pages o1212-o1213

The Phospha–Michael addition product {(t-BuNH)P(μ-N-t-Bu)2P(=N-t-Bu)—C(=CH2)CH(p-CH3O—C6H4)-P(O)[(OCH2C(CH3)2CH2O)]}

aSchool of Chemistry, University of Hyderabad, Hyderabad 500 046, India
*Correspondence e-mail: venu.srinivas@gmail.com

(Received 4 February 2011; accepted 14 April 2011; online 29 April 2011)

The title compound, 2-{2-[1,3-di-tert-butyl-4-(tert-butyl­amino)-2-(tert-butyl­imino)-1,3,2λ5,4-diaza­diphosphetidin-2-yl]-1-(4-meth­oxy­phen­yl)prop-2-en-1-yl}-5,5-dimethyl-1,3,2λ5-dioxaphosphinan-2-one, C31H57N4O4P3, was synthesized from the Phospha–Michael addition reaction of cyclo­diphos­pha­zane [(t-BuNH)P(μ-Nt-Bu)]2 and allenyl­phospho­nate [(OCH2C(CH3)2CH2O)P(O)C(p-CH3O—C6H4)=C=CH2]. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules. The structure exhibits pseudosymmetry but attempts to solve it in a higher (monoclinic) space group were unsuccessful.

Related literature

For background to cyclo­diphosph(III)aza­nes, see: Rama Suresh et al. (2009[Rama Suresh, R. & Kumara Swamy, K. C. (2009). Tetrahedron Lett. 50, 6004-6007.]); Balakrishna (2010[Balakrishna, M. S. (2010). J. Organomet. Chem. 695, 925-936.]); Balakrishna et al. (2010[Balakrishna, M. S., Venkateswaran, R. & Mague, J. T. (2010). Dalton Trans. pp. 11149-11162.]). For their use as probes for organic reactions (the P atom reacts readily with activated alkenes/alkynes or azodicarboxyl­ates), see: Satish Kumar et al. (2004[Satish Kumar, N., Praveen Kumar, K., Pavan Kumar, K. V. P., Kommana, P., Vittal, J. J. & Kumara Swamy, K. C. (2004). J. Org. Chem. 69, 1880-1889.]); Praveen Kumar et al. (2004[Praveen Kumar, K., Chakravarty, M. & Kumara Swamy, K. C. (2004). Z. Anorg. Allg. Chem. 630, 2063-2070.]); Balaraman & Kumara Swamy (2004[Balaraman, E. & Kumara Swamy, K. C. (2004). Synthesis, pp. 3037-3042.]); Bhuvan Kumar & Kumara Swamy (2007[Bhuvan Kumar, N. N. & Kumara Swamy, K. C. (2007). Polyhedron, 26, 883-890.], 2008[Bhuvan Kumar, N. N. & Kumara Swamy, K. C. (2008). Tetrahedron Lett. 49, 7135-7138.]); Kumara Swamy et al. (2010[Kumara Swamy, K. C., Gangadhararao, G., Rama Suresh, R., Bhuvan Kumar, N. N. & Chakravarty, M. (2010). J. Organomet. Chem. 695, 1042-1051.], 2011[Kumara Swamy, K. C., Gangadhararao, G., Srinivas, V., Bhuvan Kumar, N. N., Balaraman, E. & Chakravarty, M. (2011). Inorg. Chim. Acta. In the press. doi:10.1016/j.ica.2010.12.072. ]). It has been shown recently that their reactions with allenes generates a chiral carbon center and in some cases spontaneous resolution by crystallization can be effected (Bhuvan Kumar & Kumara Swamy (2008[Bhuvan Kumar, N. N. & Kumara Swamy, K. C. (2008). Tetrahedron Lett. 49, 7135-7138.]). For related structures, see: Chakravarty et al. (2005[Chakravarty, M., Kommana, P. & Kumara Swamy, K. C. (2005). Chem. Commun. pp. 5396-5398.]); Kumara Swamy et al. (2010[Kumara Swamy, K. C., Gangadhararao, G., Rama Suresh, R., Bhuvan Kumar, N. N. & Chakravarty, M. (2010). J. Organomet. Chem. 695, 1042-1051.], 2011[Kumara Swamy, K. C., Gangadhararao, G., Srinivas, V., Bhuvan Kumar, N. N., Balaraman, E. & Chakravarty, M. (2011). Inorg. Chim. Acta. In the press. doi:10.1016/j.ica.2010.12.072. ]).

[Scheme 1]

Experimental

Crystal data
  • C31H57N4O4P3

  • Mr = 642.72

  • Triclinic, [P \overline 1]

  • a = 13.8603 (9) Å

  • b = 15.7746 (10) Å

  • c = 16.2606 (11) Å

  • α = 88.004 (1)°

  • β = 84.949 (1)°

  • γ = 87.600 (1)°

  • V = 3536.6 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 100 K

  • 0.22 × 0.18 × 0.14 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.956, Tmax = 0.972

  • 27730 measured reflections

  • 12397 independent reflections

  • 9894 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.128

  • S = 1.01

  • 12397 reflections

  • 795 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N8—H8D⋯O1i 0.82 (2) 2.61 (3) 3.394 (2) 160 (2)
N4—H4D⋯O5ii 0.84 (3) 2.58 (3) 3.378 (2) 158 (2)
C26—H26B⋯O5iii 0.96 2.49 3.325 (3) 145
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Cyclodiphosph(III)azanes are good phosphorus based ligands (Rama Suresh et al., 2009; Balakrishna et al., 2010). They can also act as probes for organic reactions since the P(III) centre reacts readily with activated alkenes/ alkynes or azodicarboxylates (Satish Kumar et al., 2004; Praveen Kumar et al., 2004; Balaraman et al., 2004; Bhuvan Kumar et al., 2007; 2008; Kumara Swamy et al., 2010; 2011). It has been shown recently that their reactions with allenes generates a chiral carbon center and in some cases spontaneous resolution by crystallization can be effected (Bhuvan Kumar et al., 2008). To probe this aspect further we reacted cyclodiphosph(III)azane [(t-BuNH)P(µ-N-t-Bu)]2 (1a) with allene (OCH2CMe2CH2O)P(O)C(C6H4-p-OCH3)CCH2 (1b). The reaction afforded compound 1 (Scheme 1) as essentially a single product. The X-ray structure of compound 1 [Figure 1] clearly show the phosphinimine moiety at P(2) and P(5) with P—N distances of 1.546 (4) and 1.546 (1) that are slightly longer than the structures reported earlier (Chakravarty et al., 2005; Kumara Swamy et al., 2010). However, these are still in the range expected for P=N distances; the P—N single bond distances in the cyclophosphazane ring also lie in the same range of the previously reported structures (Kumara Swamy et al., 2011). However, the P—N(ring) distances involving P(III) phosphorus atoms are comparatively longer than that for P(V) phosphorus. The P–C distances are also in line with the structures as written. The P—N—P and N—P—N bond angles are also in the expected range.The crystal packing in compound 1 is mostly governed by classical hydrogen bonds. The two molecules in the asymmetric unit are extended in a one-dimensional fashion through N—H···O interactions [N(4)—H(4D)···O5 and N(8)—H(8D)···O(1)] (Figure 2). But only the first molecule was also having C—H···O(=P) [C26—H(26B)···O(5)] interactions by OCH3 hydrogen and with the phosphoryl oxygen (PO) of the second molecule. The crystal structure is showing an alert due to the psuedo symmetry. We have investigated the possibility of solving in higher symmetry space group and also the presence of pseudo-centre of symmetry. All our attempts to solve the structure in a higher symmetry (in Monoclinic) space group were not successful. Therefore, we strongly believe that there is only a pseudo-symmetry.

Related literature top

For background to cyclodiphosph(III)azanes, see: Rama Suresh et al. (2009); Balakrishna (2010); Balakrishna et al. (2010). For their use as as probes for organic reactions (the P atom reacts readily with activated alkenes/alkynes or azodicarboxylates), see: Satish Kumar et al. (2004); Praveen Kumar et al. (2004); Balaraman & Kumara Swamy (2004); Bhuvan Kumar & Kumara Swamy (2007, 2008); Kumara Swamy et al. (2010, 2011). It has been shown recently that their reactions with allenes generates a chiral carbon center and in some cases spontaneous resolution by crystallization can be effected (Bhuvan Kumar & Kumara Swamy (2008). For related structures, see: Chakravarty et al. (2005); Kumara Swamy et al. (2010, 2011). For related literature [on what subject?], see: Bhuvan Kumar et al. (2006); Stahl (2000); Vijjulatha, Kumara Swamy et al. (1999); Vijjulatha, Kumaraswamy et al. (1999).

Experimental top

Comopound 1: This compound (1) was obtained by the reaction of cyclodiphosphazane 1a (0.561 g, 1.61 mmol) and allenylphosphonate 1b (0 474 g, 1.61 mmol) in dry toluene (8 ml) for 20 h. The solution (toluene) was concentrated in vacuo (to ca 3 ml) and cooled for 1 day at -4°C to obtain the colorless crystals of product. Yield: 0.956 g (92%). mp: 150–154°C. IR (KBr, cm-1): 3337, 2967, 2897, 1615, 1584, 1510, 1464, 1364, 1281, 1209, 1063, 1028, 885. 1H NMR (400 MHz, CDCl3): δ 0.83, 1.08, 1.18, 1.29 and 1.37 (5 s, 42H, C(CH3)2+C(CH3)3), 2.69 (d, 2J(P—H) = 7.6 Hz, 1H, NH), 3.78 (s, 3H, Ar—OCH3) 3.82–4.36 (m, 4H, OCH2), 5.76 (d, 3J(P—H) = 28.8 Hz, 1H, =CHAHB cis to P), 6.00 (dd, 3J(P—H) = 15.2 Hz, 2J(P—H) = 18.0 Hz, 1H, P(O)CH), 6.76 (d, 3J(P—H) = 52.4 Hz, 1H, =CHAHB trans to P), 6.81 (d, 3J(H—H) = 8.4 Hz, 2H, Ar-H), 7.47 (d, 3J(H—H) = 8.0 Hz, 2H, Ar-H). 13C NMR (100 MHz, CDCl3): δ 20.81 and 21.85 (2 s, C(CH3)2), 31.10 (d, 3J(P—C) = 23.4 Hz, C(CH3)3), 32.31 (d, 3J(P—C) = 6.0 Hz, C(CH3)3), 32.78 (d, 3J(P—C) = 9.2 Hz, C(CH3)3), 34.39 (d, 3J(P—C) = 11.2 Hz, C(CH3)3), 40.72 (d, 1J(P—C) = 125.4 Hz, P(O)C(Ar)), 51.31 (d, 2J(P—C) = 14.5 Hz, C(CH3)3), 52.25 (d, 2J(P—C) = 8.8 Hz, C(CH3)3), 52.51 (d, 2J(P—C) = 7.7 Hz, C(CH3)3), 55.08 (Ar—OCH3),76.38 and 76.42 (2 s, OCH2), 113.52, 128.06, 131.05, 131.12, 158.67 (d, 2J(P—C) = 6.4 Hz, Ar-C + PC=CH2), 143.56 (d, 1J(P—C) = 159.0 Hz, PC=CH2). 31P NMR (160 MHz, CDCl3): δ -18.90 (dd, 3J(P—P) = 35.8 Hz, 2J(P—P) = 6.7 Hz), 20.91 (d, 3J(P—P) = 35.8 Hz), 70.99 (br d, 2J(P—P) = 6.7 Hz). LC—MS: m/z 643 [M+1]+. Anal. Calc. For C31H57N4O4P3: C, 57.93; H, 8.94; N, 8.72. Found: C, 57.79; H, 8.98; N, 8.82. A suitable crystal (Shape: blocks: Size: 0.22 x 0.18 x 0.14 mm3) was mounted on a glass fibre and data was collected on BRUKER SMART diffractometer at 100 K.

Refinement top

All H atoms were found on difference maps, with C—H=0.93 Å and included in the final cycles of refinement using a riding model, with Uiso(H)=1.2Ueq(C)

The structure was solved by direct methods and refined by full-matrix least squares methods using standard procedures. Absorption corrections were done using the SADABS program, where applicable. All non-hydrogen atoms were refined anisotropically; hydrogen atoms were fixed by geometry or located by a difference Fourier and refined isotropically.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. An ORTEP representation of compound 1 (Thermal ellipsoids are at 50% probability level). Two molecules are present in the asymmetric unit. Second molecule is not shown for clarity.
[Figure 2] Fig. 2. 1-Dimensional structural unit due to the N—H···O interactions in the crystal structure of compound 1.
2-{2-[1,3-di-tert-butyl-4-(tert-butylamino)-2-(tert-butylimino)- 1,3,2λ5,4-diazadiphosphetidin-2-yl]-1-(4-methoxyphenyl)prop-2-en-1-yl}- 5,5-dimethyl-1,3,2λ5-dioxaphosphinan-2-one top
Crystal data top
C31H57N4O4P3Z = 4
Mr = 642.72F(000) = 1392
Triclinic, P1Dx = 1.207 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.8603 (9) ÅCell parameters from 6427 reflections
b = 15.7746 (10) Åθ = 2.4–26.0°
c = 16.2606 (11) ŵ = 0.21 mm1
α = 88.004 (1)°T = 100 K
β = 84.949 (1)°Blocks, colorless
γ = 87.600 (1)°0.22 × 0.18 × 0.14 mm
V = 3536.6 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
12397 independent reflections
Radiation source: fine-focus sealed tube9894 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.956, Tmax = 0.972k = 1818
27730 measured reflectionsl = 1919
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0649P)2 + 1.2977P]
where P = (Fo2 + 2Fc2)/3
12397 reflections(Δ/σ)max = 0.001
795 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C31H57N4O4P3γ = 87.600 (1)°
Mr = 642.72V = 3536.6 (4) Å3
Triclinic, P1Z = 4
a = 13.8603 (9) ÅMo Kα radiation
b = 15.7746 (10) ŵ = 0.21 mm1
c = 16.2606 (11) ÅT = 100 K
α = 88.004 (1)°0.22 × 0.18 × 0.14 mm
β = 84.949 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
12397 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
9894 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.972Rint = 0.033
27730 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.54 e Å3
12397 reflectionsΔρmin = 0.28 e Å3
795 parameters
Special details top

Experimental. A colorless block with approximate orthogonal dimensions 0.22 x 0.18 x 0.14 mm3 was placed and optically centered on the Bruker SMART CCD system at 100 (2) K.

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*/Ueq
P50.59309 (4)0.74569 (3)0.08104 (3)0.01270 (13)
P60.40564 (4)0.66855 (3)0.27677 (3)0.01388 (13)
P40.66984 (4)0.88814 (3)0.03551 (3)0.01523 (14)
O50.37256 (11)0.74031 (9)0.32774 (9)0.0187 (3)
O80.03668 (11)0.75573 (10)0.05412 (9)0.0233 (4)
O60.33881 (10)0.58979 (9)0.29393 (9)0.0169 (3)
O70.50990 (10)0.63320 (9)0.29590 (9)0.0157 (3)
N60.67820 (12)0.80751 (11)0.11155 (10)0.0148 (4)
C540.12697 (15)0.73681 (13)0.07809 (13)0.0170 (5)
C480.47736 (15)0.76502 (13)0.14219 (12)0.0137 (4)
C550.14671 (15)0.76903 (13)0.15315 (13)0.0168 (5)
H550.09900.80060.18370.020*
N70.60389 (12)0.64798 (11)0.07626 (10)0.0155 (4)
C510.30881 (15)0.70578 (13)0.13897 (12)0.0143 (4)
N80.77127 (13)0.88560 (12)0.02712 (12)0.0186 (4)
C560.23648 (15)0.75457 (13)0.18261 (13)0.0173 (5)
H560.24900.77760.23230.021*
C580.54361 (15)0.55016 (13)0.26565 (13)0.0175 (5)
H58A0.60670.53550.28490.021*
H58B0.55070.55260.20570.021*
C350.45625 (16)0.76226 (15)0.06387 (14)0.0235 (5)
H35A0.48210.70540.05630.035*
H35B0.42170.76590.11260.035*
H35C0.41280.77680.01680.035*
C520.28674 (15)0.67198 (13)0.06574 (13)0.0151 (5)
H520.33320.63770.03670.018*
C360.72204 (16)0.81403 (14)0.19125 (13)0.0187 (5)
C490.45156 (16)0.84466 (13)0.16018 (13)0.0193 (5)
H49A0.39160.85710.18840.023*
H49B0.49340.88810.14460.023*
C570.01704 (17)0.72673 (15)0.02482 (14)0.0245 (5)
H57A0.06150.75110.06680.037*
H57B0.04820.74360.03550.037*
H57C0.02460.66600.02520.037*
C530.19755 (15)0.68757 (13)0.03410 (13)0.0171 (5)
H530.18530.66530.01600.020*
C320.53851 (15)0.82327 (13)0.07322 (13)0.0165 (5)
C400.68215 (16)0.59654 (13)0.03178 (13)0.0176 (5)
C590.47325 (16)0.48183 (13)0.29526 (13)0.0189 (5)
N50.59713 (12)0.81344 (11)0.00120 (10)0.0148 (4)
C500.41072 (15)0.69154 (13)0.16671 (12)0.0140 (4)
H500.43960.64110.13920.017*
C340.49557 (18)0.91388 (14)0.07822 (15)0.0268 (6)
H34A0.45310.92450.02950.040*
H34B0.45970.92090.12610.040*
H34C0.54690.95320.08220.040*
C600.37424 (16)0.50669 (13)0.26594 (14)0.0205 (5)
H60A0.37860.50700.20610.025*
H60B0.32830.46460.28640.025*
C330.60321 (17)0.80532 (15)0.15207 (13)0.0237 (5)
H33A0.65390.84530.15860.036*
H33B0.56520.81070.19870.036*
H33C0.63120.74880.14850.036*
C610.50832 (18)0.39855 (14)0.25481 (15)0.0277 (6)
H61A0.51070.40610.19580.041*
H61B0.46440.35480.27260.041*
H61C0.57190.38260.27060.041*
C440.82293 (16)0.96108 (13)0.06183 (14)0.0189 (5)
C450.78670 (18)0.98684 (15)0.14567 (15)0.0296 (6)
H45A0.79640.93990.18190.044*
H45B0.82211.03410.16920.044*
H45C0.71891.00270.13850.044*
C430.70774 (17)0.52019 (14)0.08743 (14)0.0247 (5)
H43A0.72880.53970.13790.037*
H43B0.75890.48620.05970.037*
H43C0.65170.48670.09960.037*
C370.82582 (18)0.84214 (18)0.17242 (16)0.0358 (7)
H37A0.86160.80180.13750.054*
H37B0.85600.84540.22310.054*
H37C0.82520.89690.14480.054*
C390.72334 (17)0.72728 (14)0.23515 (14)0.0246 (5)
H39A0.65810.70930.24700.037*
H39B0.75340.73080.28590.037*
H39C0.75940.68700.20040.037*
C620.46740 (17)0.47035 (14)0.38906 (13)0.0224 (5)
H62A0.52850.44780.40540.034*
H62B0.41750.43180.40690.034*
H62C0.45260.52420.41380.034*
C410.64407 (17)0.56365 (14)0.04624 (13)0.0225 (5)
H41A0.58570.53390.03150.034*
H41B0.69200.52580.07300.034*
H41C0.63060.61060.08320.034*
C380.6647 (2)0.87766 (16)0.24708 (15)0.0341 (6)
H38A0.65930.93150.21800.051*
H38B0.69760.88430.29580.051*
H38C0.60110.85730.26240.051*
C420.77415 (16)0.64415 (14)0.00713 (14)0.0232 (5)
H42A0.76010.69000.03090.035*
H42B0.82250.60600.01870.035*
H42C0.79780.66640.05540.035*
C470.80763 (18)1.03499 (14)0.00409 (15)0.0288 (6)
H47A0.74021.05220.00150.043*
H47B0.84501.08170.02640.043*
H47C0.82811.01780.04910.043*
C460.93066 (16)0.93594 (15)0.07427 (15)0.0258 (5)
H46A0.95380.91880.02210.039*
H46B0.96590.98350.09730.039*
H46C0.94000.88960.11130.039*
P20.89633 (4)0.24677 (3)0.41973 (3)0.01371 (13)
P10.82093 (4)0.10583 (3)0.47234 (3)0.01574 (14)
P31.09056 (4)0.32194 (3)0.22058 (3)0.01479 (14)
O41.43525 (11)0.25060 (10)0.47038 (9)0.0215 (4)
O20.98715 (10)0.35323 (9)0.19487 (9)0.0164 (3)
O11.13188 (11)0.25206 (9)0.17058 (9)0.0196 (3)
O31.15386 (10)0.40346 (9)0.20836 (9)0.0179 (3)
C231.34641 (15)0.26494 (13)0.44149 (13)0.0164 (5)
C211.18557 (15)0.32641 (13)0.44112 (13)0.0162 (5)
H211.13600.36100.46570.019*
N10.89654 (12)0.18141 (11)0.50433 (10)0.0151 (4)
C251.24771 (15)0.23654 (13)0.33221 (13)0.0167 (5)
H251.24000.20920.28360.020*
C181.02663 (16)0.14940 (13)0.32540 (13)0.0197 (5)
H18A1.08380.13760.29280.024*
H18B0.98350.10660.33940.024*
C171.00657 (15)0.22708 (13)0.35183 (12)0.0143 (4)
N30.88579 (13)0.34459 (11)0.42252 (11)0.0172 (4)
C191.07475 (15)0.30000 (13)0.33072 (12)0.0139 (4)
H191.04260.35080.35530.017*
N20.81034 (12)0.18369 (11)0.39409 (11)0.0157 (4)
C281.01401 (16)0.50577 (13)0.20302 (13)0.0184 (5)
C241.33385 (15)0.22616 (13)0.36802 (13)0.0171 (5)
H241.38420.19280.34280.020*
C201.17163 (15)0.28768 (13)0.36797 (13)0.0148 (4)
C261.45102 (17)0.28712 (14)0.54678 (13)0.0231 (5)
H26A1.44070.34760.54230.035*
H26B1.51630.27390.55960.035*
H26C1.40670.26440.58980.035*
N40.72237 (13)0.11378 (12)0.53761 (11)0.0174 (4)
C290.94605 (16)0.43378 (13)0.22661 (13)0.0182 (5)
H29A0.93480.42890.28630.022*
H29B0.88420.44650.20430.022*
C50.75761 (16)0.17757 (14)0.31903 (14)0.0219 (5)
C271.11183 (16)0.48426 (13)0.23657 (14)0.0204 (5)
H27A1.15610.52870.21920.024*
H27B1.10360.48250.29650.024*
C130.66233 (16)0.04273 (13)0.57061 (14)0.0189 (5)
C40.98429 (18)0.25201 (14)0.60522 (14)0.0261 (5)
H4A1.00540.29220.56240.039*
H4B1.03310.24410.64350.039*
H4C0.92500.27300.63380.039*
C20.92494 (17)0.10746 (15)0.63526 (14)0.0249 (5)
H2A0.86470.13160.65940.037*
H2B0.96950.09900.67700.037*
H2C0.91380.05390.61210.037*
C31.06421 (16)0.12822 (15)0.53081 (14)0.0237 (5)
H3A1.05270.07670.50420.036*
H3B1.10580.11590.57420.036*
H3C1.09470.16740.49120.036*
C70.64933 (17)0.17330 (18)0.34434 (16)0.0352 (6)
H7A0.63750.12380.37930.053*
H7B0.61490.17020.29590.053*
H7C0.62740.22320.37380.053*
C300.97184 (18)0.58638 (14)0.24454 (15)0.0284 (6)
H30A0.90850.59970.22700.043*
H30B1.01330.63260.22930.043*
H30C0.96730.57740.30340.043*
C160.67254 (17)0.03126 (14)0.51240 (14)0.0237 (5)
H16A0.65720.01170.45830.036*
H16B0.62890.07450.53260.036*
H16C0.73790.05420.50950.036*
C90.80892 (16)0.39872 (13)0.46543 (13)0.0195 (5)
C10.96760 (16)0.16767 (13)0.56725 (13)0.0177 (5)
C311.02493 (17)0.51997 (14)0.10952 (13)0.0229 (5)
H31A1.04570.46760.08380.034*
H31B1.07220.56190.09500.034*
H31C0.96380.53930.09080.034*
C140.55715 (16)0.07624 (15)0.57986 (16)0.0283 (6)
H14A0.55100.12210.61740.043*
H14B0.51610.03150.60100.043*
H14C0.53820.09620.52700.043*
C150.69229 (18)0.01271 (15)0.65535 (14)0.0283 (6)
H15A0.75620.01350.64930.042*
H15B0.64730.02760.67960.042*
H15C0.69220.06040.69040.042*
C120.7760 (2)0.46657 (16)0.40394 (16)0.0368 (7)
H12A0.82950.50100.38520.055*
H12B0.72470.50150.43020.055*
H12C0.75290.43990.35760.055*
C60.77596 (19)0.25584 (16)0.26283 (15)0.0331 (6)
H6A0.75560.30600.29240.050*
H6B0.73990.25300.21530.050*
H6C0.84390.25770.24540.050*
C110.8506 (2)0.44271 (16)0.53541 (17)0.0392 (7)
H11A0.86560.40140.57770.059*
H11B0.80390.48410.55820.059*
H11C0.90850.47030.51460.059*
C100.72105 (18)0.35083 (15)0.49979 (17)0.0358 (7)
H10A0.69330.32440.45560.054*
H10B0.67400.38960.52630.054*
H10C0.74020.30810.53930.054*
C80.7922 (2)0.09845 (17)0.27171 (17)0.0404 (7)
H8A0.85810.10450.24940.061*
H8B0.75190.09160.22750.061*
H8C0.78830.04950.30850.061*
C221.27127 (16)0.31485 (13)0.47850 (13)0.0182 (5)
H221.27840.34040.52820.022*
H4D0.7089 (18)0.1594 (17)0.5623 (16)0.032 (7)*
H8D0.7859 (18)0.8433 (16)0.0543 (15)0.026 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P50.0127 (3)0.0133 (3)0.0118 (3)0.0010 (2)0.0003 (2)0.0008 (2)
P60.0142 (3)0.0154 (3)0.0120 (3)0.0005 (2)0.0021 (2)0.0019 (2)
P40.0160 (3)0.0137 (3)0.0158 (3)0.0000 (2)0.0008 (2)0.0016 (2)
O50.0221 (8)0.0195 (8)0.0140 (8)0.0026 (6)0.0009 (6)0.0003 (6)
O80.0168 (8)0.0291 (9)0.0250 (9)0.0032 (7)0.0088 (7)0.0021 (7)
O60.0161 (8)0.0170 (8)0.0171 (8)0.0010 (6)0.0005 (6)0.0034 (6)
O70.0162 (8)0.0151 (8)0.0162 (8)0.0006 (6)0.0040 (6)0.0021 (6)
N60.0150 (9)0.0154 (9)0.0140 (9)0.0006 (7)0.0026 (7)0.0019 (7)
C540.0142 (11)0.0157 (11)0.0216 (12)0.0008 (9)0.0067 (9)0.0056 (9)
C480.0144 (11)0.0163 (11)0.0106 (10)0.0003 (9)0.0031 (9)0.0021 (8)
C550.0170 (11)0.0143 (11)0.0186 (11)0.0015 (9)0.0004 (9)0.0002 (9)
N70.0150 (9)0.0159 (9)0.0149 (9)0.0027 (7)0.0000 (7)0.0002 (7)
C510.0157 (11)0.0124 (10)0.0147 (11)0.0011 (8)0.0017 (9)0.0024 (8)
N80.0208 (10)0.0127 (10)0.0215 (10)0.0016 (8)0.0022 (8)0.0007 (8)
C560.0183 (12)0.0174 (11)0.0163 (11)0.0002 (9)0.0034 (9)0.0009 (9)
C580.0170 (11)0.0166 (11)0.0185 (11)0.0034 (9)0.0023 (9)0.0014 (9)
C350.0223 (13)0.0314 (13)0.0176 (12)0.0053 (10)0.0072 (10)0.0041 (10)
C520.0161 (11)0.0127 (10)0.0161 (11)0.0000 (9)0.0010 (9)0.0003 (8)
C360.0176 (12)0.0229 (12)0.0167 (11)0.0027 (9)0.0058 (9)0.0003 (9)
C490.0176 (12)0.0172 (11)0.0219 (12)0.0003 (9)0.0042 (10)0.0016 (9)
C570.0242 (13)0.0259 (13)0.0254 (13)0.0018 (10)0.0137 (10)0.0034 (10)
C530.0217 (12)0.0165 (11)0.0138 (11)0.0030 (9)0.0047 (9)0.0001 (9)
C320.0180 (11)0.0177 (11)0.0144 (11)0.0013 (9)0.0062 (9)0.0017 (9)
C400.0190 (12)0.0145 (11)0.0186 (11)0.0038 (9)0.0014 (9)0.0014 (9)
C590.0209 (12)0.0165 (11)0.0190 (12)0.0010 (9)0.0017 (10)0.0014 (9)
N50.0155 (9)0.0150 (9)0.0137 (9)0.0004 (7)0.0012 (7)0.0023 (7)
C500.0155 (11)0.0132 (10)0.0129 (10)0.0019 (8)0.0010 (9)0.0011 (8)
C340.0314 (14)0.0239 (13)0.0262 (13)0.0060 (11)0.0131 (11)0.0020 (10)
C600.0228 (12)0.0167 (11)0.0222 (12)0.0023 (9)0.0024 (10)0.0002 (9)
C330.0254 (13)0.0301 (13)0.0157 (12)0.0033 (10)0.0021 (10)0.0006 (10)
C610.0319 (14)0.0208 (12)0.0295 (14)0.0028 (11)0.0000 (11)0.0009 (10)
C440.0197 (12)0.0152 (11)0.0212 (12)0.0033 (9)0.0005 (10)0.0036 (9)
C450.0341 (15)0.0248 (13)0.0300 (14)0.0074 (11)0.0055 (11)0.0116 (11)
C430.0268 (13)0.0214 (12)0.0235 (13)0.0098 (10)0.0044 (10)0.0031 (10)
C370.0285 (14)0.0532 (17)0.0280 (14)0.0183 (13)0.0114 (12)0.0102 (12)
C390.0281 (13)0.0275 (13)0.0192 (12)0.0042 (10)0.0080 (10)0.0042 (10)
C620.0241 (13)0.0230 (12)0.0192 (12)0.0004 (10)0.0014 (10)0.0083 (9)
C410.0273 (13)0.0201 (12)0.0198 (12)0.0034 (10)0.0017 (10)0.0036 (9)
C380.0461 (17)0.0356 (15)0.0225 (13)0.0088 (12)0.0141 (12)0.0109 (11)
C420.0222 (12)0.0216 (12)0.0245 (13)0.0015 (10)0.0052 (10)0.0027 (10)
C470.0368 (15)0.0197 (12)0.0289 (14)0.0062 (11)0.0047 (11)0.0005 (10)
C460.0207 (13)0.0245 (13)0.0317 (14)0.0057 (10)0.0022 (11)0.0020 (10)
P20.0136 (3)0.0131 (3)0.0141 (3)0.0003 (2)0.0009 (2)0.0017 (2)
P10.0163 (3)0.0140 (3)0.0167 (3)0.0004 (2)0.0009 (2)0.0017 (2)
P30.0148 (3)0.0160 (3)0.0133 (3)0.0004 (2)0.0014 (2)0.0017 (2)
O40.0194 (8)0.0262 (9)0.0199 (8)0.0012 (7)0.0079 (7)0.0022 (7)
O20.0166 (8)0.0162 (8)0.0162 (8)0.0009 (6)0.0021 (6)0.0020 (6)
O10.0233 (9)0.0194 (8)0.0155 (8)0.0040 (7)0.0010 (7)0.0004 (6)
O30.0169 (8)0.0181 (8)0.0182 (8)0.0005 (6)0.0002 (6)0.0029 (6)
C230.0167 (11)0.0148 (11)0.0181 (11)0.0024 (9)0.0047 (9)0.0042 (9)
C210.0183 (11)0.0140 (11)0.0159 (11)0.0009 (9)0.0004 (9)0.0001 (8)
N10.0159 (9)0.0147 (9)0.0146 (9)0.0004 (7)0.0026 (7)0.0027 (7)
C250.0210 (12)0.0180 (11)0.0113 (10)0.0003 (9)0.0023 (9)0.0005 (8)
C180.0176 (12)0.0190 (12)0.0215 (12)0.0000 (9)0.0028 (10)0.0010 (9)
C170.0142 (11)0.0170 (11)0.0119 (10)0.0008 (9)0.0032 (9)0.0021 (8)
N30.0176 (10)0.0143 (9)0.0192 (10)0.0010 (7)0.0000 (8)0.0007 (7)
C190.0145 (11)0.0140 (10)0.0130 (10)0.0019 (8)0.0019 (9)0.0026 (8)
N20.0163 (9)0.0153 (9)0.0156 (9)0.0018 (7)0.0031 (8)0.0035 (7)
C280.0192 (12)0.0163 (11)0.0194 (12)0.0006 (9)0.0012 (9)0.0022 (9)
C240.0176 (12)0.0169 (11)0.0159 (11)0.0026 (9)0.0013 (9)0.0009 (9)
C200.0162 (11)0.0128 (10)0.0155 (11)0.0024 (9)0.0017 (9)0.0044 (8)
C260.0261 (13)0.0248 (12)0.0197 (12)0.0017 (10)0.0091 (10)0.0001 (10)
N40.0189 (10)0.0123 (9)0.0205 (10)0.0023 (8)0.0008 (8)0.0015 (8)
C290.0183 (12)0.0174 (11)0.0185 (11)0.0037 (9)0.0019 (9)0.0010 (9)
C50.0219 (12)0.0259 (13)0.0189 (12)0.0036 (10)0.0074 (10)0.0005 (10)
C270.0231 (12)0.0176 (11)0.0206 (12)0.0025 (9)0.0021 (10)0.0011 (9)
C130.0182 (12)0.0160 (11)0.0221 (12)0.0039 (9)0.0002 (10)0.0039 (9)
C40.0311 (14)0.0244 (13)0.0240 (13)0.0004 (11)0.0097 (11)0.0013 (10)
C20.0265 (13)0.0285 (13)0.0200 (12)0.0027 (10)0.0053 (10)0.0057 (10)
C30.0222 (13)0.0265 (13)0.0227 (12)0.0033 (10)0.0073 (10)0.0050 (10)
C70.0218 (14)0.0541 (18)0.0310 (14)0.0112 (12)0.0094 (11)0.0103 (13)
C300.0319 (14)0.0211 (13)0.0310 (14)0.0023 (11)0.0025 (11)0.0002 (10)
C160.0268 (13)0.0197 (12)0.0246 (13)0.0052 (10)0.0008 (10)0.0012 (10)
C90.0209 (12)0.0143 (11)0.0217 (12)0.0032 (9)0.0043 (10)0.0009 (9)
C10.0185 (12)0.0177 (11)0.0170 (11)0.0011 (9)0.0029 (9)0.0013 (9)
C310.0246 (13)0.0218 (12)0.0213 (12)0.0010 (10)0.0004 (10)0.0063 (9)
C140.0190 (13)0.0215 (12)0.0431 (16)0.0029 (10)0.0051 (11)0.0025 (11)
C150.0369 (15)0.0260 (13)0.0222 (13)0.0107 (11)0.0018 (11)0.0051 (10)
C120.0398 (16)0.0348 (15)0.0306 (14)0.0201 (12)0.0108 (12)0.0092 (12)
C60.0351 (15)0.0410 (16)0.0249 (14)0.0128 (12)0.0129 (12)0.0138 (11)
C110.0410 (17)0.0277 (14)0.0497 (18)0.0137 (12)0.0085 (14)0.0171 (13)
C100.0315 (15)0.0234 (13)0.0474 (17)0.0010 (11)0.0251 (13)0.0052 (12)
C80.0513 (18)0.0394 (16)0.0336 (15)0.0051 (13)0.0202 (14)0.0126 (12)
C220.0257 (12)0.0148 (11)0.0145 (11)0.0028 (9)0.0024 (10)0.0015 (9)
Geometric parameters (Å, º) top
P5—N71.5463 (17)P2—N31.5457 (17)
P5—N61.6798 (18)P2—N21.6735 (18)
P5—N51.6810 (17)P2—N11.6904 (17)
P5—C481.831 (2)P2—C171.827 (2)
P6—O51.4606 (15)P1—N41.6577 (19)
P6—O71.5799 (15)P1—N11.7419 (18)
P6—O61.5832 (15)P1—N21.7486 (17)
P6—C501.809 (2)P3—O11.4601 (15)
P4—N81.6616 (19)P3—O21.5826 (15)
P4—N51.7362 (18)P3—O31.5840 (15)
P4—N61.7503 (17)P3—C191.808 (2)
O8—C541.361 (2)O4—C231.364 (2)
O8—C571.430 (3)O4—C261.425 (3)
O6—C601.454 (2)O2—C291.462 (2)
O7—C581.459 (2)O3—C271.451 (2)
N6—C361.488 (3)C23—C221.386 (3)
C54—C531.387 (3)C23—C241.389 (3)
C54—C551.392 (3)C21—C221.384 (3)
C48—C491.327 (3)C21—C201.388 (3)
C48—C501.532 (3)C21—H210.9300
C55—C561.380 (3)N1—C11.486 (3)
C55—H550.9300C25—C241.375 (3)
N7—C401.479 (3)C25—C201.398 (3)
C51—C521.385 (3)C25—H250.9300
C51—C561.396 (3)C18—C171.323 (3)
C51—C501.526 (3)C18—H18A0.9300
N8—C441.484 (3)C18—H18B0.9300
N8—H8D0.82 (2)C17—C191.530 (3)
C56—H560.9300N3—C91.478 (3)
C58—C591.521 (3)C19—C201.523 (3)
C58—H58A0.9700C19—H190.9800
C58—H58B0.9700N2—C51.485 (3)
C35—C321.517 (3)C28—C291.523 (3)
C35—H35A0.9600C28—C311.524 (3)
C35—H35B0.9600C28—C271.526 (3)
C35—H35C0.9600C28—C301.531 (3)
C52—C531.390 (3)C24—H240.9300
C52—H520.9300C26—H26A0.9600
C36—C391.521 (3)C26—H26B0.9600
C36—C371.525 (3)C26—H26C0.9600
C36—C381.528 (3)N4—C131.481 (3)
C49—H49A0.9300N4—H4D0.84 (3)
C49—H49B0.9300C29—H29A0.9700
C57—H57A0.9600C29—H29B0.9700
C57—H57B0.9600C5—C71.524 (3)
C57—H57C0.9600C5—C61.527 (3)
C53—H530.9300C5—C81.527 (3)
C32—N51.483 (3)C27—H27A0.9700
C32—C331.526 (3)C27—H27B0.9700
C32—C341.527 (3)C13—C161.522 (3)
C40—C421.523 (3)C13—C141.526 (3)
C40—C431.530 (3)C13—C151.528 (3)
C40—C411.531 (3)C4—C11.521 (3)
C59—C601.524 (3)C4—H4A0.9600
C59—C621.525 (3)C4—H4B0.9600
C59—C611.532 (3)C4—H4C0.9600
C50—H500.9800C2—C11.528 (3)
C34—H34A0.9600C2—H2A0.9600
C34—H34B0.9600C2—H2B0.9600
C34—H34C0.9600C2—H2C0.9600
C60—H60A0.9700C3—C11.532 (3)
C60—H60B0.9700C3—H3A0.9600
C33—H33A0.9600C3—H3B0.9600
C33—H33B0.9600C3—H3C0.9600
C33—H33C0.9600C7—H7A0.9600
C61—H61A0.9600C7—H7B0.9600
C61—H61B0.9600C7—H7C0.9600
C61—H61C0.9600C30—H30A0.9600
C44—C471.519 (3)C30—H30B0.9600
C44—C461.527 (3)C30—H30C0.9600
C44—C451.530 (3)C16—H16A0.9600
C45—H45A0.9600C16—H16B0.9600
C45—H45B0.9600C16—H16C0.9600
C45—H45C0.9600C9—C101.515 (3)
C43—H43A0.9600C9—C111.521 (3)
C43—H43B0.9600C9—C121.523 (3)
C43—H43C0.9600C31—H31A0.9600
C37—H37A0.9600C31—H31B0.9600
C37—H37B0.9600C31—H31C0.9600
C37—H37C0.9600C14—H14A0.9600
C39—H39A0.9600C14—H14B0.9600
C39—H39B0.9600C14—H14C0.9600
C39—H39C0.9600C15—H15A0.9600
C62—H62A0.9600C15—H15B0.9600
C62—H62B0.9600C15—H15C0.9600
C62—H62C0.9600C12—H12A0.9600
C41—H41A0.9600C12—H12B0.9600
C41—H41B0.9600C12—H12C0.9600
C41—H41C0.9600C6—H6A0.9600
C38—H38A0.9600C6—H6B0.9600
C38—H38B0.9600C6—H6C0.9600
C38—H38C0.9600C11—H11A0.9600
C42—H42A0.9600C11—H11B0.9600
C42—H42B0.9600C11—H11C0.9600
C42—H42C0.9600C10—H10A0.9600
C47—H47A0.9600C10—H10B0.9600
C47—H47B0.9600C10—H10C0.9600
C47—H47C0.9600C8—H8A0.9600
C46—H46A0.9600C8—H8B0.9600
C46—H46B0.9600C8—H8C0.9600
C46—H46C0.9600C22—H220.9300
N7—P5—N6124.35 (9)N3—P2—N2124.76 (9)
N7—P5—N5124.74 (9)N3—P2—N1124.18 (9)
N6—P5—N583.15 (9)N2—P2—N183.44 (9)
N7—P5—C48104.57 (9)N3—P2—C17104.18 (9)
N6—P5—C48110.55 (9)N2—P2—C17109.04 (9)
N5—P5—C48107.94 (9)N1—P2—C17109.89 (9)
O5—P6—O7112.08 (8)N4—P1—N1104.25 (9)
O5—P6—O6112.22 (8)N4—P1—N2107.84 (9)
O7—P6—O6104.38 (8)N1—P1—N279.78 (8)
O5—P6—C50114.40 (9)O1—P3—O2111.94 (8)
O7—P6—C50106.75 (9)O1—P3—O3111.96 (8)
O6—P6—C50106.31 (9)O2—P3—O3104.51 (8)
N8—P4—N5105.48 (9)O1—P3—C19115.86 (9)
N8—P4—N6108.74 (9)O2—P3—C19105.64 (9)
N5—P4—N679.54 (8)O3—P3—C19106.07 (9)
C54—O8—C57116.51 (17)C23—O4—C26117.37 (17)
C60—O6—P6119.34 (13)C29—O2—P3117.98 (13)
C58—O7—P6118.72 (13)C27—O3—P3118.86 (13)
C36—N6—P5132.78 (14)O4—C23—C22125.48 (19)
C36—N6—P4126.17 (14)O4—C23—C24115.15 (18)
P5—N6—P497.72 (9)C22—C23—C24119.4 (2)
O8—C54—C53124.7 (2)C22—C21—C20121.72 (19)
O8—C54—C55115.91 (19)C22—C21—H21119.1
C53—C54—C55119.35 (19)C20—C21—H21119.1
C49—C48—C50121.78 (19)C1—N1—P2131.48 (14)
C49—C48—P5117.78 (16)C1—N1—P1126.07 (14)
C50—C48—P5120.34 (14)P2—N1—P197.61 (9)
C56—C55—C54120.59 (19)C24—C25—C20120.8 (2)
C56—C55—H55119.7C24—C25—H25119.6
C54—C55—H55119.7C20—C25—H25119.6
C40—N7—P5128.33 (15)C17—C18—H18A120.0
C52—C51—C56117.58 (19)C17—C18—H18B120.0
C52—C51—C50119.41 (18)H18A—C18—H18B120.0
C56—C51—C50122.96 (19)C18—C17—C19122.28 (19)
C44—N8—P4125.36 (15)C18—C17—P2118.82 (17)
C44—N8—H8D111.8 (17)C19—C17—P2118.84 (14)
P4—N8—H8D119.6 (17)C9—N3—P2129.59 (15)
C55—C56—C51121.0 (2)C20—C19—C17113.54 (16)
C55—C56—H56119.5C20—C19—P3111.75 (14)
C51—C56—H56119.5C17—C19—P3111.47 (14)
O7—C58—C59111.41 (16)C20—C19—H19106.5
O7—C58—H58A109.3C17—C19—H19106.5
C59—C58—H58A109.3P3—C19—H19106.5
O7—C58—H58B109.3C5—N2—P2133.49 (14)
C59—C58—H58B109.3C5—N2—P1126.78 (14)
H58A—C58—H58B108.0P2—N2—P197.99 (9)
C32—C35—H35A109.5C29—C28—C31110.21 (18)
C32—C35—H35B109.5C29—C28—C27109.06 (17)
H35A—C35—H35B109.5C31—C28—C27111.21 (18)
C32—C35—H35C109.5C29—C28—C30108.57 (18)
H35A—C35—H35C109.5C31—C28—C30110.11 (18)
H35B—C35—H35C109.5C27—C28—C30107.60 (18)
C51—C52—C53122.26 (19)C25—C24—C23120.63 (19)
C51—C52—H52118.9C25—C24—H24119.7
C53—C52—H52118.9C23—C24—H24119.7
N6—C36—C39109.13 (17)C21—C20—C25117.83 (19)
N6—C36—C37108.16 (18)C21—C20—C19119.76 (18)
C39—C36—C37109.28 (19)C25—C20—C19122.39 (19)
N6—C36—C38111.29 (18)O4—C26—H26A109.5
C39—C36—C38109.10 (19)O4—C26—H26B109.5
C37—C36—C38109.9 (2)H26A—C26—H26B109.5
C48—C49—H49A120.0O4—C26—H26C109.5
C48—C49—H49B120.0H26A—C26—H26C109.5
H49A—C49—H49B120.0H26B—C26—H26C109.5
O8—C57—H57A109.5C13—N4—P1126.02 (15)
O8—C57—H57B109.5C13—N4—H4D113.2 (18)
H57A—C57—H57B109.5P1—N4—H4D119.7 (18)
O8—C57—H57C109.5O2—C29—C28110.96 (16)
H57A—C57—H57C109.5O2—C29—H29A109.4
H57B—C57—H57C109.5C28—C29—H29A109.4
C54—C53—C52119.2 (2)O2—C29—H29B109.4
C54—C53—H53120.4C28—C29—H29B109.4
C52—C53—H53120.4H29A—C29—H29B108.0
N5—C32—C35110.04 (17)N2—C5—C7109.23 (18)
N5—C32—C33109.30 (17)N2—C5—C6109.41 (18)
C35—C32—C33109.83 (18)C7—C5—C6109.3 (2)
N5—C32—C34109.50 (17)N2—C5—C8110.65 (18)
C35—C32—C34108.71 (18)C7—C5—C8109.4 (2)
C33—C32—C34109.44 (18)C6—C5—C8108.9 (2)
N7—C40—C42114.31 (17)O3—C27—C28112.45 (17)
N7—C40—C43108.27 (17)O3—C27—H27A109.1
C42—C40—C43108.48 (19)C28—C27—H27A109.1
N7—C40—C41108.59 (17)O3—C27—H27B109.1
C42—C40—C41108.72 (18)C28—C27—H27B109.1
C43—C40—C41108.32 (18)H27A—C27—H27B107.8
C58—C59—C60108.60 (17)N4—C13—C16110.99 (18)
C58—C59—C62110.83 (18)N4—C13—C14107.38 (17)
C60—C59—C62111.06 (18)C16—C13—C14109.91 (19)
C58—C59—C61108.43 (18)N4—C13—C15110.10 (18)
C60—C59—C61107.80 (18)C16—C13—C15109.44 (18)
C62—C59—C61110.02 (18)C14—C13—C15108.99 (19)
C32—N5—P5132.65 (14)C1—C4—H4A109.5
C32—N5—P4127.28 (14)C1—C4—H4B109.5
P5—N5—P498.22 (9)H4A—C4—H4B109.5
C51—C50—C48113.51 (16)C1—C4—H4C109.5
C51—C50—P6110.54 (14)H4A—C4—H4C109.5
C48—C50—P6110.95 (14)H4B—C4—H4C109.5
C51—C50—H50107.2C1—C2—H2A109.5
C48—C50—H50107.2C1—C2—H2B109.5
P6—C50—H50107.2H2A—C2—H2B109.5
C32—C34—H34A109.5C1—C2—H2C109.5
C32—C34—H34B109.5H2A—C2—H2C109.5
H34A—C34—H34B109.5H2B—C2—H2C109.5
C32—C34—H34C109.5C1—C3—H3A109.5
H34A—C34—H34C109.5C1—C3—H3B109.5
H34B—C34—H34C109.5H3A—C3—H3B109.5
O6—C60—C59112.22 (17)C1—C3—H3C109.5
O6—C60—H60A109.2H3A—C3—H3C109.5
C59—C60—H60A109.2H3B—C3—H3C109.5
O6—C60—H60B109.2C5—C7—H7A109.5
C59—C60—H60B109.2C5—C7—H7B109.5
H60A—C60—H60B107.9H7A—C7—H7B109.5
C32—C33—H33A109.5C5—C7—H7C109.5
C32—C33—H33B109.5H7A—C7—H7C109.5
H33A—C33—H33B109.5H7B—C7—H7C109.5
C32—C33—H33C109.5C28—C30—H30A109.5
H33A—C33—H33C109.5C28—C30—H30B109.5
H33B—C33—H33C109.5H30A—C30—H30B109.5
C59—C61—H61A109.5C28—C30—H30C109.5
C59—C61—H61B109.5H30A—C30—H30C109.5
H61A—C61—H61B109.5H30B—C30—H30C109.5
C59—C61—H61C109.5C13—C16—H16A109.5
H61A—C61—H61C109.5C13—C16—H16B109.5
H61B—C61—H61C109.5H16A—C16—H16B109.5
N8—C44—C47111.24 (18)C13—C16—H16C109.5
N8—C44—C46107.63 (17)H16A—C16—H16C109.5
C47—C44—C46109.83 (19)H16B—C16—H16C109.5
N8—C44—C45109.44 (18)N3—C9—C10113.80 (18)
C47—C44—C45109.77 (19)N3—C9—C11109.23 (19)
C46—C44—C45108.88 (19)C10—C9—C11109.1 (2)
C44—C45—H45A109.5N3—C9—C12108.13 (17)
C44—C45—H45B109.5C10—C9—C12108.2 (2)
H45A—C45—H45B109.5C11—C9—C12108.2 (2)
C44—C45—H45C109.5N1—C1—C4109.14 (17)
H45A—C45—H45C109.5N1—C1—C2108.54 (17)
H45B—C45—H45C109.5C4—C1—C2108.54 (18)
C40—C43—H43A109.5N1—C1—C3112.22 (17)
C40—C43—H43B109.5C4—C1—C3109.96 (19)
H43A—C43—H43B109.5C2—C1—C3108.35 (18)
C40—C43—H43C109.5C28—C31—H31A109.5
H43A—C43—H43C109.5C28—C31—H31B109.5
H43B—C43—H43C109.5H31A—C31—H31B109.5
C36—C37—H37A109.5C28—C31—H31C109.5
C36—C37—H37B109.5H31A—C31—H31C109.5
H37A—C37—H37B109.5H31B—C31—H31C109.5
C36—C37—H37C109.5C13—C14—H14A109.5
H37A—C37—H37C109.5C13—C14—H14B109.5
H37B—C37—H37C109.5H14A—C14—H14B109.5
C36—C39—H39A109.5C13—C14—H14C109.5
C36—C39—H39B109.5H14A—C14—H14C109.5
H39A—C39—H39B109.5H14B—C14—H14C109.5
C36—C39—H39C109.5C13—C15—H15A109.5
H39A—C39—H39C109.5C13—C15—H15B109.5
H39B—C39—H39C109.5H15A—C15—H15B109.5
C59—C62—H62A109.5C13—C15—H15C109.5
C59—C62—H62B109.5H15A—C15—H15C109.5
H62A—C62—H62B109.5H15B—C15—H15C109.5
C59—C62—H62C109.5C9—C12—H12A109.5
H62A—C62—H62C109.5C9—C12—H12B109.5
H62B—C62—H62C109.5H12A—C12—H12B109.5
C40—C41—H41A109.5C9—C12—H12C109.5
C40—C41—H41B109.5H12A—C12—H12C109.5
H41A—C41—H41B109.5H12B—C12—H12C109.5
C40—C41—H41C109.5C5—C6—H6A109.5
H41A—C41—H41C109.5C5—C6—H6B109.5
H41B—C41—H41C109.5H6A—C6—H6B109.5
C36—C38—H38A109.5C5—C6—H6C109.5
C36—C38—H38B109.5H6A—C6—H6C109.5
H38A—C38—H38B109.5H6B—C6—H6C109.5
C36—C38—H38C109.5C9—C11—H11A109.5
H38A—C38—H38C109.5C9—C11—H11B109.5
H38B—C38—H38C109.5H11A—C11—H11B109.5
C40—C42—H42A109.5C9—C11—H11C109.5
C40—C42—H42B109.5H11A—C11—H11C109.5
H42A—C42—H42B109.5H11B—C11—H11C109.5
C40—C42—H42C109.5C9—C10—H10A109.5
H42A—C42—H42C109.5C9—C10—H10B109.5
H42B—C42—H42C109.5H10A—C10—H10B109.5
C44—C47—H47A109.5C9—C10—H10C109.5
C44—C47—H47B109.5H10A—C10—H10C109.5
H47A—C47—H47B109.5H10B—C10—H10C109.5
C44—C47—H47C109.5C5—C8—H8A109.5
H47A—C47—H47C109.5C5—C8—H8B109.5
H47B—C47—H47C109.5H8A—C8—H8B109.5
C44—C46—H46A109.5C5—C8—H8C109.5
C44—C46—H46B109.5H8A—C8—H8C109.5
H46A—C46—H46B109.5H8B—C8—H8C109.5
C44—C46—H46C109.5C21—C22—C23119.6 (2)
H46A—C46—H46C109.5C21—C22—H22120.2
H46B—C46—H46C109.5C23—C22—H22120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8D···O1i0.82 (2)2.61 (3)3.394 (2)160 (2)
N4—H4D···O5ii0.84 (3)2.58 (3)3.378 (2)158 (2)
C26—H26B···O5iii0.962.493.325 (3)145
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC31H57N4O4P3
Mr642.72
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)13.8603 (9), 15.7746 (10), 16.2606 (11)
α, β, γ (°)88.004 (1), 84.949 (1), 87.600 (1)
V3)3536.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.22 × 0.18 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.956, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
27730, 12397, 9894
Rint0.033
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.128, 1.01
No. of reflections12397
No. of parameters795
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.54, 0.28

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8D···O1i0.82 (2)2.61 (3)3.394 (2)160 (2)
N4—H4D···O5ii0.84 (3)2.58 (3)3.378 (2)158 (2)
C26—H26B···O5iii0.962.493.325 (3)145
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1.
 

Acknowledgements

The National Single Crystal Diffractometer Facility at the School of Chemistry, University of Hyderabad, funded by DST (New Delhi), and the UPE and the CAS programs of the UGC for other equipment are gratefully acknowledged. We thank Professor K. C. Kumara Swamy and Dr Srinivasulu Aitipamula for useful discussions. GG and VS thank the CSIR for fellowships.

References

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First citationKumara Swamy, K. C., Gangadhararao, G., Srinivas, V., Bhuvan Kumar, N. N., Balaraman, E. & Chakravarty, M. (2011). Inorg. Chim. Acta. In the press. doi:10.1016/j.ica.2010.12.072.  Google Scholar
First citationPraveen Kumar, K., Chakravarty, M. & Kumara Swamy, K. C. (2004). Z. Anorg. Allg. Chem. 630, 2063-2070.  Google Scholar
First citationRama Suresh, R. & Kumara Swamy, K. C. (2009). Tetrahedron Lett. 50, 6004–6007.  CrossRef CAS Google Scholar
First citationSatish Kumar, N., Praveen Kumar, K., Pavan Kumar, K. V. P., Kommana, P., Vittal, J. J. & Kumara Swamy, K. C. (2004). J. Org. Chem. 69, 1880–1889.  CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
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Volume 67| Part 5| May 2011| Pages o1212-o1213
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