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Acta Cryst. (2008). E64, o614-o615    [ doi:10.1107/S1600536808004674 ]

(3-Aminophenyl)diphenylphosphine oxide-2-propanol (1/1)

H. Mahdavi, J. Amani and J. Attar Gharamaleki

Abstract top

The title compound, C18H16NOP·C3H8O, was synthesized by the reduction of (3-nitrophenyl)diphenylphosphine oxide in the presence of 2-propanol as recrystallization solvent. There are two molecules in the asymmetric unit. Each P atom is tetracoordinated by three C and one O atom from two phenyl fragments, one aniline group and one double-bonded O atom in a distorted tetrahedral geometry. C-H...[pi] and N-H...[pi] interactions are present. In the crystal structure, a wide range of non-covalent interactions consisting of hydrogen bonding [of the types of O-H...O, N-H...O and C-H...O, with D...A distances ranging from 2.680 (3) to 3.478 (3) Å] and [pi]-[pi] [centroid-centroid distance of 3.7720 (15) Å] stacking interactions connect the various components into a supramolecular structure.

Comment top

Polymer supported phosphine reagents have wide application in organic synthesis (Chael & Buchmeiser, 2003). Usually, for preparation of these reagents, mono functional derivatives of phosphine or phosphine oxide compounds are used. But direct mono-functionalization of triphenylphosphine and triphenylphosphine oxide is one of the problematic reactions in organic synthesis and generally higher functionalization is performed and di and/or tri- substituted products are obtained. In this study, the synthesis and characterization of 3-aminophenyldiphenylphosphine oxide is reported for the first time. The molecular structure of this compound is presented in Fig. 1, while the crystal packing diagram is illustrated in Fig. 2. Selected bond lengths and bond angles are presented in Table 1. Also hydrogen bond lengths are given separately in Table 2. This complex crystallizes in the triclinic system, space group P1, with four molecules in the unit cell. There are two symmetrically independent parts in the crystal structure. To each phosphorus atom are attached three C and one O atoms from two phenyl fragments, one aniline group and one double-bonded O atom. The phosphorus-oxygen bond distances are 1.4959 (16) and 1.4974 (16) Å, and phosphorus-carbon bond distances range from 1.792 (2) to 1.803 (2) Å, which are within normal ranges (Al-Farhan, 1992). According to the bond lengths and bond angles, arrangement of the four donor atoms around each phosphorus atom is distorted tetrahedral. N1A and N1B atoms are disordered, and occupancies of positions of atoms N1A and N1B are 0.75 and 1/4, respectively.

Significant π-π stacking interactions between aromatic rings of phenyl rings with a distance of 3.7720 (15) Å [1 - x, 2 - y, -z] is observed in the prepared compound (Fig. 3) (Aghabozorg, et al., 2008).

Another noticeable feature of the title compound is the presence of C—H···π stacking interactions between C–H group of 2-propanol molecules with aromatic phenyl rings. The H···π distances (measured to the center of phenyl rings) is 2.84 Å for C3S—H3SC···Cg1 (1 - x, -y, 1 - z) and 2.93 Å for C4S—H4SC···Cg2 (2 - x, 1 - y, -z) [Cg1 and Cg2 are the centroids of C13'-C18' and C7—C12 rings, respectively] (Fig. 4) (Aghabozorg, et al., 2007).

Also, a N—H···π stacking interaction between the N–H group of aniline and phenyl rings with H···π distances of 2.45 Å for N1B—H1'D···Cg3 (1 - x, 1 - y, 1 - z) [Cg3 is the centroid for C7'-C12' ring] is observed in the title compound (Fig. 5).

In the crystal structure of the title compound, a wide range of non-covalent interactions consisting of hydrogen bonding (of the types of O—H···O, N—H···O and C—H···O with D···A ranging from 2.680 (3) Å to 3.478 (3) Å), π-π [centroid–centroid distance of 3.7720 (15) Å], C—H···π and N—H···π stacking connect the various components into a supramolecular structure.

Related literature top

For related literature, see:Aghabozorg et al. (2007); Aghabozorg et al. (2008); Al-Farhan (1992); Chael & Buchmeiser (2003); Mahdavi & Amani (2008).

Experimental top

3-aminophenyldiphenylphosphine oxide (APDPPO) was prepared from triphenylphosphine oxide according to our previous paper (Mahdavi & Amani, 2008). In this procedure, the solid product was recrystallized from 2-propanol, and 3-aminophenyldiphenylphosphine oxide was obtained as white crystals. Yield was 87% with m.p. = 166 °C.

Refinement top

Hydrogen atoms on oxygen and nitrogen atoms were found from difference Fourier maps and on carbon atoms were placed in geometrically calculated positions. All hydrogen atoms were refined in isotropic approximation in riding model with the Uiso(H) parameters equal to 1.5Ueq(O), 1.5Ueq(C) for methyl groups and to 1.2Ueq(N) and 1.2Ueq(C) for other carbon atoms where Ueq(O), Ueq(N) and Ueq(C) are the equivalent thermal parameters of the atoms to which corresponding H atoms are bonded.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacements. Ellipsoids are drawn at 50% probability level. 2-propanol groups are removed for clarity. N1A and N1B atoms are disordered and occupancies of positions of atoms N1A and N1B are 0.75 and 1/4, respectively.
[Figure 2] Fig. 2. Crystal packing diagram of the title compound (along b crystal axis). Hydrogen atoms that do not take part in hydrogen bonding are not depicted for clarity. Hydrogen bonds are shown with dashed lines.
[Figure 3] Fig. 3. π-π Stacking interactions between aromatic rings of phenyl rings with distance of 3.7720 (15) Å [1 - x, 2 - y, -z].
[Figure 4] Fig. 4. C—H···π Stacking interactions between C–H group of 2-propanol molecules with aromatic phenyl rings. The H···π distances (measured to the center of phenyl rings) is 2.84 Å for C3S—H3SC···Cg1 (1 - x, -y, 1 - z) and 2.93 Å for C4S—H4SC···Cg2 (2 - x, 1 - y, -z) [Cg1 and Cg2 are the centroids of C13'-C18' and C7—C12 rings, respectively].
[Figure 5] Fig. 5. N—H···π Stacking interactions between between N–H group of aniline and phenyl rings with H···π distances of 2.45 Å for N1B—H1'D···Cg3 (1 - x, 1 - y, 1 - z) [Cg3 is the centroid for C7'-C12' ring].
[Figure 6] Fig. 6. An interactive view of the asymmetric unit of the title compound including the disorder in the amino group position in the second molecule.
(3-Aminophenyl)diphenylphosphine oxide–2-propanol (1/1) top
Crystal data top
C18H16NOP·C3H8OZ = 4
Mr = 353.38F000 = 752
Triclinic, P1Dx = 1.226 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.0077 (9) ÅCell parameters from 342 reflections
b = 11.7682 (12) Åθ = 2.6–21.5º
c = 18.7580 (18) ŵ = 0.16 mm−1
α = 78.717 (3)ºT = 120 (2) K
β = 79.169 (3)ºPrism, colourless
γ = 86.216 (2)º0.35 × 0.18 × 0.12 mm
V = 1914.4 (3) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		6687 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Monochromator: graphiteθmax = 28.0º
T = 120(2) Kθmin = 1.8º
φ and ω scansh = −11→11
Absorption correction: nonek = −15→15
18065 measured reflectionsl = −24→24
9090 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.121  w = 1/[σ2(Fo2) + (0.01P)2 + 2.8P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
9090 reflectionsΔρmax = 1.05 e Å−3
447 parametersΔρmin = −0.71 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C18H16NOP·C3H8Oγ = 86.216 (2)º
Mr = 353.38V = 1914.4 (3) Å3
Triclinic, P1Z = 4
a = 9.0077 (9) ÅMo Kα
b = 11.7682 (12) ŵ = 0.16 mm−1
c = 18.7580 (18) ÅT = 120 (2) K
α = 78.717 (3)º0.35 × 0.18 × 0.12 mm
β = 79.169 (3)º
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		9090 independent reflections
Absorption correction: none6687 reflections with I > 2σ(I)
18065 measured reflectionsRint = 0.022
Refinement top
R[F2 > 2σ(F2)] = 0.0611 restraint
wR(F2) = 0.121H-atom parameters constrained
S = 1.03Δρmax = 1.05 e Å−3
9090 reflectionsΔρmin = −0.71 e Å−3
447 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.83874 (6)0.74162 (5)0.00875 (3)0.02776 (13)
O10.75714 (18)0.63150 (13)0.01769 (9)0.0338 (4)
C10.9933 (2)0.72363 (19)0.05909 (11)0.0268 (4)
C21.0938 (2)0.62999 (19)0.05107 (13)0.0311 (5)
H21.07940.57890.01970.037*
C31.2161 (3)0.6102 (2)0.08876 (13)0.0332 (5)
C41.2350 (2)0.6879 (2)0.13397 (12)0.0316 (5)
H41.31760.67650.15980.038*
C51.1353 (3)0.7807 (2)0.14148 (12)0.0317 (5)
H51.15050.83260.17220.038*
C61.0130 (2)0.7994 (2)0.10472 (12)0.0299 (5)
H6A0.94400.86290.11070.036*
C70.9171 (3)0.7982 (2)−0.08617 (12)0.0310 (5)
C80.8423 (3)0.7795 (2)−0.14142 (14)0.0387 (6)
H80.75540.7332−0.12910.046*
C90.8958 (3)0.8290 (3)−0.21449 (14)0.0490 (7)
H90.84530.8160−0.25220.059*
C101.0219 (3)0.8972 (2)−0.23305 (14)0.0472 (7)
H101.05680.9314−0.28320.057*
C111.0970 (3)0.9154 (2)−0.17873 (14)0.0433 (6)
H111.18400.9615−0.19130.052*
C121.0443 (3)0.8656 (2)−0.10521 (13)0.0357 (5)
H121.09600.8780−0.06780.043*
C130.7173 (2)0.85576 (19)0.04114 (12)0.0290 (5)
C140.6066 (2)0.8261 (2)0.10429 (13)0.0329 (5)
H140.59390.74710.12740.039*
C150.5157 (3)0.9118 (2)0.13308 (14)0.0384 (6)
H150.44120.89150.17620.046*
C160.5328 (3)1.0276 (2)0.09912 (14)0.0390 (6)
H160.47041.08610.11920.047*
C170.6404 (3)1.0575 (2)0.03624 (14)0.0368 (5)
H170.65121.13640.01270.044*
C180.7329 (3)0.9719 (2)0.00737 (13)0.0322 (5)
H180.80730.9928−0.03570.039*
N11.3129 (3)0.5171 (2)0.08285 (14)0.0525 (6)
H1A1.29910.46800.05500.063*
H1B1.38910.50600.10690.063*
P1'0.37636 (6)0.24882 (5)0.48023 (3)0.02777 (13)
O1'0.31222 (17)0.13607 (13)0.47740 (8)0.0318 (3)
C1'0.5759 (2)0.2540 (2)0.44592 (12)0.0307 (2)
C2'0.6575 (2)0.1492 (2)0.45007 (12)0.0307 (2)
H2'0.60650.07860.46910.037*
C3'0.8148 (2)0.1471 (2)0.42637 (12)0.0307 (2)
H3'0.90120.09470.42460.037*0.25
C4'0.8873 (3)0.2528 (2)0.39855 (14)0.0381 (5)
H4'0.99390.25310.38290.046*
C5'0.8047 (3)0.3564 (2)0.39383 (14)0.0407 (6)
H5'0.85510.42720.37420.049*
C6'0.6485 (3)0.3584 (2)0.41752 (14)0.0374 (5)
H6'0.59240.42990.41440.045*
C7'0.2912 (2)0.36956 (19)0.42528 (13)0.0310 (5)
C8'0.2197 (3)0.4637 (2)0.45372 (14)0.0374 (5)
H8'0.21670.46740.50410.045*
C9'0.1527 (3)0.5523 (2)0.40871 (16)0.0468 (7)
H9'0.10430.61660.42830.056*
C10'0.1562 (3)0.5472 (2)0.33547 (16)0.0492 (7)
H10'0.11000.60790.30500.059*
C11'0.2270 (3)0.4538 (2)0.30614 (15)0.0486 (7)
H11'0.22970.45070.25570.058*
C12'0.2938 (3)0.3649 (2)0.35120 (14)0.0406 (6)
H12'0.34160.30060.33150.049*
C13'0.3417 (3)0.27312 (19)0.57398 (12)0.0305 (5)
C14'0.2074 (3)0.2318 (2)0.61931 (14)0.0404 (6)
H14'0.13830.19360.60010.048*
C15'0.1748 (3)0.2464 (2)0.69210 (14)0.0474 (7)
H15'0.08350.21780.72270.057*
C16'0.2733 (3)0.3018 (2)0.72049 (14)0.0486 (7)
H16'0.24940.31260.77030.058*
C17'0.4081 (3)0.3420 (2)0.67617 (15)0.0449 (6)
H17'0.47150.39040.69250.054*0.75
C18'0.4429 (3)0.3276 (2)0.60274 (14)0.0367 (5)
H18'0.53530.35480.57260.044*
O1S0.2229 (2)0.05513 (18)0.36881 (11)0.0506 (5)
H1S0.25150.08020.40280.076*
O2S0.5924 (2)0.52560 (15)0.15145 (11)0.0453 (4)
H2S0.65220.54890.11190.068*
C1S0.2430 (3)−0.1203 (3)0.3254 (2)0.0687 (10)
H1SA0.1520−0.14370.36180.103*
H1SB0.3090−0.18860.31910.103*
H1SC0.2141−0.08460.27800.103*
C2S0.3203 (3)−0.0401 (3)0.3501 (2)0.0767 (12)
H2SA0.3334−0.08350.40010.092*
C3S0.4742 (3)−0.0061 (3)0.31770 (17)0.0527 (7)
H3SA0.51620.02970.35220.079*
H3SB0.47390.04960.27150.079*
H3SC0.5361−0.07470.30760.079*
C4S0.8208 (3)0.4225 (2)0.18314 (17)0.0494 (7)
H4SA0.84700.48800.20310.074*
H4SB0.86860.43070.13100.074*
H4SC0.85700.35000.21100.074*
C5S0.6520 (4)0.4207 (3)0.1897 (2)0.0605 (8)
H5S0.60960.41790.24330.073*
C6S0.5949 (4)0.3199 (3)0.1707 (3)0.0936 (15)
H6SA0.48420.32550.17830.140*
H6SB0.62690.24940.20220.140*
H6SC0.63510.31680.11880.140*
N1A0.8929 (3)0.0434 (2)0.42844 (13)0.0307 (2)0.75
H1'A0.8445−0.02180.44460.037*0.75
H1'B0.99150.04180.41360.037*0.75
N1B0.4942 (9)0.3810 (8)0.7160 (4)0.044 (2)0.25
H1'C0.46220.37870.76350.052*0.25
H1'D0.58320.40910.69470.052*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0276 (3)0.0284 (3)0.0296 (3)0.0010 (2)−0.0083 (2)−0.0085 (2)
O10.0331 (8)0.0300 (8)0.0415 (9)−0.0020 (7)−0.0116 (7)−0.0097 (7)
C10.0269 (10)0.0272 (11)0.0258 (10)−0.0008 (8)−0.0060 (8)−0.0030 (8)
C20.0322 (11)0.0272 (11)0.0374 (12)0.0011 (9)−0.0114 (9)−0.0100 (9)
C30.0311 (11)0.0279 (12)0.0422 (13)0.0018 (9)−0.0120 (10)−0.0062 (10)
C40.0292 (11)0.0354 (12)0.0315 (11)−0.0037 (9)−0.0105 (9)−0.0041 (9)
C50.0341 (12)0.0340 (12)0.0293 (11)−0.0041 (10)−0.0065 (9)−0.0097 (9)
C60.0302 (11)0.0311 (12)0.0291 (11)0.0000 (9)−0.0041 (9)−0.0084 (9)
C70.0328 (11)0.0310 (12)0.0309 (11)0.0079 (9)−0.0086 (9)−0.0099 (9)
C80.0401 (13)0.0415 (14)0.0396 (13)0.0093 (11)−0.0164 (11)−0.0142 (11)
C90.0644 (18)0.0542 (17)0.0334 (13)0.0206 (14)−0.0211 (13)−0.0157 (12)
C100.0640 (18)0.0429 (15)0.0291 (12)0.0165 (13)−0.0030 (12)−0.0046 (11)
C110.0476 (15)0.0393 (14)0.0380 (14)0.0065 (12)0.0003 (11)−0.0055 (11)
C120.0382 (13)0.0373 (13)0.0325 (12)0.0037 (10)−0.0078 (10)−0.0087 (10)
C130.0273 (10)0.0296 (12)0.0328 (11)0.0022 (9)−0.0114 (9)−0.0079 (9)
C140.0309 (11)0.0337 (12)0.0353 (12)−0.0005 (9)−0.0086 (9)−0.0072 (10)
C150.0321 (12)0.0447 (15)0.0390 (13)0.0023 (10)−0.0031 (10)−0.0136 (11)
C160.0345 (12)0.0390 (14)0.0502 (15)0.0085 (10)−0.0129 (11)−0.0222 (12)
C170.0375 (13)0.0304 (12)0.0465 (14)0.0040 (10)−0.0160 (11)−0.0104 (11)
C180.0300 (11)0.0305 (12)0.0374 (12)0.0010 (9)−0.0092 (9)−0.0068 (10)
N10.0472 (13)0.0432 (13)0.0825 (18)0.0155 (10)−0.0363 (13)−0.0306 (13)
P1'0.0287 (3)0.0265 (3)0.0286 (3)0.0001 (2)−0.0047 (2)−0.0071 (2)
O1'0.0349 (8)0.0286 (8)0.0329 (8)−0.0038 (7)−0.0064 (7)−0.0067 (7)
C1'0.0288 (6)0.0307 (6)0.0318 (6)0.0006 (5)−0.0029 (5)−0.0064 (5)
C2'0.0288 (6)0.0307 (6)0.0318 (6)0.0006 (5)−0.0029 (5)−0.0064 (5)
C3'0.0288 (6)0.0307 (6)0.0318 (6)0.0006 (5)−0.0029 (5)−0.0064 (5)
C4'0.0298 (12)0.0423 (14)0.0415 (13)−0.0042 (10)0.0001 (10)−0.0116 (11)
C5'0.0399 (13)0.0350 (13)0.0456 (14)−0.0105 (11)0.0013 (11)−0.0090 (11)
C6'0.0379 (13)0.0288 (12)0.0443 (14)−0.0012 (10)−0.0030 (11)−0.0080 (10)
C7'0.0291 (11)0.0274 (11)0.0350 (12)−0.0026 (9)−0.0048 (9)−0.0029 (9)
C8'0.0348 (12)0.0351 (13)0.0395 (13)0.0018 (10)−0.0010 (10)−0.0065 (10)
C9'0.0410 (14)0.0365 (14)0.0558 (17)0.0088 (11)−0.0005 (12)−0.0023 (12)
C10'0.0429 (15)0.0443 (16)0.0531 (17)0.0045 (12)−0.0103 (12)0.0082 (13)
C11'0.0579 (17)0.0479 (16)0.0384 (14)−0.0005 (13)−0.0147 (12)0.0015 (12)
C12'0.0488 (15)0.0361 (14)0.0373 (13)0.0011 (11)−0.0111 (11)−0.0054 (11)
C13'0.0349 (12)0.0289 (12)0.0293 (11)0.0061 (9)−0.0090 (9)−0.0081 (9)
C14'0.0374 (13)0.0453 (15)0.0367 (13)0.0040 (11)−0.0034 (10)−0.0087 (11)
C15'0.0502 (16)0.0523 (17)0.0340 (13)0.0109 (13)0.0009 (12)−0.0068 (12)
C16'0.0722 (19)0.0440 (15)0.0290 (12)0.0232 (14)−0.0110 (13)−0.0116 (11)
C17'0.0669 (18)0.0321 (13)0.0432 (14)0.0129 (12)−0.0266 (13)−0.0144 (11)
C18'0.0430 (13)0.0297 (12)0.0397 (13)0.0035 (10)−0.0131 (11)−0.0082 (10)
O1S0.0404 (10)0.0664 (13)0.0573 (12)0.0169 (9)−0.0174 (9)−0.0394 (10)
O2S0.0388 (10)0.0368 (10)0.0562 (11)0.0010 (8)−0.0118 (8)0.0042 (8)
C1S0.0431 (16)0.0442 (17)0.119 (3)−0.0012 (13)−0.0005 (18)−0.0284 (19)
C2S0.0361 (15)0.078 (2)0.133 (3)0.0082 (15)−0.0062 (18)−0.074 (2)
C3S0.0418 (15)0.0530 (17)0.0663 (19)−0.0015 (13)−0.0002 (13)−0.0269 (15)
C4S0.0445 (15)0.0444 (16)0.0588 (18)0.0089 (12)−0.0130 (13)−0.0085 (13)
C5S0.0520 (17)0.0431 (17)0.084 (2)−0.0022 (14)−0.0248 (16)0.0059 (16)
C6S0.059 (2)0.0368 (18)0.188 (5)0.0037 (16)−0.039 (3)−0.014 (2)
N1A0.0288 (6)0.0307 (6)0.0318 (6)0.0006 (5)−0.0029 (5)−0.0064 (5)
N1B0.039 (5)0.056 (6)0.037 (5)−0.011 (4)−0.008 (4)−0.006 (4)
Geometric parameters (Å, °) top
P1—O11.4974 (16)C5'—C6'1.393 (3)
P1—C71.799 (2)C5'—H5'0.9500
P1—C131.802 (2)C6'—H6'0.9500
P1—C11.803 (2)C7'—C8'1.391 (3)
C1—C61.391 (3)C7'—C12'1.397 (3)
C1—C21.393 (3)C8'—C9'1.389 (4)
C2—C31.400 (3)C8'—H8'0.9500
C2—H20.9500C9'—C10'1.381 (4)
C3—N11.364 (3)C9'—H9'0.9500
C3—C41.401 (3)C10'—C11'1.389 (4)
C4—C51.379 (3)C10'—H10'0.9500
C4—H40.9500C11'—C12'1.390 (4)
C5—C61.390 (3)C11'—H11'0.9500
C5—H50.9500C12'—H12'0.9500
C6—H6A0.9500C13'—C18'1.389 (3)
C7—C121.387 (3)C13'—C14'1.397 (3)
C7—C81.395 (3)C14'—C15'1.384 (3)
C8—C91.388 (4)C14'—H14'0.9500
C8—H80.9500C15'—C16'1.373 (4)
C9—C101.385 (4)C15'—H15'0.9500
C9—H90.9500C16'—C17'1.390 (4)
C10—C111.380 (4)C16'—H16'0.9500
C10—H100.9500C17'—N1B1.329 (4)
C11—C121.394 (3)C17'—C18'1.395 (3)
C11—H110.9500C17'—H17'0.9601
C12—H120.9500C18'—H18'0.9500
C13—C181.393 (3)O1S—C2S1.434 (3)
C13—C141.400 (3)O1S—H1S0.8400
C14—C151.385 (3)O2S—C5S1.428 (3)
C14—H140.9500O2S—H2S0.8400
C15—C161.392 (4)C1S—C2S1.403 (4)
C15—H150.9500C1S—H1SA0.9800
C16—C171.381 (4)C1S—H1SB0.9800
C16—H160.9500C1S—H1SC0.9800
C17—C181.391 (3)C2S—C3S1.454 (4)
C17—H170.9500C2S—H2SA1.0000
C18—H180.9500C3S—H3SA0.9800
N1—H1A0.8800C3S—H3SB0.9800
N1—H1B0.8800C3S—H3SC0.9800
P1'—O1'1.4959 (16)C4S—C5S1.504 (4)
P1'—C1'1.792 (2)C4S—H4SA0.9800
P1'—C7'1.803 (2)C4S—H4SB0.9800
P1'—C13'1.803 (2)C4S—H4SC0.9800
C1'—C2'1.389 (3)C5S—C6S1.453 (5)
C1'—C6'1.394 (3)C5S—H5S1.0000
C2'—C3'1.403 (3)C6S—H6SA0.9800
C2'—H2'0.9500C6S—H6SB0.9800
C3'—N1A1.364 (3)C6S—H6SC0.9800
C3'—C4'1.404 (3)N1A—H1'A0.8800
C3'—H3'0.9600N1A—H1'B0.8800
C4'—C5'1.383 (4)N1B—H1'C0.8800
C4'—H4'0.9500N1B—H1'D0.8800
O1—P1—C7112.51 (10)C5'—C6'—C1'119.0 (2)
O1—P1—C13112.56 (10)C5'—C6'—H6'120.5
C7—P1—C13105.87 (10)C1'—C6'—H6'120.5
O1—P1—C1112.47 (10)C8'—C7'—C12'119.2 (2)
C7—P1—C1106.71 (10)C8'—C7'—P1'123.25 (18)
C13—P1—C1106.21 (10)C12'—C7'—P1'117.48 (18)
C6—C1—C2120.4 (2)C9'—C8'—C7'120.2 (2)
C6—C1—P1122.05 (17)C9'—C8'—H8'119.9
C2—C1—P1117.58 (16)C7'—C8'—H8'119.9
C1—C2—C3120.8 (2)C10'—C9'—C8'120.1 (3)
C1—C2—H2119.6C10'—C9'—H9'119.9
C3—C2—H2119.6C8'—C9'—H9'119.9
N1—C3—C2121.2 (2)C9'—C10'—C11'120.5 (3)
N1—C3—C4120.6 (2)C9'—C10'—H10'119.8
C2—C3—C4118.1 (2)C11'—C10'—H10'119.8
C5—C4—C3120.8 (2)C10'—C11'—C12'119.5 (3)
C5—C4—H4119.6C10'—C11'—H11'120.3
C3—C4—H4119.6C12'—C11'—H11'120.3
C4—C5—C6120.9 (2)C11'—C12'—C7'120.5 (2)
C4—C5—H5119.5C11'—C12'—H12'119.8
C6—C5—H5119.5C7'—C12'—H12'119.8
C5—C6—C1119.0 (2)C18'—C13'—C14'119.6 (2)
C5—C6—H6A120.5C18'—C13'—P1'123.20 (18)
C1—C6—H6A120.5C14'—C13'—P1'117.21 (18)
C12—C7—C8119.4 (2)C15'—C14'—C13'120.1 (3)
C12—C7—P1121.55 (17)C15'—C14'—H14'119.9
C8—C7—P1118.90 (19)C13'—C14'—H14'119.9
C9—C8—C7119.6 (3)C16'—C15'—C14'120.6 (3)
C9—C8—H8120.2C16'—C15'—H15'119.7
C7—C8—H8120.2C14'—C15'—H15'119.7
C10—C9—C8120.7 (2)C15'—C16'—C17'119.8 (2)
C10—C9—H9119.6C15'—C16'—H16'120.1
C8—C9—H9119.6C17'—C16'—H16'120.1
C11—C10—C9120.0 (2)N1B—C17'—C16'110.4 (4)
C11—C10—H10120.0N1B—C17'—C18'129.0 (5)
C9—C10—H10120.0C16'—C17'—C18'120.3 (2)
C10—C11—C12119.6 (3)C16'—C17'—H17'121.0
C10—C11—H11120.2C18'—C17'—H17'117.9
C12—C11—H11120.2C13'—C18'—C17'119.6 (2)
C7—C12—C11120.6 (2)C13'—C18'—H18'120.2
C7—C12—H12119.7C17'—C18'—H18'120.2
C11—C12—H12119.7C2S—O1S—H1S109.5
C18—C13—C14119.2 (2)C5S—O2S—H2S109.5
C18—C13—P1122.61 (17)C2S—C1S—H1SA109.5
C14—C13—P1118.16 (17)C2S—C1S—H1SB109.5
C15—C14—C13120.0 (2)H1SA—C1S—H1SB109.5
C15—C14—H14120.0C2S—C1S—H1SC109.5
C13—C14—H14120.0H1SA—C1S—H1SC109.5
C14—C15—C16120.3 (2)H1SB—C1S—H1SC109.5
C14—C15—H15119.9C1S—C2S—O1S111.7 (3)
C16—C15—H15119.9C1S—C2S—C3S123.7 (3)
C17—C16—C15120.0 (2)O1S—C2S—C3S113.0 (3)
C17—C16—H16120.0C1S—C2S—H2SA101.5
C15—C16—H16120.0O1S—C2S—H2SA101.5
C16—C17—C18119.9 (2)C3S—C2S—H2SA101.5
C16—C17—H17120.0C2S—C3S—H3SA109.5
C18—C17—H17120.0C2S—C3S—H3SB109.5
C17—C18—C13120.5 (2)H3SA—C3S—H3SB109.5
C17—C18—H18119.8C2S—C3S—H3SC109.5
C13—C18—H18119.8H3SA—C3S—H3SC109.5
C3—N1—H1A120.0H3SB—C3S—H3SC109.5
C3—N1—H1B120.0C5S—C4S—H4SA109.5
H1A—N1—H1B120.0C5S—C4S—H4SB109.5
O1'—P1'—C1'112.49 (10)H4SA—C4S—H4SB109.5
O1'—P1'—C7'111.81 (10)C5S—C4S—H4SC109.5
C1'—P1'—C7'106.37 (11)H4SA—C4S—H4SC109.5
O1'—P1'—C13'110.02 (10)H4SB—C4S—H4SC109.5
C1'—P1'—C13'108.52 (11)O2S—C5S—C6S111.1 (3)
C7'—P1'—C13'107.41 (10)O2S—C5S—C4S112.0 (2)
C2'—C1'—C6'120.6 (2)C6S—C5S—C4S115.7 (3)
C2'—C1'—P1'117.44 (17)O2S—C5S—H5S105.8
C6'—C1'—P1'121.93 (18)C6S—C5S—H5S105.8
C1'—C2'—C3'120.5 (2)C4S—C5S—H5S105.8
C1'—C2'—H2'119.8C5S—C6S—H6SA109.5
C3'—C2'—H2'119.8C5S—C6S—H6SB109.5
N1A—C3'—C2'119.8 (2)H6SA—C6S—H6SB109.5
N1A—C3'—C4'121.6 (2)C5S—C6S—H6SC109.5
C2'—C3'—C4'118.6 (2)H6SA—C6S—H6SC109.5
C2'—C3'—H3'141.5H6SB—C6S—H6SC109.5
C4'—C3'—H3'99.8C3'—N1A—H1'A120.0
C5'—C4'—C3'120.5 (2)C3'—N1A—H1'B120.0
C5'—C4'—H4'119.8H1'A—N1A—H1'B120.0
C3'—C4'—H4'119.8C17'—N1B—H1'C120.0
C4'—C5'—C6'120.9 (2)C17'—N1B—H1'D120.0
C4'—C5'—H5'119.6H1'C—N1B—H1'D120.0
C6'—C5'—H5'119.6
O1—P1—C1—C6−131.38 (18)C7'—P1'—C1'—C2'−148.70 (18)
C7—P1—C1—C6104.79 (19)C13'—P1'—C1'—C2'96.01 (19)
C13—P1—C1—C6−7.8 (2)O1'—P1'—C1'—C6'155.42 (19)
O1—P1—C1—C248.4 (2)C7'—P1'—C1'—C6'32.7 (2)
C7—P1—C1—C2−75.40 (19)C13'—P1'—C1'—C6'−82.6 (2)
C13—P1—C1—C2171.98 (17)C6'—C1'—C2'—C3'0.6 (3)
C6—C1—C2—C30.1 (3)P1'—C1'—C2'—C3'−177.99 (17)
P1—C1—C2—C3−179.68 (18)C1'—C2'—C3'—N1A−177.8 (2)
C1—C2—C3—N1178.2 (2)C1'—C2'—C3'—C4'0.0 (3)
C1—C2—C3—C4−0.7 (3)N1A—C3'—C4'—C5'176.9 (2)
N1—C3—C4—C5−178.5 (2)C2'—C3'—C4'—C5'−0.8 (4)
C2—C3—C4—C50.4 (3)C3'—C4'—C5'—C6'1.0 (4)
C3—C4—C5—C60.3 (3)C4'—C5'—C6'—C1'−0.3 (4)
C4—C5—C6—C1−0.9 (3)C2'—C1'—C6'—C5'−0.5 (4)
C2—C1—C6—C50.6 (3)P1'—C1'—C6'—C5'178.07 (19)
P1—C1—C6—C5−179.56 (17)O1'—P1'—C7'—C8'123.4 (2)
O1—P1—C7—C12−152.32 (18)C1'—P1'—C7'—C8'−113.4 (2)
C13—P1—C7—C1284.3 (2)C13'—P1'—C7'—C8'2.6 (2)
C1—P1—C7—C12−28.5 (2)O1'—P1'—C7'—C12'−54.4 (2)
O1—P1—C7—C831.6 (2)C1'—P1'—C7'—C12'68.8 (2)
C13—P1—C7—C8−91.7 (2)C13'—P1'—C7'—C12'−175.16 (19)
C1—P1—C7—C8155.44 (18)C12'—C7'—C8'—C9'−0.4 (4)
C12—C7—C8—C9−0.3 (3)P1'—C7'—C8'—C9'−178.18 (19)
P1—C7—C8—C9175.80 (19)C7'—C8'—C9'—C10'0.2 (4)
C7—C8—C9—C10−0.3 (4)C8'—C9'—C10'—C11'−0.2 (4)
C8—C9—C10—C110.8 (4)C9'—C10'—C11'—C12'0.3 (4)
C9—C10—C11—C12−0.5 (4)C10'—C11'—C12'—C7'−0.5 (4)
C8—C7—C12—C110.6 (3)C8'—C7'—C12'—C11'0.6 (4)
P1—C7—C12—C11−175.48 (18)P1'—C7'—C12'—C11'178.5 (2)
C10—C11—C12—C7−0.1 (4)O1'—P1'—C13'—C18'144.78 (19)
O1—P1—C13—C18−145.04 (18)C1'—P1'—C13'—C18'21.3 (2)
C7—P1—C13—C18−21.7 (2)C7'—P1'—C13'—C18'−93.3 (2)
C1—P1—C13—C1891.5 (2)O1'—P1'—C13'—C14'−33.6 (2)
O1—P1—C13—C1437.2 (2)C1'—P1'—C13'—C14'−157.07 (18)
C7—P1—C13—C14160.52 (17)C7'—P1'—C13'—C14'88.3 (2)
C1—P1—C13—C14−86.28 (19)C18'—C13'—C14'—C15'0.8 (4)
C18—C13—C14—C15−0.9 (3)P1'—C13'—C14'—C15'179.2 (2)
P1—C13—C14—C15176.95 (18)C13'—C14'—C15'—C16'0.3 (4)
C13—C14—C15—C160.6 (4)C14'—C15'—C16'—C17'−1.1 (4)
C14—C15—C16—C170.3 (4)C15'—C16'—C17'—N1B−173.1 (5)
C15—C16—C17—C18−0.8 (4)C15'—C16'—C17'—C18'0.8 (4)
C16—C17—C18—C130.4 (3)C14'—C13'—C18'—C17'−1.0 (3)
C14—C13—C18—C170.4 (3)P1'—C13'—C18'—C17'−179.36 (18)
P1—C13—C18—C17−177.34 (17)N1B—C17'—C18'—C13'172.9 (6)
O1'—P1'—C1'—C2'−26.0 (2)C16'—C17'—C18'—C13'0.2 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.882.112.982 (3)172
N1—H1B···O2Sii0.882.193.051 (3)165
O1S—H1S···O1'0.841.842.680 (3)179
O2S—H2S···O10.841.952.770 (3)167
N1A—H1'A···O1'iii0.882.162.970 (3)154
N1A—H1'B···O1Sii0.882.102.975 (3)173
N1B—H1'C···O2Siv0.882.102.869 (3)146
C9—H9···O1Sv0.952.563.288 (3)134
C14—H14···O2S0.952.563.478 (3)163
C3S—H3SC···Cg1iii0.982.843.741 (4)153
C4S—H4SC···Cg2i0.982.933.645 (3)131
N1B—H1'D···Cg3iv0.882.453.296 (8)161
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z.
Table 1
Selected geometric parameters (Å, °) top
P1—O11.4974 (16)P1'—O1'1.4959 (16)
P1—C71.799 (2)P1'—C1'1.792 (2)
P1—C131.802 (2)P1'—C7'1.803 (2)
P1—C11.803 (2)P1'—C13'1.803 (2)
O1—P1—C7112.51 (10)O1'—P1'—C1'112.49 (10)
O1—P1—C13112.56 (10)O1'—P1'—C7'111.81 (10)
C7—P1—C13105.87 (10)C1'—P1'—C7'106.37 (11)
O1—P1—C1112.47 (10)O1'—P1'—C13'110.02 (10)
C7—P1—C1106.71 (10)C1'—P1'—C13'108.52 (11)
C13—P1—C1106.21 (10)C7'—P1'—C13'107.41 (10)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.882.112.982 (3)172
N1—H1B···O2Sii0.882.193.051 (3)165
O1S—H1S···O1'0.841.842.680 (3)179
O2S—H2S···O10.841.952.770 (3)167
N1A—H1'A···O1'iii0.882.162.970 (3)154
N1A—H1'B···O1Sii0.882.102.975 (3)173
N1B—H1'C···O2Siv0.882.102.869 (3)146
C9—H9···O1Sv0.952.563.288 (3)134
C14—H14···O2S0.952.563.478 (3)163
C3S—H3SC···Cg1iii0.982.843.741 (4)153
C4S—H4SC···Cg2i0.982.933.645 (3)131
N1B—H1'D···Cg3iv0.882.453.296 (8)161
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+1, −z.
references
References top

Aghabozorg, H., Attar Gharamaleki, J., Daneshvar, S., Ghadermazi, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m187–m188.

Aghabozorg, H., Attar Gharamaleki, J., Motyeian, E. & Ghadermazi, M. (2007). Acta Cryst. E63, m2793–m2794.

Al-Farhan, K. A. (1992). J. Cryst. Spect. Res. 22(6), 687–689.

Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.

Chael, M. & Buchmeiser, R. (2003). In Polymeric Materials in Organic Synthesis and Catalysis. City of publication?: Wiley.

Mahdavi, H. & Amani, J. (2008). Tetrahedron Lett. Accepted. Any update?

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.