Redetermined structure of diphenyl­phospho­nimidotriphenyl­phospho­rane: location of the hydrogen atoms and analysis of the inter­molecular inter­actions

Betz, R.; Gerber, T.; Hosten, E.; Schalekamp, H.

doi:10.1107/S1600536811011500

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1028-o1029

doi:10.1107/S1600536811011500

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Redetermined structure of diphenylphosphonimidotriphenylphosphorane: location of the hydrogen atoms and analysis of the intermolecular interactions

Richard Betz,^a ^* Thomas Gerber,^a Eric Hosten ^a and Henk Schalekamp ^a

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 25 March 2011; accepted 28 March 2011; online 7 April 2011)

The title compound, C₃₀H₂₅NOP₂, is a bulky phosphazene derivative. Its previous crystal structure [Cameron et al. (1979 ). Acta Cryst. B35, 1373–1377] is confirmed and its H atoms have been located in the present study. The formal P=N double bond is about 0.05 Å shorter than the P—N single bond and the large P=N—P bond angle reflects the steric strain in the molecule. An intramolecular C—H⋯O interaction occurs. In the crystal, short C—H⋯O contacts connect the molecules into chains propagating in [011], which are cross-linked via C—H⋯π interactions, generating a three-dimensional network. Aromatic π–π stacking also occurs [shortest centroid–centroid separation = 3.6012 (11) Å].

Related literature

For the previous structure determination, see: Cameron et al. (1979). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₀H₂₅NOP₂
M_r = 477.45
Orthorhombic, P n a 2₁
a = 17.6607 (12) Å
b = 15.1593 (10) Å
c = 8.9192 (6) Å
V = 2387.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 200 K
0.88 × 0.42 × 0.31 mm

Data collection

Bruker APEXII CCD diffractometer
12511 measured reflections
4498 independent reflections
4348 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.076
S = 1.11
4498 reflections
307 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1332 Friedel pairs
Flack parameter: −0.03 (6)

Table 1
Selected geometric parameters (Å, °)

P1—N1	1.6014 (13)
P2—N1	1.5532 (13)

P2—N1—P1	146.35 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C32—H32⋯O1	0.95	2.34	3.257 (2)	163
C43—H43⋯O1ⁱ	0.95	2.34	3.257 (2)	162
C45—H45⋯Cg1ⁱⁱ	0.95	2.92	3.846 (2)	165
C55—H55⋯Cg2ⁱⁱⁱ	0.95	2.73	3.644 (2)	163
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) $[-x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011500/hb5826sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011500/hb5826Isup2.hkl

checkCIF report

Comment top

For many main group elements as well as transition and rare earth metals, preferred coordination numbers in coordination compounds are apparent. While coordination numbers of 4, 6 and 8 have been found to be dominant in most cases and, as a consequence, vast structural information has been collected for such compounds in solution and in the solid state, information about other coordination numbers is comparatively limited. Especially for smaller coordination numbers the literature is scant or hitherto completely unknown for many elements. One reason for this certainly is that sometimes challenging synthesis procedures have to be followed and, thus, a general but simple synthetic protocol is desireable. Since such compounds may act as versatile and potent catalysts in many industrial processes and might even show interesting pharmacological properties, we were interested in developing an easy-access-route for their synthesis. Applying bulky ligands might open up a pathway in this aspect. In order to be able to compare metrical parameters in envisioned reaction products, we determined the crystal structure of the title compound. The latter one has already been reported earlier (Cameron et al. (1979)), however, no hydrogen atoms were included in the refinement thus ruling out the possibility to assess the role of C–H···X contacts.

The length of the N–P bonds deviate by 0.05 Å with the – formal – P–N-double bond found at around 1.55 Å. The P–N–P angle was measured at more than 146 °. The marked widening of this angle in comparison to the value expected for a sp²-hybridized nitrogen atom can be explained by the repulsive interaction of the phenyl-moieties on both P atoms. The phenyl groups on each phosphorus atom are approximately orientated perpendicular to each other. The least-squares planes defined by their carbon atoms intersect at an angle of 82.19 (6) ° in case of the P(O)Ph₂-moiety and at angles of 79.82 (5) °, 80.91 (6) ° and 83.28 (6) °, respectively, in case of the PPh₃-moiety. Due to the formation of an intramolecular C–H···O contact (see below), the least-squares plane defined by the P(O)–N–P motif encloses an angle of only 29.40 (9) ° with one of the aromatic carbocycles on the PPh₃-moiety (Fig. 1). For the same reason, both phenyl groups of the P(O)Ph₂-moiety adopt a slightly ecliptic conformation with respect to the P(O) motif, the respective dihedral angles were found at about 19 ° and 26 °.

In the crystal structure, intermolecular C–H···O contacts are present whose range falls by more than 0.3 Å below the sum of van-der-Waals radii of the atoms participating. These can be observed between one of the H atoms in meta-position of a phenyl group on the PPh₃-moiety and the O atom of the P(O)Ph₂-moiety and connect the molecules to infinte chains along [0 1 1] (Fig. 2). Furthermore, intramolecular C–H···O contacts invariably involving hydrogen atoms in ortho-position on one of the phenyl groups of the PPh₃-moiety as well as both phenyl groups of the P(O)Ph₂-moiety are present. However, the latter two ones are not very pronounced. Additionally, a set of C–H···π contacts are evident involving H atoms and aromatic systems both on the PPh₃-moiety as well as the P(O)Ph₂-moiety. Their details are listed in Table 1 (with C_g(1) = C41···C46, C_g(2) = C31···C36 and C_g(3) = C11···C16). In total, the C–H···O contacts as well as the C–H···π contacts connect the molecules to a three dimensional network. In terms of graph-set analysis (Etter et al. (1990); Bernstein et al. (1995)), the intermolecular C–H···O contacts can be assigned a C¹₁(8) descriptor on the unitary level while the intramolecular C–H···O contact involving the phenyl group of the PPh₃-moiety necessitates a S¹₁(7) descriptor. For the other two intramolecular C–H···O contacts, a S¹₁(5) each is feasible. An analysis of C_g···C_g interactions shows the closest distance between two centers of gravity to occur between a phenyl group on the PPh₃-moiety and a phenyl group on the P(O)Ph₂-moiety. The distance was measured at 3.6012 (11) Å.

The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For the previous structure determination, see: Cameron et al. (1979). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

The compound was obtained commercially (Aldrich). A colourles block suitable for the X-ray diffraction study were taken directly from the provided material.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, with anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [-1 0 0]. Symmetry operators: i -x + 1/2, y - 1/2, z + 1/2; ii -x + 1/2, y + 1/2, z - 1/2.
	Fig. 3. Crystal packing of the title compound, viewed along [0 0 - 1] (anisotropic displacement ellipsoids drawn at 50% probability level).

Diphenylphosphonimidotriphenylphosphorane top

Crystal data top

C₃₀H₂₅NOP₂	D_x = 1.328 Mg m⁻³
M_r = 477.45	Melting point = 442–445 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9977 reflections
a = 17.6607 (12) Å	θ = 2.7–28.3°
b = 15.1593 (10) Å	µ = 0.21 mm⁻¹
c = 8.9192 (6) Å	T = 200 K
V = 2387.9 (3) Å³	Block, colourless
Z = 4	0.88 × 0.42 × 0.31 mm
F(000) = 1000

Data collection top

Bruker APEXII CCD diffractometer	4348 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 28.3°, θ_min = 2.9°
ϕ and ω scans	h = −22→23
12511 measured reflections	k = −20→16
4498 independent reflections	l = −7→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0452P)² + 0.5077P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
4498 reflections	Δρ_max = 0.21 e Å⁻³
307 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1332 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (6)

Crystal data top

C₃₀H₂₅NOP₂	V = 2387.9 (3) Å³
M_r = 477.45	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 17.6607 (12) Å	µ = 0.21 mm⁻¹
b = 15.1593 (10) Å	T = 200 K
c = 8.9192 (6) Å	0.88 × 0.42 × 0.31 mm

Data collection top

Bruker APEXII CCD diffractometer	4348 reflections with I > 2σ(I)
12511 measured reflections	R_int = 0.021
4498 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.21 e Å⁻³
S = 1.11	Δρ_min = −0.25 e Å⁻³
4498 reflections	Absolute structure: Flack (1983), 1332 Friedel pairs
307 parameters	Absolute structure parameter: −0.03 (6)
1 restraint

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

	x	y	z	U_iso*/U_eq
P1	0.083912 (19)	0.16050 (2)	0.55082 (5)	0.02138 (9)
P2	0.227542 (18)	0.05280 (2)	0.53590 (6)	0.02115 (9)
O1	0.08330 (6)	0.21271 (8)	0.40946 (15)	0.0276 (3)
N1	0.15673 (7)	0.10297 (9)	0.59418 (19)	0.0272 (3)
C11	0.06899 (9)	0.23246 (11)	0.7102 (2)	0.0251 (3)
C12	0.02931 (10)	0.31087 (11)	0.6883 (3)	0.0327 (4)
H12	0.0132	0.3268	0.5903	0.039*
C13	0.01304 (11)	0.36602 (13)	0.8084 (3)	0.0420 (5)
H13	−0.0139	0.4194	0.7924	0.050*
C14	0.03602 (12)	0.34320 (14)	0.9502 (3)	0.0440 (5)
H14	0.0252	0.3813	1.0321	0.053*
C15	0.07484 (12)	0.26496 (15)	0.9752 (3)	0.0426 (5)
H15	0.0898	0.2489	1.0738	0.051*
C16	0.09162 (10)	0.21044 (13)	0.8546 (2)	0.0336 (4)
H16	0.1190	0.1573	0.8710	0.040*
C21	0.00231 (8)	0.08902 (9)	0.5576 (2)	0.0228 (3)
C22	−0.05883 (9)	0.10711 (11)	0.4654 (2)	0.0294 (4)
H22	−0.0563	0.1549	0.3968	0.035*
C23	−0.12411 (10)	0.05546 (13)	0.4728 (2)	0.0358 (4)
H23	−0.1663	0.0687	0.4106	0.043*
C24	−0.12731 (9)	−0.01467 (12)	0.5705 (2)	0.0357 (4)
H24	−0.1714	−0.0504	0.5741	0.043*
C25	−0.06683 (10)	−0.03348 (12)	0.6635 (2)	0.0331 (4)
H25	−0.0693	−0.0819	0.7309	0.040*
C26	−0.00227 (9)	0.01904 (11)	0.6576 (2)	0.0286 (4)
H26	0.0391	0.0069	0.7225	0.034*
C31	0.29089 (9)	0.11812 (11)	0.4214 (2)	0.0250 (3)
C32	0.26144 (10)	0.18326 (12)	0.3296 (2)	0.0352 (4)
H32	0.2087	0.1958	0.3315	0.042*
C33	0.30909 (12)	0.23043 (13)	0.2347 (3)	0.0421 (5)
H33	0.2887	0.2747	0.1711	0.051*
C34	0.38560 (11)	0.21312 (13)	0.2327 (2)	0.0378 (4)
H34	0.4179	0.2455	0.1676	0.045*
C35	0.41530 (10)	0.14935 (15)	0.3242 (3)	0.0404 (5)
H35	0.4681	0.1377	0.3222	0.048*
C36	0.36879 (10)	0.10175 (14)	0.4197 (2)	0.0350 (4)
H36	0.3898	0.0581	0.4839	0.042*
C41	0.28149 (8)	0.01741 (10)	0.6966 (2)	0.0222 (3)
C42	0.31729 (9)	−0.06444 (11)	0.7022 (2)	0.0288 (4)
H42	0.3146	−0.1031	0.6186	0.035*
C43	0.35690 (10)	−0.08954 (12)	0.8295 (2)	0.0340 (4)
H43	0.3809	−0.1456	0.8334	0.041*
C44	0.36148 (10)	−0.03317 (14)	0.9506 (2)	0.0375 (4)
H44	0.3886	−0.0504	1.0378	0.045*
C45	0.32647 (11)	0.04883 (13)	0.9453 (2)	0.0372 (4)
H45	0.3301	0.0878	1.0284	0.045*
C46	0.28624 (9)	0.07380 (11)	0.8190 (2)	0.0290 (4)
H46	0.2618	0.1296	0.8161	0.035*
C51	0.20882 (9)	−0.04527 (11)	0.4262 (2)	0.0252 (3)
C52	0.25999 (10)	−0.07830 (13)	0.3230 (2)	0.0335 (4)
H52	0.3072	−0.0494	0.3088	0.040*
C53	0.24317 (12)	−0.15319 (13)	0.2399 (3)	0.0402 (5)
H53	0.2786	−0.1757	0.1695	0.048*
C54	0.17403 (12)	−0.19490 (12)	0.2607 (3)	0.0396 (5)
H54	0.1617	−0.2456	0.2030	0.047*
C55	0.12324 (11)	−0.16321 (12)	0.3645 (3)	0.0369 (4)
H55	0.0763	−0.1926	0.3792	0.044*
C56	0.14026 (9)	−0.08887 (11)	0.4474 (2)	0.0310 (4)
H56	0.1050	−0.0674	0.5192	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01837 (15)	0.02043 (17)	0.0254 (2)	0.00090 (11)	0.00122 (16)	0.00224 (17)
P2	0.01691 (14)	0.02080 (17)	0.0257 (2)	0.00025 (12)	−0.00016 (17)	0.00197 (17)
O1	0.0292 (6)	0.0257 (6)	0.0280 (7)	0.0001 (4)	0.0027 (5)	0.0053 (5)
N1	0.0199 (5)	0.0267 (6)	0.0351 (8)	0.0034 (5)	0.0010 (5)	0.0037 (6)
C11	0.0199 (6)	0.0245 (8)	0.0308 (9)	−0.0035 (6)	0.0018 (6)	−0.0028 (7)
C12	0.0298 (8)	0.0289 (8)	0.0395 (11)	0.0029 (6)	0.0048 (8)	0.0001 (8)
C13	0.0428 (10)	0.0290 (9)	0.0542 (14)	0.0017 (8)	0.0125 (10)	−0.0085 (9)
C14	0.0450 (10)	0.0417 (11)	0.0452 (13)	−0.0110 (8)	0.0144 (10)	−0.0188 (10)
C15	0.0421 (10)	0.0524 (12)	0.0333 (11)	−0.0127 (9)	−0.0004 (9)	−0.0061 (9)
C16	0.0309 (8)	0.0361 (9)	0.0338 (10)	−0.0025 (7)	−0.0022 (8)	−0.0020 (8)
C21	0.0199 (6)	0.0213 (6)	0.0271 (9)	0.0013 (5)	0.0022 (6)	−0.0025 (7)
C22	0.0264 (7)	0.0307 (8)	0.0312 (9)	0.0017 (6)	−0.0034 (7)	−0.0001 (7)
C23	0.0232 (7)	0.0444 (10)	0.0398 (11)	0.0007 (7)	−0.0051 (7)	−0.0080 (9)
C24	0.0265 (7)	0.0418 (9)	0.0388 (11)	−0.0100 (6)	0.0079 (7)	−0.0124 (8)
C25	0.0346 (8)	0.0314 (8)	0.0332 (10)	−0.0077 (7)	0.0073 (8)	0.0006 (8)
C26	0.0258 (7)	0.0317 (8)	0.0282 (9)	−0.0022 (6)	0.0002 (7)	0.0028 (7)
C31	0.0232 (7)	0.0257 (7)	0.0262 (8)	−0.0035 (6)	0.0031 (6)	−0.0017 (7)
C32	0.0318 (8)	0.0326 (9)	0.0411 (12)	0.0050 (7)	0.0094 (8)	0.0071 (8)
C33	0.0481 (10)	0.0323 (9)	0.0460 (12)	0.0030 (8)	0.0174 (10)	0.0110 (9)
C34	0.0417 (10)	0.0398 (10)	0.0320 (10)	−0.0152 (8)	0.0124 (8)	−0.0041 (8)
C35	0.0238 (8)	0.0626 (13)	0.0348 (11)	−0.0106 (8)	0.0025 (8)	−0.0013 (10)
C36	0.0243 (7)	0.0480 (10)	0.0328 (10)	−0.0023 (7)	−0.0012 (7)	0.0056 (8)
C41	0.0186 (6)	0.0234 (7)	0.0247 (8)	−0.0013 (5)	−0.0001 (6)	0.0030 (6)
C42	0.0257 (7)	0.0273 (8)	0.0335 (10)	0.0035 (6)	−0.0004 (7)	−0.0010 (7)
C43	0.0290 (8)	0.0324 (8)	0.0407 (11)	0.0042 (6)	−0.0041 (8)	0.0091 (8)
C44	0.0316 (8)	0.0503 (11)	0.0305 (10)	0.0008 (7)	−0.0061 (7)	0.0094 (9)
C45	0.0346 (9)	0.0451 (10)	0.0319 (10)	−0.0010 (7)	−0.0040 (8)	−0.0076 (9)
C46	0.0255 (7)	0.0279 (8)	0.0335 (10)	0.0004 (6)	−0.0005 (7)	−0.0030 (8)
C51	0.0232 (7)	0.0239 (7)	0.0284 (9)	0.0016 (5)	−0.0052 (6)	0.0014 (6)
C52	0.0289 (8)	0.0379 (9)	0.0339 (11)	0.0013 (7)	−0.0019 (7)	−0.0064 (8)
C53	0.0417 (10)	0.0382 (10)	0.0407 (12)	0.0087 (8)	−0.0027 (9)	−0.0109 (9)
C54	0.0471 (10)	0.0272 (8)	0.0443 (12)	0.0033 (7)	−0.0163 (9)	−0.0032 (8)
C55	0.0346 (8)	0.0282 (8)	0.0480 (12)	−0.0054 (7)	−0.0104 (9)	0.0039 (8)
C56	0.0265 (7)	0.0286 (8)	0.0379 (10)	−0.0019 (6)	−0.0023 (7)	0.0012 (8)

Geometric parameters (Å, º) top

P1—O1	1.4887 (13)	C32—C33	1.392 (3)
P1—N1	1.6014 (13)	C32—H32	0.9500
P1—C21	1.8040 (15)	C33—C34	1.377 (3)
P1—C11	1.8109 (18)	C33—H33	0.9500
P2—N1	1.5532 (13)	C34—C35	1.370 (3)
P2—C41	1.8027 (17)	C34—H34	0.9500
P2—C31	1.8099 (17)	C35—C36	1.386 (3)
P2—C51	1.8099 (17)	C35—H35	0.9500
C11—C16	1.389 (3)	C36—H36	0.9500
C11—C12	1.394 (2)	C41—C46	1.389 (2)
C12—C13	1.389 (3)	C41—C42	1.394 (2)
C12—H12	0.9500	C42—C43	1.387 (3)
C13—C14	1.373 (4)	C42—H42	0.9500
C13—H13	0.9500	C43—C44	1.380 (3)
C14—C15	1.388 (3)	C43—H43	0.9500
C14—H14	0.9500	C44—C45	1.389 (3)
C15—C16	1.388 (3)	C44—H44	0.9500
C15—H15	0.9500	C45—C46	1.384 (3)
C16—H16	0.9500	C45—H45	0.9500
C21—C22	1.385 (2)	C46—H46	0.9500
C21—C26	1.388 (2)	C51—C52	1.384 (3)
C22—C23	1.395 (2)	C51—C56	1.392 (2)
C22—H22	0.9500	C52—C53	1.388 (3)
C23—C24	1.376 (3)	C52—H52	0.9500
C23—H23	0.9500	C53—C54	1.387 (3)
C24—C25	1.382 (3)	C53—H53	0.9500
C24—H24	0.9500	C54—C55	1.375 (3)
C25—C26	1.392 (2)	C54—H54	0.9500
C25—H25	0.9500	C55—C56	1.381 (3)
C26—H26	0.9500	C55—H55	0.9500
C31—C32	1.384 (3)	C56—H56	0.9500
C31—C36	1.398 (2)

O1—P1—N1	120.00 (8)	C31—C32—C33	119.94 (17)
O1—P1—C21	110.00 (8)	C31—C32—H32	120.0
N1—P1—C21	107.83 (7)	C33—C32—H32	120.0
O1—P1—C11	110.08 (7)	C34—C33—C32	120.2 (2)
N1—P1—C11	104.80 (8)	C34—C33—H33	119.9
C21—P1—C11	102.66 (7)	C32—C33—H33	119.9
N1—P2—C41	107.77 (8)	C35—C34—C33	120.16 (18)
N1—P2—C31	114.75 (7)	C35—C34—H34	119.9
C41—P2—C31	106.55 (7)	C33—C34—H34	119.9
N1—P2—C51	115.84 (7)	C34—C35—C36	120.47 (17)
C41—P2—C51	106.37 (8)	C34—C35—H35	119.8
C31—P2—C51	104.91 (8)	C36—C35—H35	119.8
P2—N1—P1	146.35 (12)	C35—C36—C31	119.81 (18)
C16—C11—C12	118.64 (17)	C35—C36—H36	120.1
C16—C11—P1	122.75 (13)	C31—C36—H36	120.1
C12—C11—P1	118.51 (15)	C46—C41—C42	119.50 (16)
C13—C12—C11	120.6 (2)	C46—C41—P2	118.28 (12)
C13—C12—H12	119.7	C42—C41—P2	122.22 (14)
C11—C12—H12	119.7	C43—C42—C41	120.15 (18)
C14—C13—C12	119.86 (19)	C43—C42—H42	119.9
C14—C13—H13	120.1	C41—C42—H42	119.9
C12—C13—H13	120.1	C44—C43—C42	120.04 (17)
C13—C14—C15	120.6 (2)	C44—C43—H43	120.0
C13—C14—H14	119.7	C42—C43—H43	120.0
C15—C14—H14	119.7	C43—C44—C45	120.09 (18)
C14—C15—C16	119.3 (2)	C43—C44—H44	120.0
C14—C15—H15	120.3	C45—C44—H44	120.0
C16—C15—H15	120.3	C46—C45—C44	120.07 (18)
C15—C16—C11	120.92 (18)	C46—C45—H45	120.0
C15—C16—H16	119.5	C44—C45—H45	120.0
C11—C16—H16	119.5	C45—C46—C41	120.15 (16)
C22—C21—C26	119.16 (14)	C45—C46—H46	119.9
C22—C21—P1	118.95 (13)	C41—C46—H46	119.9
C26—C21—P1	121.82 (12)	C52—C51—C56	119.09 (16)
C21—C22—C23	120.35 (17)	C52—C51—P2	122.51 (13)
C21—C22—H22	119.8	C56—C51—P2	118.39 (14)
C23—C22—H22	119.8	C51—C52—C53	120.76 (17)
C24—C23—C22	119.84 (17)	C51—C52—H52	119.6
C24—C23—H23	120.1	C53—C52—H52	119.6
C22—C23—H23	120.1	C54—C53—C52	119.33 (19)
C23—C24—C25	120.51 (15)	C54—C53—H53	120.3
C23—C24—H24	119.7	C52—C53—H53	120.3
C25—C24—H24	119.7	C55—C54—C53	120.31 (18)
C24—C25—C26	119.50 (18)	C55—C54—H54	119.8
C24—C25—H25	120.3	C53—C54—H54	119.8
C26—C25—H25	120.3	C54—C55—C56	120.23 (18)
C21—C26—C25	120.63 (16)	C54—C55—H55	119.9
C21—C26—H26	119.7	C56—C55—H55	119.9
C25—C26—H26	119.7	C55—C56—C51	120.27 (18)
C32—C31—C36	119.36 (16)	C55—C56—H56	119.9
C32—C31—P2	119.46 (12)	C51—C56—H56	119.9
C36—C31—P2	121.14 (14)

C41—P2—N1—P1	173.79 (15)	C41—P2—C31—C36	29.82 (17)
C31—P2—N1—P1	55.30 (19)	C51—P2—C31—C36	−82.72 (17)
C51—P2—N1—P1	−67.26 (19)	C36—C31—C32—C33	1.3 (3)
O1—P1—N1—P2	−25.4 (2)	P2—C31—C32—C33	−176.30 (16)
C21—P1—N1—P2	101.52 (17)	C31—C32—C33—C34	−0.6 (3)
C11—P1—N1—P2	−149.62 (16)	C32—C33—C34—C35	0.0 (3)
O1—P1—C11—C16	−157.41 (13)	C33—C34—C35—C36	−0.1 (3)
N1—P1—C11—C16	−27.08 (16)	C34—C35—C36—C31	0.8 (3)
C21—P1—C11—C16	85.50 (15)	C32—C31—C36—C35	−1.4 (3)
O1—P1—C11—C12	26.37 (15)	P2—C31—C36—C35	176.14 (16)
N1—P1—C11—C12	156.70 (13)	N1—P2—C41—C46	−38.07 (14)
C21—P1—C11—C12	−90.72 (14)	C31—P2—C41—C46	85.57 (13)
C16—C11—C12—C13	0.3 (2)	C51—P2—C41—C46	−162.90 (13)
P1—C11—C12—C13	176.66 (14)	N1—P2—C41—C42	141.06 (13)
C11—C12—C13—C14	−0.2 (3)	C31—P2—C41—C42	−95.30 (14)
C12—C13—C14—C15	−0.6 (3)	C51—P2—C41—C42	16.23 (16)
C13—C14—C15—C16	1.2 (3)	C46—C41—C42—C43	0.5 (2)
C14—C15—C16—C11	−1.1 (3)	P2—C41—C42—C43	−178.67 (13)
C12—C11—C16—C15	0.3 (3)	C41—C42—C43—C44	−0.5 (3)
P1—C11—C16—C15	−175.88 (14)	C42—C43—C44—C45	0.0 (3)
O1—P1—C21—C22	−18.58 (16)	C43—C44—C45—C46	0.7 (3)
N1—P1—C21—C22	−151.12 (14)	C44—C45—C46—C41	−0.8 (3)
C11—P1—C21—C22	98.56 (15)	C42—C41—C46—C45	0.2 (2)
O1—P1—C21—C26	164.52 (14)	P2—C41—C46—C45	179.36 (14)
N1—P1—C21—C26	31.99 (17)	N1—P2—C51—C52	155.63 (15)
C11—P1—C21—C26	−78.33 (15)	C41—P2—C51—C52	−84.66 (17)
C26—C21—C22—C23	−0.1 (3)	C31—P2—C51—C52	28.00 (17)
P1—C21—C22—C23	−177.12 (14)	N1—P2—C51—C56	−24.50 (18)
C21—C22—C23—C24	−1.0 (3)	C41—P2—C51—C56	95.21 (15)
C22—C23—C24—C25	1.2 (3)	C31—P2—C51—C56	−152.12 (14)
C23—C24—C25—C26	−0.1 (3)	C56—C51—C52—C53	0.8 (3)
C22—C21—C26—C25	1.2 (3)	P2—C51—C52—C53	−179.31 (16)
P1—C21—C26—C25	178.09 (14)	C51—C52—C53—C54	0.3 (3)
C24—C25—C26—C21	−1.1 (3)	C52—C53—C54—C55	−1.1 (3)
N1—P2—C31—C32	−33.42 (18)	C53—C54—C55—C56	0.9 (3)
C41—P2—C31—C32	−152.60 (15)	C54—C55—C56—C51	0.2 (3)
C51—P2—C31—C32	94.86 (16)	C52—C51—C56—C55	−1.0 (3)
N1—P2—C31—C36	148.99 (15)	P2—C51—C56—C55	179.07 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···O1	0.95	2.34	3.257 (2)	163
C43—H43···O1ⁱ	0.95	2.34	3.257 (2)	162
C45—H45···Cg1ⁱⁱ	0.95	2.92	3.846 (2)	165
C55—H55···Cg2ⁱⁱⁱ	0.95	2.73	3.644 (2)	163

Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) x, y, z+1; (iii) −x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₅NOP₂
M_r	477.45
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	200
a, b, c (Å)	17.6607 (12), 15.1593 (10), 8.9192 (6)
V (Å³)	2387.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.88 × 0.42 × 0.31

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12511, 4498, 4348
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.076, 1.11
No. of reflections	4498
No. of parameters	307
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25
Absolute structure	Flack (1983), 1332 Friedel pairs
Absolute structure parameter	−0.03 (6)

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

P1—N1	1.6014 (13)	P2—N1	1.5532 (13)

P2—N1—P1	146.35 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···O1	0.95	2.34	3.257 (2)	163
C43—H43···O1ⁱ	0.95	2.34	3.257 (2)	162
C45—H45···Cg1ⁱⁱ	0.95	2.92	3.846 (2)	165
C55—H55···Cg2ⁱⁱⁱ	0.95	2.73	3.644 (2)	163

Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) x, y, z+1; (iii) −x, −y, z−1/2.

Acknowledgements

The authors thank Mr Gerhard Schneeberger for helpful discussions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA. Google Scholar
Cameron, A. F., Cameron, I. R. & Keat, R. (1979). Acta Cryst. B35, 1373–1377. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Pages o1028-o1029

doi:10.1107/S1600536811011500

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

Redetermined structure of di­phenyl­phospho­nimidotri­phenyl­phospho­rane: location of the hydrogen atoms and analysis of the inter­molecular inter­actions

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Redetermined structure of diphenylphosphonimidotriphenylphosphorane: location of the hydrogen atoms and analysis of the intermolecular interactions