Download citation
Download citation
link to html
The mol­ecule of the title compound, C30H34N2O2P2 or Ph2P(O)N(Et)CH2CH2(Et)N(O)PPh2, has crystallographically imposed centrosymmetry. The P-N bond length of 1.656 (2) Å is less than the accepted value for a single P-N bond. The P-O bonds [1.4818 (18) Å] are also short because of double-bond character.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501665X/cf6425sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501665X/cf6425Isup2.hkl
Contains datablock I

CCDC reference: 274356

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.058
  • wR factor = 0.143
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.

N,N'-Bis(ethyldiphenylphosphino)ethylenediamine P,P'-dioxide top
Crystal data top
C30H34N2O2P2F(000) = 548
Mr = 516.53Dx = 1.257 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1657 reflections
a = 10.0697 (13) Åθ = 2.5–20.0°
b = 12.7025 (17) ŵ = 0.19 mm1
c = 10.7016 (14) ÅT = 297 K
β = 94.706 (2)°Block, colourless
V = 1364.2 (3) Å30.17 × 0.14 × 0.14 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
2785 independent reflections
Radiation source: fine-focus sealed tube2254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1212
Tmin = 0.969, Tmax = 0.970k = 1515
10798 measured reflectionsl = 1313
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.056P)2 + 0.5414P]
where P = (Fo2 + 2Fc2)/3
2785 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.23 e Å3
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*/Ueq
C10.9617 (2)0.85968 (19)0.2620 (2)0.0418 (6)
C21.0148 (3)0.9093 (3)0.3698 (3)0.0663 (8)
H20.96840.96420.40370.080*
C31.1360 (3)0.8782 (3)0.4275 (3)0.0770 (10)
H31.17080.91310.49940.092*
C41.2051 (3)0.7973 (3)0.3807 (3)0.0716 (9)
H41.28720.77740.41960.086*
C51.1525 (3)0.7454 (2)0.2756 (3)0.0687 (9)
H51.19830.68900.24410.082*
C61.0322 (3)0.7765 (2)0.2167 (3)0.0578 (7)
H60.99780.74110.14520.069*
C70.7001 (2)0.78923 (19)0.1595 (2)0.0403 (6)
C80.7251 (3)0.7128 (2)0.0715 (3)0.0534 (7)
H80.79510.72200.02110.064*
C90.6474 (3)0.6235 (2)0.0579 (3)0.0655 (8)
H90.66600.57250.00060.079*
C100.5428 (3)0.6100 (3)0.1303 (3)0.0682 (9)
H100.49010.55000.12060.082*
C110.5158 (3)0.6844 (3)0.2169 (3)0.0649 (9)
H110.44500.67460.26620.078*
C120.5930 (2)0.7744 (2)0.2317 (2)0.0495 (6)
H120.57320.82500.29010.059*
C130.9504 (2)1.0198 (2)0.0436 (2)0.0471 (6)
H13A0.99441.02900.12690.057*
H13B0.91631.08770.01450.057*
C140.7339 (3)0.9527 (2)0.0554 (3)0.0567 (7)
H14A0.67190.89500.04870.068*
H14B0.77520.94390.13350.068*
C150.6573 (4)1.0529 (3)0.0620 (4)0.0999 (13)
H15A0.61971.06480.01640.150*
H15B0.58701.04850.12810.150*
H15C0.71561.11010.07860.150*
N10.8384 (2)0.94506 (16)0.04921 (19)0.0441 (5)
O10.74102 (18)0.98013 (14)0.27282 (17)0.0550 (5)
P10.80276 (6)0.90438 (5)0.18962 (6)0.0396 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0450 (14)0.0420 (14)0.0389 (13)0.0067 (11)0.0069 (11)0.0013 (11)
C20.0637 (19)0.073 (2)0.0609 (19)0.0008 (16)0.0013 (15)0.0191 (16)
C30.075 (2)0.092 (3)0.061 (2)0.004 (2)0.0166 (17)0.0148 (18)
C40.0591 (19)0.075 (2)0.078 (2)0.0008 (17)0.0134 (17)0.0140 (18)
C50.0627 (19)0.0552 (18)0.086 (2)0.0108 (15)0.0052 (17)0.0034 (16)
C60.0603 (17)0.0509 (16)0.0606 (18)0.0047 (13)0.0041 (14)0.0097 (14)
C70.0377 (12)0.0400 (13)0.0437 (14)0.0021 (10)0.0055 (10)0.0039 (11)
C80.0519 (16)0.0508 (16)0.0587 (17)0.0092 (13)0.0124 (13)0.0083 (13)
C90.075 (2)0.0500 (17)0.070 (2)0.0105 (15)0.0032 (17)0.0101 (15)
C100.071 (2)0.0611 (19)0.069 (2)0.0303 (16)0.0106 (17)0.0070 (16)
C110.0442 (16)0.085 (2)0.066 (2)0.0185 (15)0.0066 (14)0.0195 (17)
C120.0403 (13)0.0586 (17)0.0503 (15)0.0021 (12)0.0090 (12)0.0052 (13)
C130.0508 (15)0.0450 (15)0.0465 (14)0.0076 (12)0.0092 (11)0.0011 (11)
C140.0518 (16)0.0663 (19)0.0514 (16)0.0098 (14)0.0005 (13)0.0100 (14)
C150.084 (3)0.080 (3)0.130 (4)0.004 (2)0.025 (2)0.020 (2)
N10.0434 (12)0.0472 (12)0.0420 (11)0.0095 (9)0.0058 (9)0.0052 (9)
O10.0651 (12)0.0451 (10)0.0574 (11)0.0022 (9)0.0218 (9)0.0073 (9)
P10.0426 (4)0.0369 (4)0.0406 (4)0.0039 (3)0.0117 (3)0.0020 (3)
Geometric parameters (Å, º) top
C1—C21.383 (4)C10—C111.367 (4)
C1—C61.383 (4)C10—H100.930
C1—P11.811 (3)C11—C121.384 (4)
C2—C31.379 (4)C11—H110.930
C2—H20.930C12—H120.930
C3—C41.360 (5)C13—N11.479 (3)
C3—H30.930C13—C13i1.508 (5)
C4—C51.372 (4)C13—H13A0.970
C4—H40.930C13—H13B0.970
C5—C61.378 (4)C14—N11.476 (3)
C5—H50.930C14—C151.487 (4)
C6—H60.930C14—H14A0.970
C7—C121.389 (3)C14—H14B0.970
C7—C81.391 (3)C15—H15A0.960
C7—P11.805 (2)C15—H15B0.960
C8—C91.378 (4)C15—H15C0.960
C8—H80.930N1—P11.656 (2)
C9—C101.368 (5)O1—P11.4818 (18)
C9—H90.930
C2—C1—C6117.8 (3)C12—C11—H11119.8
C2—C1—P1118.8 (2)C11—C12—C7120.2 (3)
C6—C1—P1123.4 (2)C11—C12—H12119.9
C3—C2—C1120.8 (3)C7—C12—H12119.9
C3—C2—H2119.6N1—C13—C13i111.0 (3)
C1—C2—H2119.6N1—C13—H13A109.4
C4—C3—C2120.8 (3)C13i—C13—H13A109.4
C4—C3—H3119.6N1—C13—H13B109.4
C2—C3—H3119.6C13i—C13—H13B109.4
C3—C4—C5119.4 (3)H13A—C13—H13B108.0
C3—C4—H4120.3N1—C14—C15115.3 (3)
C5—C4—H4120.3N1—C14—H14A108.4
C4—C5—C6120.2 (3)C15—C14—H14A108.4
C4—C5—H5119.9N1—C14—H14B108.4
C6—C5—H5119.9C15—C14—H14B108.4
C5—C6—C1121.1 (3)H14A—C14—H14B107.5
C5—C6—H6119.5C14—C15—H15A109.5
C1—C6—H6119.5C14—C15—H15B109.5
C12—C7—C8118.3 (2)H15A—C15—H15B109.5
C12—C7—P1118.1 (2)C14—C15—H15C109.5
C8—C7—P1123.65 (19)H15A—C15—H15C109.5
C9—C8—C7120.9 (3)H15B—C15—H15C109.5
C9—C8—H8119.6C14—N1—C13115.2 (2)
C7—C8—H8119.6C14—N1—P1121.02 (17)
C10—C9—C8120.0 (3)C13—N1—P1117.37 (16)
C10—C9—H9120.0O1—P1—N1118.38 (11)
C8—C9—H9120.0O1—P1—C7111.77 (11)
C11—C10—C9120.1 (3)N1—P1—C7104.75 (11)
C11—C10—H10119.9O1—P1—C1110.24 (11)
C9—C10—H10119.9N1—P1—C1103.69 (11)
C10—C11—C12120.5 (3)C7—P1—C1107.18 (11)
C10—C11—H11119.8
C6—C1—C2—C31.7 (5)C13i—C13—N1—P1126.8 (3)
P1—C1—C2—C3179.6 (3)C14—N1—P1—O179.3 (2)
C1—C2—C3—C40.8 (5)C13—N1—P1—O171.2 (2)
C2—C3—C4—C50.8 (5)C14—N1—P1—C746.0 (2)
C3—C4—C5—C61.4 (5)C13—N1—P1—C7163.48 (17)
C4—C5—C6—C10.4 (5)C14—N1—P1—C1158.3 (2)
C2—C1—C6—C51.1 (4)C13—N1—P1—C151.2 (2)
P1—C1—C6—C5179.7 (2)C12—C7—P1—O111.6 (2)
C12—C7—C8—C91.3 (4)C8—C7—P1—O1170.9 (2)
P1—C7—C8—C9176.2 (2)C12—C7—P1—N1140.9 (2)
C7—C8—C9—C100.9 (5)C8—C7—P1—N141.5 (2)
C8—C9—C10—C110.5 (5)C12—C7—P1—C1109.3 (2)
C9—C10—C11—C120.4 (5)C8—C7—P1—C168.2 (2)
C10—C11—C12—C70.8 (4)C2—C1—P1—O19.4 (3)
C8—C7—C12—C111.2 (4)C6—C1—P1—O1169.2 (2)
P1—C7—C12—C11176.5 (2)C2—C1—P1—N1118.2 (2)
C15—C14—N1—C1365.6 (3)C6—C1—P1—N163.2 (2)
C15—C14—N1—P185.5 (3)C2—C1—P1—C7131.3 (2)
C13i—C13—N1—C1481.0 (3)C6—C1—P1—C747.3 (2)
Symmetry code: (i) x+2, y+2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds