organic compounds
N,N-Bis(diphenylphosphanyl)cyclopropylamine
aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa
*Correspondence e-mail: EngelbrechtI@ufs.ac.za
In the title compound, C27H25NP2, the diphenylphosphino groups are staggered relative to the PNP backbone. The dihedral angles between the phenyl rings bonded to each P atom are 51.74 (5) and 68.23 (4)°. The coordination around the N atom deviates from trigonal-pyrimidal geometry towards an almost planar arrangement between the N atom and the adjacent P and C atoms; the distance between the N atom and the plane formed by the adjacent C/P/P atoms is 0.098 (2) Å.
Related literature
For similar non-coordinated diphosphineamine ligands with distorted trigonal-pyramidal geometries see: Fei et al. (2003); Keat et al. (1981); Cotton et al. (1996); Cloete et al. (2008, 2009, 2010).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2010); cell SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S1600536810041711/pv2338sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041711/pv2338Isup2.hkl
Cyclopropylamine (0.010 mol, 693 µl) was dissolved in dichloromethane (30 ml) after which the solution was placed on an ice bath. Triethylamine (0.030 mol, 4.21 ml) was added to the solution while stirring. Chlorodiphenylphosphine (0.020 mol, 3.70 ml) was slowly added to the reaction mixture. The ice bath was removed after 1 h and the reaction mixture was allowed to stir at room temperature for a further 13 h. The dichloromethane was removed under reduced pressure. A mixture of hexane (20 ml) and toluene (2 ml) was added to the remaining white powder and was passed through a column containing neutral activated alumina (35 g). The solvent of the
was removed under reduced pressure and the white precipitate was collected. Single colourless crystals suitable for X-ray crystallography were obtained from recrystallization from methanol. (yield: 1.807 g, 43%)The methine, methylene and aromatic H atoms were placed in geometrically idealized positions at C—H = 1.00, 0.99 and 0.95 Å, respectively and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The highest peak is located 0.71 Å from C43 and the deepest hole is situated 0.53 Å from P1.
This structure forms part of ongoing research on ethylene tetramerization. In the title compound, all bond distances and angles are normal and fall within the range for similar complexes (Keat et al., 1981; Cotton et al., 1996; Cloete et al., 2008; 2009; 2010). The distance of N1 from the P1—P2—C1 plane is 0.098 (2) Å showing that the N atom adapts a planar geometry with these atoms in order to accomodate the steric bulk of the phenyl groups. Dihedral angles were calculated based on planes defined by each phenyl ring and the neighboring P atom. The dihedral angles between the various phenyl rings within the molecule are: C1/C2 = 51.74 (5) ° and C3/C4 = 68.23 (4) °. TThe distorted tetrahedral angles of the P atoms range between 100.43 (7) and 105.26 (7) ° which is in good comparison with those in literature. There are no classical intermolecular hydrogen interactions. The title compound is a Cs conformer in the solid state (Keat et al., 1981) in which the phosphorous lone pairs are trans with respect to the N–C bond.
For similar non-coordinated diphosphineamine ligands with distorted trigonal-pyramidal geometries see: Keat et al. (1981); Cotton et al. (1996); Cloete et al. (2008, 2009, 2010). For [please specify], see: Fei et al. (2003).
Data collection: APEX2 (Bruker, 2010); cell
SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity. |
C27H25NP2 | F(000) = 896 |
Mr = 425.42 | Dx = 1.254 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 8432 reflections |
a = 14.460 (4) Å | θ = 2.5–27.5° |
b = 10.486 (5) Å | µ = 0.21 mm−1 |
c = 17.053 (5) Å | T = 100 K |
β = 119.358 (5)° | Cuboid, colourless |
V = 2253.6 (15) Å3 | 0.33 × 0.18 × 0.16 mm |
Z = 4 |
Bruker X8 APEXII 4K Kappa CCD diffractometer | 5581 independent reflections |
Radiation source: fine-focus sealed tube | 4477 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.041 |
ω and φ scans | θmax = 28.4°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −18→19 |
Tmin = 0.935, Tmax = 0.968 | k = −10→13 |
33310 measured reflections | l = −22→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0466P)2 + 1.0215P] where P = (Fo2 + 2Fc2)/3 |
5581 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C27H25NP2 | V = 2253.6 (15) Å3 |
Mr = 425.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.460 (4) Å | µ = 0.21 mm−1 |
b = 10.486 (5) Å | T = 100 K |
c = 17.053 (5) Å | 0.33 × 0.18 × 0.16 mm |
β = 119.358 (5)° |
Bruker X8 APEXII 4K Kappa CCD diffractometer | 5581 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 4477 reflections with I > 2.0σ(I) |
Tmin = 0.935, Tmax = 0.968 | Rint = 0.041 |
33310 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.33 e Å−3 |
5581 reflections | Δρmin = −0.36 e Å−3 |
271 parameters |
Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 10 s/frame. A total of 1407 frames were collected with a frame width of 0.5° covering up to θ = 28.36° with 99.3% completeness accomplished. Spectroscopy data: 1H NMR (300 MHz, CD2Cl2): δ = 0.3 to 0.7 (m, 4H, 2 x CH2), 2.6 (m, 1H, CH), 7.3 to 7.5 (m, 20H, Ar); 31P NMR (121 MHz, CD2Cl2): δ = 63.4 (s). |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.59558 (12) | 0.25225 (15) | 0.55966 (10) | 0.0209 (3) | |
H1 | 0.5473 | 0.1995 | 0.5729 | 0.025* | |
C2 | 0.54277 (14) | 0.32353 (16) | 0.47190 (11) | 0.0267 (4) | |
H2A | 0.4654 | 0.3121 | 0.4327 | 0.032* | |
H2B | 0.5833 | 0.3354 | 0.4396 | 0.032* | |
C3 | 0.58012 (14) | 0.39375 (16) | 0.55920 (11) | 0.0274 (4) | |
H3A | 0.6436 | 0.4488 | 0.5804 | 0.033* | |
H3B | 0.5256 | 0.4255 | 0.5735 | 0.033* | |
C11 | 0.71357 (12) | 0.07960 (14) | 0.74371 (10) | 0.0184 (3) | |
C12 | 0.63529 (12) | −0.00544 (14) | 0.68578 (11) | 0.0211 (3) | |
H12 | 0.6151 | −0.0062 | 0.6237 | 0.025* | |
C13 | 0.58661 (13) | −0.08882 (16) | 0.71768 (11) | 0.0248 (3) | |
H13 | 0.5327 | −0.145 | 0.6773 | 0.03* | |
C14 | 0.61675 (14) | −0.08999 (16) | 0.80836 (12) | 0.0258 (4) | |
H14 | 0.5834 | −0.1467 | 0.8303 | 0.031* | |
C15 | 0.69601 (13) | −0.00792 (15) | 0.86719 (11) | 0.0245 (3) | |
H15 | 0.7173 | −0.0093 | 0.9295 | 0.029* | |
C16 | 0.74413 (13) | 0.07601 (15) | 0.83527 (11) | 0.0213 (3) | |
H16 | 0.7984 | 0.1316 | 0.876 | 0.026* | |
C21 | 0.77084 (12) | 0.33887 (14) | 0.75153 (10) | 0.0180 (3) | |
C22 | 0.68675 (13) | 0.37085 (15) | 0.76614 (10) | 0.0205 (3) | |
H22 | 0.635 | 0.3084 | 0.7576 | 0.025* | |
C23 | 0.67822 (14) | 0.49346 (15) | 0.79308 (11) | 0.0251 (3) | |
H23 | 0.6203 | 0.5145 | 0.8022 | 0.03* | |
C24 | 0.75390 (14) | 0.58542 (16) | 0.80678 (11) | 0.0258 (4) | |
H24 | 0.7471 | 0.6694 | 0.8242 | 0.031* | |
C25 | 0.83918 (14) | 0.55410 (15) | 0.79498 (11) | 0.0241 (3) | |
H25 | 0.8921 | 0.616 | 0.8057 | 0.029* | |
C26 | 0.84747 (13) | 0.43169 (15) | 0.76732 (10) | 0.0207 (3) | |
H26 | 0.9061 | 0.4109 | 0.7591 | 0.025* | |
C31 | 0.76517 (12) | −0.03248 (14) | 0.55113 (10) | 0.0182 (3) | |
C32 | 0.68867 (13) | −0.12527 (15) | 0.50250 (11) | 0.0222 (3) | |
H32 | 0.6234 | −0.1006 | 0.4519 | 0.027* | |
C33 | 0.70678 (14) | −0.25267 (15) | 0.52714 (11) | 0.0262 (4) | |
H33 | 0.654 | −0.3147 | 0.4938 | 0.031* | |
C34 | 0.80162 (14) | −0.28923 (15) | 0.60026 (12) | 0.0272 (4) | |
H34 | 0.8142 | −0.3766 | 0.6168 | 0.033* | |
C35 | 0.87866 (14) | −0.19906 (15) | 0.64963 (12) | 0.0269 (4) | |
H35 | 0.9436 | −0.2245 | 0.7002 | 0.032* | |
C36 | 0.86059 (13) | −0.07105 (15) | 0.62481 (11) | 0.0223 (3) | |
H36 | 0.9137 | −0.0095 | 0.6583 | 0.027* | |
C41 | 0.85308 (12) | 0.20398 (14) | 0.53650 (10) | 0.0173 (3) | |
C42 | 0.91036 (12) | 0.14796 (15) | 0.49881 (10) | 0.0201 (3) | |
H42 | 0.8889 | 0.0675 | 0.4699 | 0.024* | |
C43 | 0.99796 (13) | 0.20875 (16) | 0.50336 (11) | 0.0239 (3) | |
H43 | 1.0358 | 0.1699 | 0.4772 | 0.029* | |
C44 | 1.03073 (13) | 0.32609 (16) | 0.54587 (12) | 0.0267 (4) | |
H44 | 1.0911 | 0.3672 | 0.5492 | 0.032* | |
C45 | 0.97516 (14) | 0.38290 (15) | 0.58346 (12) | 0.0266 (4) | |
H45 | 0.9978 | 0.4628 | 0.6131 | 0.032* | |
C46 | 0.88620 (13) | 0.32314 (14) | 0.57785 (11) | 0.0222 (3) | |
H46 | 0.8474 | 0.3638 | 0.6024 | 0.027* | |
N1 | 0.70166 (10) | 0.20116 (11) | 0.59277 (8) | 0.0171 (3) | |
P1 | 0.78650 (3) | 0.18492 (4) | 0.70717 (3) | 0.01690 (10) | |
P2 | 0.72688 (3) | 0.13260 (4) | 0.51349 (3) | 0.01718 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0195 (7) | 0.0222 (8) | 0.0204 (8) | 0.0035 (6) | 0.0094 (6) | −0.0003 (6) |
C2 | 0.0286 (9) | 0.0274 (8) | 0.0215 (8) | 0.0078 (7) | 0.0101 (7) | 0.0011 (7) |
C3 | 0.0304 (9) | 0.0247 (8) | 0.0227 (8) | 0.0083 (7) | 0.0097 (7) | 0.0006 (7) |
C11 | 0.0196 (7) | 0.0158 (7) | 0.0213 (8) | 0.0023 (6) | 0.0112 (6) | 0.0005 (6) |
C12 | 0.0254 (8) | 0.0202 (7) | 0.0193 (8) | −0.0002 (6) | 0.0124 (7) | −0.0017 (6) |
C13 | 0.0272 (9) | 0.0216 (8) | 0.0261 (9) | −0.0058 (6) | 0.0135 (7) | −0.0045 (7) |
C14 | 0.0304 (9) | 0.0222 (8) | 0.0306 (9) | −0.0029 (7) | 0.0194 (8) | 0.0013 (7) |
C15 | 0.0301 (9) | 0.0257 (8) | 0.0203 (8) | 0.0007 (7) | 0.0142 (7) | 0.0019 (6) |
C16 | 0.0227 (8) | 0.0202 (7) | 0.0196 (8) | −0.0014 (6) | 0.0092 (6) | −0.0003 (6) |
C21 | 0.0208 (8) | 0.0186 (7) | 0.0134 (7) | 0.0010 (6) | 0.0073 (6) | 0.0002 (6) |
C22 | 0.0220 (8) | 0.0209 (7) | 0.0187 (8) | −0.0005 (6) | 0.0102 (6) | −0.0007 (6) |
C23 | 0.0283 (9) | 0.0251 (8) | 0.0244 (8) | 0.0051 (7) | 0.0148 (7) | −0.0007 (7) |
C24 | 0.0362 (9) | 0.0186 (7) | 0.0209 (8) | 0.0025 (7) | 0.0127 (7) | −0.0009 (6) |
C25 | 0.0315 (9) | 0.0206 (8) | 0.0186 (8) | −0.0048 (7) | 0.0112 (7) | −0.0011 (6) |
C26 | 0.0227 (8) | 0.0229 (8) | 0.0165 (7) | −0.0022 (6) | 0.0097 (6) | −0.0011 (6) |
C31 | 0.0225 (8) | 0.0173 (7) | 0.0216 (8) | −0.0009 (6) | 0.0161 (7) | −0.0015 (6) |
C32 | 0.0253 (8) | 0.0222 (8) | 0.0232 (8) | −0.0029 (6) | 0.0150 (7) | −0.0034 (6) |
C33 | 0.0365 (10) | 0.0211 (8) | 0.0279 (9) | −0.0086 (7) | 0.0210 (8) | −0.0066 (7) |
C34 | 0.0413 (10) | 0.0162 (7) | 0.0311 (9) | −0.0017 (7) | 0.0233 (8) | 0.0003 (7) |
C35 | 0.0289 (9) | 0.0238 (8) | 0.0286 (9) | 0.0024 (7) | 0.0146 (7) | 0.0052 (7) |
C36 | 0.0226 (8) | 0.0192 (7) | 0.0270 (8) | −0.0018 (6) | 0.0136 (7) | −0.0008 (6) |
C41 | 0.0200 (7) | 0.0178 (7) | 0.0147 (7) | 0.0011 (6) | 0.0088 (6) | 0.0038 (6) |
C42 | 0.0241 (8) | 0.0178 (7) | 0.0198 (8) | 0.0027 (6) | 0.0118 (7) | 0.0018 (6) |
C43 | 0.0246 (8) | 0.0263 (8) | 0.0264 (8) | 0.0054 (6) | 0.0169 (7) | 0.0078 (7) |
C44 | 0.0248 (8) | 0.0280 (8) | 0.0291 (9) | −0.0039 (7) | 0.0147 (7) | 0.0077 (7) |
C45 | 0.0343 (9) | 0.0196 (8) | 0.0255 (9) | −0.0068 (7) | 0.0143 (8) | 0.0001 (6) |
C46 | 0.0308 (9) | 0.0178 (7) | 0.0224 (8) | −0.0005 (6) | 0.0164 (7) | 0.0010 (6) |
N1 | 0.0179 (6) | 0.0186 (6) | 0.0155 (6) | 0.0020 (5) | 0.0088 (5) | −0.0004 (5) |
P1 | 0.0173 (2) | 0.01718 (19) | 0.0168 (2) | 0.00046 (14) | 0.00886 (16) | −0.00058 (14) |
P2 | 0.0189 (2) | 0.01685 (19) | 0.0170 (2) | 0.00047 (14) | 0.00976 (16) | −0.00097 (14) |
C1—N1 | 1.452 (2) | C25—C26 | 1.393 (2) |
C1—C3 | 1.500 (2) | C25—H25 | 0.95 |
C1—C2 | 1.504 (2) | C26—H26 | 0.95 |
C1—H1 | 1 | C31—C36 | 1.395 (2) |
C2—C3 | 1.504 (2) | C31—C32 | 1.399 (2) |
C2—H2A | 0.99 | C31—P2 | 1.8349 (17) |
C2—H2B | 0.99 | C32—C33 | 1.386 (2) |
C3—H3A | 0.99 | C32—H32 | 0.95 |
C3—H3B | 0.99 | C33—C34 | 1.380 (3) |
C11—C12 | 1.399 (2) | C33—H33 | 0.95 |
C11—C16 | 1.399 (2) | C34—C35 | 1.387 (2) |
C11—P1 | 1.8342 (16) | C34—H34 | 0.95 |
C12—C13 | 1.390 (2) | C35—C36 | 1.393 (2) |
C12—H12 | 0.95 | C35—H35 | 0.95 |
C13—C14 | 1.386 (2) | C36—H36 | 0.95 |
C13—H13 | 0.95 | C41—C46 | 1.399 (2) |
C14—C15 | 1.390 (2) | C41—C42 | 1.402 (2) |
C14—H14 | 0.95 | C41—P2 | 1.8282 (16) |
C15—C16 | 1.388 (2) | C42—C43 | 1.386 (2) |
C15—H15 | 0.95 | C42—H42 | 0.95 |
C16—H16 | 0.95 | C43—C44 | 1.388 (2) |
C21—C22 | 1.396 (2) | C43—H43 | 0.95 |
C21—C26 | 1.398 (2) | C44—C45 | 1.384 (2) |
C21—P1 | 1.8433 (17) | C44—H44 | 0.95 |
C22—C23 | 1.391 (2) | C45—C46 | 1.391 (2) |
C22—H22 | 0.95 | C45—H45 | 0.95 |
C23—C24 | 1.390 (2) | C46—H46 | 0.95 |
C23—H23 | 0.95 | N1—P2 | 1.7208 (13) |
C24—C25 | 1.383 (2) | N1—P1 | 1.7301 (14) |
C24—H24 | 0.95 | ||
N1—C1—C3 | 119.55 (14) | C26—C25—H25 | 120 |
N1—C1—C2 | 119.64 (14) | C25—C26—C21 | 121.00 (15) |
C3—C1—C2 | 60.09 (11) | C25—C26—H26 | 119.5 |
N1—C1—H1 | 115.5 | C21—C26—H26 | 119.5 |
C3—C1—H1 | 115.5 | C36—C31—C32 | 118.53 (14) |
C2—C1—H1 | 115.5 | C36—C31—P2 | 125.74 (12) |
C1—C2—C3 | 59.83 (11) | C32—C31—P2 | 115.68 (12) |
C1—C2—H2A | 117.8 | C33—C32—C31 | 120.89 (16) |
C3—C2—H2A | 117.8 | C33—C32—H32 | 119.6 |
C1—C2—H2B | 117.8 | C31—C32—H32 | 119.6 |
C3—C2—H2B | 117.8 | C34—C33—C32 | 119.85 (15) |
H2A—C2—H2B | 114.9 | C34—C33—H33 | 120.1 |
C1—C3—C2 | 60.07 (11) | C32—C33—H33 | 120.1 |
C1—C3—H3A | 117.8 | C33—C34—C35 | 120.37 (15) |
C2—C3—H3A | 117.8 | C33—C34—H34 | 119.8 |
C1—C3—H3B | 117.8 | C35—C34—H34 | 119.8 |
C2—C3—H3B | 117.8 | C34—C35—C36 | 119.81 (16) |
H3A—C3—H3B | 114.9 | C34—C35—H35 | 120.1 |
C12—C11—C16 | 118.33 (14) | C36—C35—H35 | 120.1 |
C12—C11—P1 | 123.02 (12) | C35—C36—C31 | 120.55 (15) |
C16—C11—P1 | 118.40 (12) | C35—C36—H36 | 119.7 |
C13—C12—C11 | 120.96 (15) | C31—C36—H36 | 119.7 |
C13—C12—H12 | 119.5 | C46—C41—C42 | 118.17 (14) |
C11—C12—H12 | 119.5 | C46—C41—P2 | 122.20 (12) |
C14—C13—C12 | 119.98 (15) | C42—C41—P2 | 118.81 (12) |
C14—C13—H13 | 120 | C43—C42—C41 | 120.72 (15) |
C12—C13—H13 | 120 | C43—C42—H42 | 119.6 |
C13—C14—C15 | 119.78 (15) | C41—C42—H42 | 119.6 |
C13—C14—H14 | 120.1 | C42—C43—C44 | 120.36 (15) |
C15—C14—H14 | 120.1 | C42—C43—H43 | 119.8 |
C16—C15—C14 | 120.26 (15) | C44—C43—H43 | 119.8 |
C16—C15—H15 | 119.9 | C45—C44—C43 | 119.75 (15) |
C14—C15—H15 | 119.9 | C45—C44—H44 | 120.1 |
C15—C16—C11 | 120.65 (15) | C43—C44—H44 | 120.1 |
C15—C16—H16 | 119.7 | C44—C45—C46 | 120.09 (15) |
C11—C16—H16 | 119.7 | C44—C45—H45 | 120 |
C22—C21—C26 | 118.40 (14) | C46—C45—H45 | 120 |
C22—C21—P1 | 125.20 (12) | C45—C46—C41 | 120.89 (15) |
C26—C21—P1 | 116.33 (12) | C45—C46—H46 | 119.6 |
C23—C22—C21 | 120.45 (15) | C41—C46—H46 | 119.6 |
C23—C22—H22 | 119.8 | C1—N1—P2 | 116.03 (10) |
C21—C22—H22 | 119.8 | C1—N1—P1 | 120.30 (10) |
C24—C23—C22 | 120.45 (16) | P2—N1—P1 | 122.58 (8) |
C24—C23—H23 | 119.8 | N1—P1—C11 | 103.56 (7) |
C22—C23—H23 | 119.8 | N1—P1—C21 | 102.40 (7) |
C25—C24—C23 | 119.71 (15) | C11—P1—C21 | 100.43 (7) |
C25—C24—H24 | 120.1 | N1—P2—C41 | 103.54 (7) |
C23—C24—H24 | 120.1 | N1—P2—C31 | 105.26 (7) |
C24—C25—C26 | 119.94 (15) | C41—P2—C31 | 102.29 (7) |
C24—C25—H25 | 120 | ||
N1—C1—C2—C3 | −109.10 (16) | C44—C45—C46—C41 | 1.6 (2) |
N1—C1—C3—C2 | 109.25 (16) | C42—C41—C46—C45 | −1.6 (2) |
C16—C11—C12—C13 | 2.0 (2) | P2—C41—C46—C45 | −171.14 (12) |
P1—C11—C12—C13 | 176.10 (12) | C3—C1—N1—P2 | −111.08 (14) |
C11—C12—C13—C14 | −1.1 (2) | C2—C1—N1—P2 | −40.77 (18) |
C12—C13—C14—C15 | −0.3 (3) | C3—C1—N1—P1 | 80.49 (16) |
C13—C14—C15—C16 | 0.7 (3) | C2—C1—N1—P1 | 150.80 (12) |
C14—C15—C16—C11 | 0.2 (2) | C1—N1—P1—C11 | 58.57 (13) |
C12—C11—C16—C15 | −1.5 (2) | P2—N1—P1—C11 | −109.08 (9) |
P1—C11—C16—C15 | −175.91 (12) | C1—N1—P1—C21 | −45.54 (13) |
C26—C21—C22—C23 | 1.9 (2) | P2—N1—P1—C21 | 146.81 (9) |
P1—C21—C22—C23 | −174.81 (12) | C12—C11—P1—N1 | 24.39 (14) |
C21—C22—C23—C24 | −0.7 (2) | C16—C11—P1—N1 | −161.48 (12) |
C22—C23—C24—C25 | −1.1 (2) | C12—C11—P1—C21 | 129.99 (13) |
C23—C24—C25—C26 | 1.6 (2) | C16—C11—P1—C21 | −55.87 (13) |
C24—C25—C26—C21 | −0.3 (2) | C22—C21—P1—N1 | 79.58 (14) |
C22—C21—C26—C25 | −1.4 (2) | C26—C21—P1—N1 | −97.23 (12) |
P1—C21—C26—C25 | 175.60 (12) | C22—C21—P1—C11 | −26.95 (15) |
C36—C31—C32—C33 | 0.4 (2) | C26—C21—P1—C11 | 156.23 (12) |
P2—C31—C32—C33 | −177.16 (12) | C1—N1—P2—C41 | 131.82 (11) |
C31—C32—C33—C34 | −0.4 (2) | P1—N1—P2—C41 | −60.04 (10) |
C32—C33—C34—C35 | 0.5 (3) | C1—N1—P2—C31 | −121.16 (11) |
C33—C34—C35—C36 | −0.6 (3) | P1—N1—P2—C31 | 46.98 (10) |
C34—C35—C36—C31 | 0.6 (2) | C46—C41—P2—N1 | −25.59 (14) |
C32—C31—C36—C35 | −0.5 (2) | C42—C41—P2—N1 | 164.95 (12) |
P2—C31—C36—C35 | 176.77 (12) | C46—C41—P2—C31 | −134.83 (13) |
C46—C41—C42—C43 | 0.6 (2) | C42—C41—P2—C31 | 55.71 (13) |
P2—C41—C42—C43 | 170.51 (12) | C36—C31—P2—N1 | −71.90 (15) |
C41—C42—C43—C44 | 0.4 (2) | C32—C31—P2—N1 | 105.44 (12) |
C42—C43—C44—C45 | −0.4 (2) | C36—C31—P2—C41 | 36.03 (15) |
C43—C44—C45—C46 | −0.6 (3) | C32—C31—P2—C41 | −146.64 (12) |
Experimental details
Crystal data | |
Chemical formula | C27H25NP2 |
Mr | 425.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 14.460 (4), 10.486 (5), 17.053 (5) |
β (°) | 119.358 (5) |
V (Å3) | 2253.6 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.33 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker X8 APEXII 4K Kappa CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.935, 0.968 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 33310, 5581, 4477 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.105, 1.06 |
No. of reflections | 5581 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.36 |
Computer programs: APEX2 (Bruker, 2010), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).
Acknowledgements
Financial assistance from the Department of Science and Technology (DST) of South Africa, the South African National Research Foundation (NRF), as well as the DST–NRF centre of excellence (c*change) and the University of the Free State are gratefully acknowledged.
References
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This structure forms part of ongoing research on ethylene tetramerization. In the title compound, all bond distances and angles are normal and fall within the range for similar complexes (Keat et al., 1981; Cotton et al., 1996; Cloete et al., 2008; 2009; 2010). The distance of N1 from the P1—P2—C1 plane is 0.098 (2) Å showing that the N atom adapts a planar geometry with these atoms in order to accomodate the steric bulk of the phenyl groups. Dihedral angles were calculated based on planes defined by each phenyl ring and the neighboring P atom. The dihedral angles between the various phenyl rings within the molecule are: C1/C2 = 51.74 (5) ° and C3/C4 = 68.23 (4) °. TThe distorted tetrahedral angles of the P atoms range between 100.43 (7) and 105.26 (7) ° which is in good comparison with those in literature. There are no classical intermolecular hydrogen interactions. The title compound is a Cs conformer in the solid state (Keat et al., 1981) in which the phosphorous lone pairs are trans with respect to the N–C bond.