organic compounds
N,N-Bis(diphenylphosphino)ethylamine
aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa, and bR & D DiVision, Sasol Technology (Pty) Ltd., 1 Klasie Havenga Road, Sasolburg 1947, South Africa
*Correspondence e-mail: cloeten.sci@ufs.ac.za
In the title compound, C26H25NP2, the diphenylphosphino groups are staggered relative to the PNP backbone, even though the ethyl substituent coordinated to the N atom is not sterically bulky. The N atom adapts an almost planar geometry with two P atoms and a C atom of the allyl group attached to it in order to accommodate the steric bulk of the phenyl groups and the alkyl group. The distortion of the trigonal-pyramidal geometry of the nitrogen is further illustrated by the bond angles which range between 114.0 (1) and 123.7 (1)°. There are no classical intermolecular interactions.
Related literature
For similar diphosphineamine non-coordinated ligands with the P—N—P angle ranging between 113.3 (2) and 122.8 (3)°, see: Keat et al. (1981); Cotton et al. (1996); Fei et al. (2003); Cloete et al. (2008).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2005); cell SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SIR97 (Altomare et al., 1999); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536809045978/pv2223sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809045978/pv2223Isup2.hkl
Ethylpropylamine (0.010 mol, 0.45 g) was dissolved in dichloromethane (30 ml) and placed on an ice bath and triethylamine (0.030 mol, 4.22 ml) was added to the solution while being stirred. Chlorodiphenylphosphine (0.020 mol, 3.62 ml) was slowly added to the reaction mixture. The ice bath was removed after 30 minutes and the reaction mixture was allowed to stir at room temperature for a further 12 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. The product was recrystallized from methanol. Single colourless crystals were obtained (yield 2.439 g, 59.0%) the next day which were suitable for X-ray crystallography.The methylene, methyl and aryl H atoms were placed in geometrically idealized positions with distances C—H = 0.99 0.98 and 0.95 Å, respectively and constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C-non-methyl).
Data collection: APEX2 (Bruker, 2005); cell
SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SIR97 (Altomare et al., 1999); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. View of (I) (50% probability displacement ellipsoids). H-atoms were omitted for clarity. | |
Fig. 2. Perspective view of the unit cell of (I) along the a axis. |
C26H25NP2 | F(000) = 872 |
Mr = 413.44 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 5486 reflections |
a = 9.570 (5) Å | θ = 2.6–27.9° |
b = 13.441 (5) Å | µ = 0.21 mm−1 |
c = 16.907 (5) Å | T = 101 K |
β = 91.647 (5)° | Needle, colourless |
V = 2173.9 (15) Å3 | 0.39 × 0.13 × 0.11 mm |
Z = 4 |
Bruker X8 APEXII 4K Kappa CCD diffractometer | 4293 reflections with I > 2σ(I) |
ω and ϕ scans | Rint = 0.046 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 28.3°, θmin = 1.9° |
Tmin = 0.964, Tmax = 0.975 | h = −12→12 |
25117 measured reflections | k = −17→17 |
5401 independent reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0363P)2 + 0.8849P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.43 e Å−3 |
5401 reflections | Δρmin = −0.26 e Å−3 |
262 parameters |
C26H25NP2 | V = 2173.9 (15) Å3 |
Mr = 413.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.570 (5) Å | µ = 0.21 mm−1 |
b = 13.441 (5) Å | T = 101 K |
c = 16.907 (5) Å | 0.39 × 0.13 × 0.11 mm |
β = 91.647 (5)° |
Bruker X8 APEXII 4K Kappa CCD diffractometer | 5401 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 4293 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.975 | Rint = 0.046 |
25117 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.43 e Å−3 |
5401 reflections | Δρmin = −0.26 e Å−3 |
262 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.35096 (13) | 0.21232 (9) | 0.71479 (7) | 0.0155 (3) | |
P1 | 0.41307 (4) | 0.09328 (3) | 0.72417 (2) | 0.01616 (10) | |
P2 | 0.29406 (4) | 0.26318 (3) | 0.62672 (2) | 0.01542 (10) | |
C1 | 0.34840 (16) | 0.28240 (11) | 0.78268 (8) | 0.0177 (3) | |
H1A | 0.3953 | 0.3451 | 0.7678 | 0.021* | |
H1B | 0.402 | 0.2532 | 0.8279 | 0.021* | |
C2 | 0.20138 (17) | 0.30599 (14) | 0.80843 (9) | 0.0250 (4) | |
H2A | 0.2059 | 0.3523 | 0.8532 | 0.037* | |
H2B | 0.1551 | 0.2445 | 0.8245 | 0.037* | |
H2C | 0.1483 | 0.3364 | 0.7643 | 0.037* | |
C11 | 0.32088 (16) | 0.04094 (11) | 0.80923 (9) | 0.0174 (3) | |
C12 | 0.22044 (17) | −0.03189 (12) | 0.79329 (9) | 0.0201 (3) | |
H12 | 0.2041 | −0.0532 | 0.7403 | 0.024* | |
C13 | 0.14338 (17) | −0.07416 (12) | 0.85343 (10) | 0.0230 (3) | |
H13A | 0.0756 | −0.1239 | 0.8413 | 0.028* | |
C14 | 0.16600 (17) | −0.04328 (12) | 0.93092 (9) | 0.0234 (4) | |
H14 | 0.1126 | −0.0708 | 0.972 | 0.028* | |
C15 | 0.26699 (17) | 0.02804 (12) | 0.94820 (9) | 0.0231 (4) | |
H15 | 0.2832 | 0.0488 | 1.0014 | 0.028* | |
C16 | 0.34485 (17) | 0.06956 (12) | 0.88827 (9) | 0.0206 (3) | |
H16 | 0.4147 | 0.1176 | 0.901 | 0.025* | |
C21 | 0.58795 (16) | 0.11232 (11) | 0.76925 (8) | 0.0169 (3) | |
C22 | 0.65088 (16) | 0.03565 (12) | 0.81394 (9) | 0.0193 (3) | |
H22 | 0.5985 | −0.0224 | 0.8252 | 0.023* | |
C23 | 0.78758 (16) | 0.04296 (12) | 0.84186 (9) | 0.0203 (3) | |
H23 | 0.8288 | −0.0104 | 0.8711 | 0.024* | |
C24 | 0.86469 (17) | 0.12790 (13) | 0.82738 (9) | 0.0215 (3) | |
H24 | 0.958 | 0.1337 | 0.8475 | 0.026* | |
C25 | 0.80438 (17) | 0.20455 (12) | 0.78320 (9) | 0.0220 (3) | |
H25 | 0.8568 | 0.263 | 0.7732 | 0.026* | |
C26 | 0.66815 (16) | 0.19654 (12) | 0.75358 (9) | 0.0196 (3) | |
H26 | 0.629 | 0.2488 | 0.7223 | 0.024* | |
C31 | 0.13695 (15) | 0.19368 (11) | 0.59763 (8) | 0.0167 (3) | |
C32 | 0.07951 (17) | 0.20898 (13) | 0.52136 (9) | 0.0222 (3) | |
H32 | 0.1242 | 0.2531 | 0.4862 | 0.027* | |
C33 | −0.04139 (18) | 0.16056 (14) | 0.49693 (10) | 0.0279 (4) | |
H33 | −0.078 | 0.1704 | 0.4447 | 0.034* | |
C34 | −0.10978 (18) | 0.09766 (13) | 0.54801 (10) | 0.0277 (4) | |
H34 | −0.1927 | 0.0642 | 0.5309 | 0.033* | |
C35 | −0.05620 (17) | 0.08398 (13) | 0.62401 (10) | 0.0248 (4) | |
H35 | −0.1032 | 0.0417 | 0.6595 | 0.03* | |
C36 | 0.06593 (16) | 0.13174 (12) | 0.64867 (9) | 0.0196 (3) | |
H36 | 0.1015 | 0.122 | 0.7011 | 0.024* | |
C41 | 0.41629 (16) | 0.21875 (11) | 0.55304 (8) | 0.0161 (3) | |
C42 | 0.52940 (16) | 0.28007 (12) | 0.53709 (9) | 0.0205 (3) | |
H42 | 0.5438 | 0.3394 | 0.5668 | 0.025* | |
C43 | 0.62142 (17) | 0.25524 (13) | 0.47801 (10) | 0.0247 (4) | |
H43 | 0.6984 | 0.2974 | 0.4676 | 0.03* | |
C44 | 0.60062 (17) | 0.16908 (13) | 0.43447 (9) | 0.0234 (4) | |
H44 | 0.6631 | 0.1524 | 0.3939 | 0.028* | |
C45 | 0.48928 (17) | 0.10702 (12) | 0.44978 (9) | 0.0201 (3) | |
H45 | 0.4755 | 0.0477 | 0.42 | 0.024* | |
C46 | 0.39761 (16) | 0.13181 (12) | 0.50904 (9) | 0.0184 (3) | |
H46 | 0.3214 | 0.089 | 0.5196 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0194 (6) | 0.0161 (6) | 0.0110 (6) | 0.0014 (5) | −0.0010 (5) | −0.0018 (5) |
P1 | 0.0210 (2) | 0.01536 (19) | 0.01218 (18) | −0.00001 (16) | 0.00139 (15) | −0.00045 (14) |
P2 | 0.0176 (2) | 0.0164 (2) | 0.01224 (18) | 0.00027 (15) | 0.00057 (15) | −0.00007 (14) |
C1 | 0.0223 (8) | 0.0177 (7) | 0.0130 (7) | 0.0001 (6) | −0.0008 (6) | −0.0030 (6) |
C2 | 0.0246 (9) | 0.0316 (9) | 0.0187 (8) | 0.0050 (7) | 0.0009 (7) | −0.0062 (7) |
C11 | 0.0200 (8) | 0.0170 (7) | 0.0152 (7) | 0.0025 (6) | 0.0012 (6) | 0.0014 (6) |
C12 | 0.0239 (8) | 0.0180 (8) | 0.0185 (7) | 0.0004 (6) | −0.0001 (6) | −0.0010 (6) |
C13 | 0.0209 (8) | 0.0202 (8) | 0.0280 (8) | −0.0029 (7) | 0.0021 (7) | 0.0012 (7) |
C14 | 0.0227 (8) | 0.0242 (8) | 0.0238 (8) | 0.0040 (7) | 0.0080 (7) | 0.0053 (7) |
C15 | 0.0288 (9) | 0.0249 (9) | 0.0159 (7) | 0.0021 (7) | 0.0045 (7) | 0.0009 (6) |
C16 | 0.0245 (8) | 0.0207 (8) | 0.0165 (7) | −0.0019 (7) | 0.0004 (6) | 0.0002 (6) |
C21 | 0.0197 (8) | 0.0190 (7) | 0.0122 (7) | 0.0023 (6) | 0.0042 (6) | −0.0009 (6) |
C22 | 0.0236 (8) | 0.0170 (8) | 0.0176 (7) | 0.0008 (6) | 0.0046 (6) | 0.0004 (6) |
C23 | 0.0226 (8) | 0.0223 (8) | 0.0161 (7) | 0.0062 (7) | 0.0047 (6) | 0.0030 (6) |
C24 | 0.0166 (8) | 0.0264 (8) | 0.0217 (8) | 0.0028 (7) | 0.0031 (6) | 0.0004 (7) |
C25 | 0.0203 (8) | 0.0205 (8) | 0.0254 (8) | −0.0004 (6) | 0.0068 (7) | 0.0029 (7) |
C26 | 0.0211 (8) | 0.0198 (8) | 0.0183 (7) | 0.0037 (6) | 0.0050 (6) | 0.0035 (6) |
C31 | 0.0162 (7) | 0.0191 (7) | 0.0148 (7) | 0.0029 (6) | 0.0003 (6) | −0.0018 (6) |
C32 | 0.0198 (8) | 0.0309 (9) | 0.0159 (7) | 0.0022 (7) | 0.0006 (6) | 0.0031 (6) |
C33 | 0.0218 (9) | 0.0420 (11) | 0.0197 (8) | 0.0015 (8) | −0.0055 (7) | −0.0016 (7) |
C34 | 0.0195 (8) | 0.0311 (10) | 0.0323 (9) | −0.0035 (7) | −0.0039 (7) | −0.0043 (8) |
C35 | 0.0221 (8) | 0.0249 (9) | 0.0274 (9) | −0.0031 (7) | 0.0025 (7) | 0.0013 (7) |
C36 | 0.0184 (8) | 0.0235 (8) | 0.0169 (7) | 0.0018 (6) | −0.0005 (6) | −0.0004 (6) |
C41 | 0.0173 (7) | 0.0195 (7) | 0.0114 (6) | 0.0021 (6) | −0.0006 (6) | 0.0024 (6) |
C42 | 0.0191 (8) | 0.0228 (8) | 0.0193 (7) | −0.0019 (6) | −0.0012 (6) | 0.0011 (6) |
C43 | 0.0180 (8) | 0.0301 (9) | 0.0262 (8) | −0.0014 (7) | 0.0049 (7) | 0.0053 (7) |
C44 | 0.0198 (8) | 0.0344 (10) | 0.0159 (7) | 0.0093 (7) | 0.0031 (6) | 0.0063 (7) |
C45 | 0.0236 (8) | 0.0235 (8) | 0.0132 (7) | 0.0073 (7) | −0.0007 (6) | −0.0007 (6) |
C46 | 0.0186 (8) | 0.0203 (8) | 0.0164 (7) | −0.0002 (6) | 0.0012 (6) | 0.0017 (6) |
N1—C1 | 1.4856 (18) | C23—H23 | 0.95 |
N1—P1 | 1.7127 (14) | C24—C25 | 1.388 (2) |
N1—P2 | 1.7130 (13) | C24—H24 | 0.95 |
P1—C21 | 1.8369 (18) | C25—C26 | 1.387 (2) |
P1—C11 | 1.8478 (15) | C25—H25 | 0.95 |
P2—C31 | 1.8255 (17) | C26—H26 | 0.95 |
P2—C41 | 1.8331 (16) | C31—C36 | 1.391 (2) |
C1—C2 | 1.518 (2) | C31—C32 | 1.402 (2) |
C1—H1A | 0.99 | C32—C33 | 1.380 (2) |
C1—H1B | 0.99 | C32—H32 | 0.95 |
C2—H2A | 0.98 | C33—C34 | 1.386 (2) |
C2—H2B | 0.98 | C33—H33 | 0.95 |
C2—H2C | 0.98 | C34—C35 | 1.382 (2) |
C11—C12 | 1.393 (2) | C34—H34 | 0.95 |
C11—C16 | 1.403 (2) | C35—C36 | 1.387 (2) |
C12—C13 | 1.394 (2) | C35—H35 | 0.95 |
C12—H12 | 0.95 | C36—H36 | 0.95 |
C13—C14 | 1.385 (2) | C41—C42 | 1.393 (2) |
C13—H13A | 0.95 | C41—C46 | 1.394 (2) |
C14—C15 | 1.386 (2) | C42—C43 | 1.391 (2) |
C14—H14 | 0.95 | C42—H42 | 0.95 |
C15—C16 | 1.392 (2) | C43—C44 | 1.384 (2) |
C15—H15 | 0.95 | C43—H43 | 0.95 |
C16—H16 | 0.95 | C44—C45 | 1.383 (2) |
C21—C26 | 1.397 (2) | C44—H44 | 0.95 |
C21—C22 | 1.403 (2) | C45—C46 | 1.391 (2) |
C22—C23 | 1.382 (2) | C45—H45 | 0.95 |
C22—H22 | 0.95 | C46—H46 | 0.95 |
C23—C24 | 1.385 (2) | ||
C1—N1—P1 | 122.29 (10) | C24—C23—H23 | 119.9 |
C1—N1—P2 | 114.00 (10) | C23—C24—C25 | 119.44 (16) |
P1—N1—P2 | 123.65 (7) | C23—C24—H24 | 120.3 |
N1—P1—C21 | 102.58 (7) | C25—C24—H24 | 120.3 |
N1—P1—C11 | 104.81 (7) | C26—C25—C24 | 120.55 (15) |
C21—P1—C11 | 100.36 (7) | C26—C25—H25 | 119.7 |
N1—P2—C31 | 105.59 (7) | C24—C25—H25 | 119.7 |
N1—P2—C41 | 105.52 (7) | C25—C26—C21 | 120.67 (15) |
C31—P2—C41 | 100.78 (7) | C25—C26—H26 | 119.7 |
N1—C1—C2 | 112.95 (13) | C21—C26—H26 | 119.7 |
N1—C1—H1A | 109 | C36—C31—C32 | 118.21 (15) |
C2—C1—H1A | 109 | C36—C31—P2 | 123.55 (12) |
N1—C1—H1B | 109 | C32—C31—P2 | 118.08 (12) |
C2—C1—H1B | 109 | C33—C32—C31 | 120.61 (15) |
H1A—C1—H1B | 107.8 | C33—C32—H32 | 119.7 |
C1—C2—H2A | 109.5 | C31—C32—H32 | 119.7 |
C1—C2—H2B | 109.5 | C32—C33—C34 | 120.51 (16) |
H2A—C2—H2B | 109.5 | C32—C33—H33 | 119.7 |
C1—C2—H2C | 109.5 | C34—C33—H33 | 119.7 |
H2A—C2—H2C | 109.5 | C35—C34—C33 | 119.42 (16) |
H2B—C2—H2C | 109.5 | C35—C34—H34 | 120.3 |
C12—C11—C16 | 118.04 (14) | C33—C34—H34 | 120.3 |
C12—C11—P1 | 117.34 (11) | C34—C35—C36 | 120.32 (15) |
C16—C11—P1 | 124.63 (12) | C34—C35—H35 | 119.8 |
C11—C12—C13 | 121.46 (14) | C36—C35—H35 | 119.8 |
C11—C12—H12 | 119.3 | C35—C36—C31 | 120.88 (15) |
C13—C12—H12 | 119.3 | C35—C36—H36 | 119.6 |
C14—C13—C12 | 119.74 (15) | C31—C36—H36 | 119.6 |
C14—C13—H13A | 120.1 | C42—C41—C46 | 118.76 (14) |
C12—C13—H13A | 120.1 | C42—C41—P2 | 116.96 (12) |
C13—C14—C15 | 119.70 (14) | C46—C41—P2 | 124.14 (12) |
C13—C14—H14 | 120.2 | C43—C42—C41 | 120.57 (15) |
C15—C14—H14 | 120.2 | C43—C42—H42 | 119.7 |
C14—C15—C16 | 120.56 (15) | C41—C42—H42 | 119.7 |
C14—C15—H15 | 119.7 | C44—C43—C42 | 119.90 (15) |
C16—C15—H15 | 119.7 | C44—C43—H43 | 120.1 |
C15—C16—C11 | 120.48 (15) | C42—C43—H43 | 120.1 |
C15—C16—H16 | 119.8 | C45—C44—C43 | 120.33 (14) |
C11—C16—H16 | 119.8 | C45—C44—H44 | 119.8 |
C26—C21—C22 | 117.87 (15) | C43—C44—H44 | 119.8 |
C26—C21—P1 | 122.22 (12) | C44—C45—C46 | 119.69 (15) |
C22—C21—P1 | 119.53 (12) | C44—C45—H45 | 120.2 |
C23—C22—C21 | 121.29 (15) | C46—C45—H45 | 120.2 |
C23—C22—H22 | 119.4 | C45—C46—C41 | 120.75 (14) |
C21—C22—H22 | 119.4 | C45—C46—H46 | 119.6 |
C22—C23—C24 | 120.15 (15) | C41—C46—H46 | 119.6 |
C22—C23—H23 | 119.9 | ||
C1—N1—P1—C21 | −53.54 (12) | C22—C23—C24—C25 | −1.4 (2) |
P2—N1—P1—C21 | 123.41 (9) | C23—C24—C25—C26 | −0.1 (2) |
C1—N1—P1—C11 | 50.91 (13) | C24—C25—C26—C21 | 1.6 (2) |
P2—N1—P1—C11 | −132.13 (9) | C22—C21—C26—C25 | −1.6 (2) |
C1—N1—P2—C31 | −116.42 (11) | P1—C21—C26—C25 | −174.42 (11) |
P1—N1—P2—C31 | 66.40 (10) | N1—P2—C31—C36 | 14.23 (15) |
C1—N1—P2—C41 | 137.38 (10) | C41—P2—C31—C36 | 123.86 (13) |
P1—N1—P2—C41 | −39.80 (11) | N1—P2—C31—C32 | −170.32 (12) |
P1—N1—C1—C2 | −111.26 (14) | C41—P2—C31—C32 | −60.70 (13) |
P2—N1—C1—C2 | 71.52 (15) | C36—C31—C32—C33 | −2.5 (2) |
N1—P1—C11—C12 | 109.42 (13) | P2—C31—C32—C33 | −178.19 (13) |
C21—P1—C11—C12 | −144.47 (12) | C31—C32—C33—C34 | 1.4 (3) |
N1—P1—C11—C16 | −70.44 (15) | C32—C33—C34—C35 | 0.3 (3) |
C21—P1—C11—C16 | 35.67 (15) | C33—C34—C35—C36 | −0.8 (3) |
C16—C11—C12—C13 | 1.3 (2) | C34—C35—C36—C31 | −0.3 (2) |
P1—C11—C12—C13 | −178.59 (12) | C32—C31—C36—C35 | 1.9 (2) |
C11—C12—C13—C14 | 0.3 (2) | P2—C31—C36—C35 | 177.36 (12) |
C12—C13—C14—C15 | −1.2 (2) | N1—P2—C41—C42 | −93.59 (13) |
C13—C14—C15—C16 | 0.6 (2) | C31—P2—C41—C42 | 156.74 (12) |
C14—C15—C16—C11 | 1.0 (2) | N1—P2—C41—C46 | 90.85 (14) |
C12—C11—C16—C15 | −1.9 (2) | C31—P2—C41—C46 | −18.82 (14) |
P1—C11—C16—C15 | 177.98 (12) | C46—C41—C42—C43 | 0.4 (2) |
N1—P1—C21—C26 | −32.09 (13) | P2—C41—C42—C43 | −175.41 (12) |
C11—P1—C21—C26 | −139.97 (12) | C41—C42—C43—C44 | 0.1 (2) |
N1—P1—C21—C22 | 155.21 (11) | C42—C43—C44—C45 | −0.5 (2) |
C11—P1—C21—C22 | 47.33 (13) | C43—C44—C45—C46 | 0.3 (2) |
C26—C21—C22—C23 | 0.2 (2) | C44—C45—C46—C41 | 0.3 (2) |
P1—C21—C22—C23 | 173.18 (11) | C42—C41—C46—C45 | −0.6 (2) |
C21—C22—C23—C24 | 1.3 (2) | P2—C41—C46—C45 | 174.89 (12) |
Experimental details
Crystal data | |
Chemical formula | C26H25NP2 |
Mr | 413.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 101 |
a, b, c (Å) | 9.570 (5), 13.441 (5), 16.907 (5) |
β (°) | 91.647 (5) |
V (Å3) | 2173.9 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.39 × 0.13 × 0.11 |
Data collection | |
Diffractometer | Bruker X8 APEXII 4K Kappa CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.964, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25117, 5401, 4293 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.094, 1.06 |
No. of reflections | 5401 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.26 |
Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXL97 (Sheldrick, 2008), SIR97 (Altomare et al., 1999), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).
Acknowledgements
Financial assistance from the South African National Research Foundation (NRF), the Research Fund of the University of the Free State and SASOL is gratefully acknowledged. Dr A. J. Muller is also gratefully acknowledged for the collection of the crystallographic data. Part of this material is based on work supported by the South African National Research Foundation (GUN 2038915). Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the NRF.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The crystal structure of the title compound, (I), is presented in Figure 1. All bond distances and angles in (I) are normal and fall within the range reported for similar complexes (Keat et al., 1981; Cotton et al., 1996; Fei et al., 2003; Cloete et al., 2008)]. The distance of N1 from the P1—P2—C1 plane is 0.023 (1) Å. The geometry around the phosphorous ligands are distorted from tetrahedral geometry with C—P—C angles being the most distorted (varying from 100.36 (7) to 105.6 (1)°). The P1—N1—P2 angle (123.6 (1)°) is slightly larger than that of other similar compounds quoted above which ranges between 113.3 (2) and 122.8 (3)°. There are no classical intermolecular interactions.
Two conformers are generally found for diphosphineamines and are described (Keat et al., 1981) as C2v and Cs. In C2v conformer, the phosphorous lone pairs are cis with respect to the N—C bond while in the Cs conformer the two lone pairs are trans relative to the N—C bond. It has been postulated (Keat et al., 1981) that the Cs conformer is usually observed for diphoshineamines with relatively bulky substituents on the nitrogen atom. The title compound (I), however has a Cs conformer in solid state even though the ethyl group is not particularly bulky.