[2-(4-Methyl-piperazin-1-ylmeth-yl)phen-yl]diphenyl-phosphane.

In the title compound, C(24)H(27)N(2)P, the P atom is bonded to three C atoms in a trigonal-pyramidal geometry. The overall Ψ-trigonal-bipyramidal coordination of the P atom is established when the contribution of the electron lone pair and of the N-P donor-acceptor distance of 3.051 (3)Å are considered. The 4-methyl-piperazinyl ring adopts a chair conformation. Intra- and inter-molecular C-H⋯π hydrogen bonding leads to the consolidation of the structure.

Related literature

For organophospho­rus compounds containing substituents with the capability of intra­molecular class="Species">donor⋯acceclass="Chemical">ptor inter­actions, see: Alberico et al. (2007 ▶); Chandrasekaran et al. (2002 ▶); Chuit et al. (1993 ▶); class="Chemical">pan class="Chemical">Pretorius et al. (2004 ▶). For the structures of triclinic polymorphs of triphenyl­phosphine, see: Ziemer et al. (2000 ▶).

Experimental

Crystal data

pan class="Chemical">C24H27N2P

M = 374.45

Monoclinic,

a = 9.3689 (10) Å

b = 14.6735 (16) Å

c = 15.4362 (16) Å

β = 100.849 (2)°

V = 2084.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 297 K

0.30 × 0.26 × 0.21 mm

Data collection

Bruker SMART pan class="Gene">APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.959, T max = 0.971

14906 measured reflections

3667 independent reflections

2811 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.178

S = 1.20

3667 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refineclass="Species">ment: SAINT-class="Chemical">pan class="Chemical">Plus (Bruker, 2001 ▶); 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, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049526/wm2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049526/wm2285Isup2.hkl

Additional supplepan class="Species">mentary materials: crystallograclass="Chemical">phic information; 3D view; checkCIF reclass="Chemical">port

C24H27N2P	F(000) = 800
Mr = 374.45	Dx = 1.193 Mg m−3
Monoclinic, P21/n	Melting point: 342 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.3689 (10) Å	Cell parameters from 3207 reflections
b = 14.6735 (16) Å	θ = 2.4–23.9°
c = 15.4362 (16) Å	µ = 0.14 mm−1
β = 100.849 (2)°	T = 297 K
V = 2084.2 (4) Å3	Block, colourless
Z = 4	0.30 × 0.26 × 0.21 mm

Bruker SMART APEX CCD area-detector diffractometer	3667 independent reflections
Radiation source: fine-focus sealed tube	2811 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 25°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.959, Tmax = 0.971	k = −17→17
14906 measured reflections	l = −18→18

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0598P)2 + 1.2183P] where P = (Fo2 + 2Fc2)/3
3667 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6682 (4)	0.5851 (2)	0.1668 (3)	0.0428 (9)
C2	0.5236 (4)	0.6120 (2)	0.1377 (3)	0.0486 (10)
C3	0.4311 (5)	0.6148 (3)	0.1980 (4)	0.0666 (13)
H3	0.3349	0.6325	0.1794	0.08*
C4	0.4792 (6)	0.5920 (3)	0.2845 (4)	0.0783 (16)
H4	0.4153	0.5936	0.3239	0.094*
C5	0.6207 (6)	0.5670 (3)	0.3133 (3)	0.0731 (14)
H5	0.6535	0.5525	0.3724	0.088*
C6	0.7139 (5)	0.5633 (3)	0.2549 (3)	0.0542 (11)
H6	0.8099	0.5459	0.2749	0.065*
C7	0.4705 (4)	0.6395 (3)	0.0433 (3)	0.0541 (11)
H7A	0.4805	0.5884	0.0049	0.065*
H7B	0.3683	0.6554	0.0348	0.065*
C8	0.5243 (4)	0.7993 (2)	0.0655 (3)	0.0516 (10)
H8A	0.5466	0.7889	0.1287	0.062*
H8B	0.4223	0.8152	0.0494	0.062*
C9	0.6161 (4)	0.8769 (2)	0.0421 (3)	0.0493 (10)
H9A	0.5953	0.9316	0.0726	0.059*
H9B	0.7181	0.8623	0.0615	0.059*
C10	0.6156 (5)	0.8106 (3)	−0.0969 (3)	0.0603 (12)
H10A	0.7175	0.7946	−0.0799	0.072*
H10B	0.5951	0.8207	−0.1602	0.072*
C11	0.5246 (5)	0.7335 (3)	−0.0750 (3)	0.0610 (12)
H11A	0.4226	0.7479	−0.0948	0.073*
H11B	0.5463	0.679	−0.1055	0.073*
C12	0.6772 (5)	0.9677 (3)	−0.0734 (3)	0.0725 (14)
H12A	0.6606	1.021	−0.0406	0.109*
H12B	0.6525	0.9807	−0.1354	0.109*
H12C	0.7777	0.9507	−0.0584	0.109*
C13	0.8981 (4)	0.6775 (2)	0.1019 (2)	0.0374 (9)
C14	0.9778 (4)	0.6993 (3)	0.0381 (3)	0.0526 (10)
H14	0.9738	0.6612	−0.0105	0.063*
C15	1.0624 (5)	0.7758 (3)	0.0448 (3)	0.0672 (13)
H15	1.1167	0.7885	0.0016	0.081*
C16	1.0676 (5)	0.8335 (3)	0.1143 (3)	0.0666 (13)
H16	1.1241	0.886	0.1183	0.08*
C17	0.9895 (5)	0.8137 (3)	0.1778 (3)	0.0626 (12)
H17	0.9931	0.853	0.2255	0.075*
C18	0.9055 (4)	0.7367 (3)	0.1725 (3)	0.0485 (10)
H18	0.8532	0.7241	0.2167	0.058*
C19	0.9139 (4)	0.4871 (2)	0.1368 (2)	0.0400 (9)
C20	1.0627 (4)	0.4962 (3)	0.1523 (3)	0.0554 (11)
H20	1.1033	0.5516	0.1405	0.066*
C21	1.1529 (5)	0.4251 (3)	0.1850 (3)	0.0639 (12)
H21	1.2532	0.4328	0.1942	0.077*
C22	1.0960 (5)	0.3439 (3)	0.2037 (3)	0.0582 (11)
H22	1.157	0.2964	0.2269	0.07*
C23	0.9485 (5)	0.3325 (3)	0.1881 (3)	0.0546 (11)
H23	0.9091	0.2769	0.2004	0.065*
C24	0.8585 (4)	0.4026 (2)	0.1544 (2)	0.0461 (10)
H24	0.7585	0.3935	0.143	0.055*
N1	0.5526 (3)	0.7170 (2)	0.0195 (2)	0.0432 (8)
N2	0.5876 (4)	0.8936 (2)	−0.0522 (2)	0.0534 (9)
P1	0.78585 (10)	0.57472 (7)	0.08427 (6)	0.0391 (3)

	U11	U22	U33	U12	U13	U23
C1	0.044 (2)	0.032 (2)	0.054 (2)	−0.0038 (17)	0.0124 (18)	0.0048 (17)
C2	0.041 (2)	0.032 (2)	0.075 (3)	−0.0081 (17)	0.017 (2)	−0.0027 (19)
C3	0.053 (3)	0.046 (3)	0.109 (4)	−0.011 (2)	0.037 (3)	0.001 (3)
C4	0.101 (4)	0.046 (3)	0.109 (5)	−0.006 (3)	0.073 (4)	0.006 (3)
C5	0.109 (4)	0.048 (3)	0.072 (3)	0.010 (3)	0.043 (3)	0.013 (2)
C6	0.069 (3)	0.044 (2)	0.055 (3)	0.009 (2)	0.025 (2)	0.007 (2)
C7	0.037 (2)	0.044 (2)	0.075 (3)	−0.0056 (18)	−0.007 (2)	−0.005 (2)
C8	0.056 (3)	0.041 (2)	0.059 (3)	0.0023 (19)	0.014 (2)	−0.0035 (19)
C9	0.049 (2)	0.036 (2)	0.062 (3)	−0.0010 (18)	0.010 (2)	−0.0048 (19)
C10	0.071 (3)	0.064 (3)	0.045 (2)	−0.002 (2)	0.008 (2)	0.001 (2)
C11	0.065 (3)	0.056 (3)	0.054 (3)	0.001 (2)	−0.007 (2)	−0.009 (2)
C12	0.072 (3)	0.059 (3)	0.091 (4)	0.003 (2)	0.029 (3)	0.021 (3)
C13	0.034 (2)	0.037 (2)	0.039 (2)	0.0023 (16)	0.0011 (16)	0.0081 (17)
C14	0.050 (2)	0.054 (3)	0.054 (2)	−0.002 (2)	0.011 (2)	0.004 (2)
C15	0.059 (3)	0.070 (3)	0.076 (3)	−0.015 (2)	0.022 (3)	0.018 (3)
C16	0.055 (3)	0.056 (3)	0.082 (3)	−0.019 (2)	−0.003 (3)	0.012 (3)
C17	0.066 (3)	0.055 (3)	0.061 (3)	−0.018 (2)	−0.004 (2)	−0.006 (2)
C18	0.048 (2)	0.050 (2)	0.045 (2)	−0.0071 (19)	0.0030 (18)	0.0022 (19)
C19	0.043 (2)	0.041 (2)	0.035 (2)	−0.0044 (17)	0.0066 (16)	−0.0081 (16)
C20	0.047 (2)	0.049 (3)	0.068 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C21	0.042 (2)	0.061 (3)	0.084 (3)	0.006 (2)	0.001 (2)	0.003 (3)
C22	0.062 (3)	0.047 (3)	0.063 (3)	0.015 (2)	0.003 (2)	0.005 (2)
C23	0.073 (3)	0.040 (2)	0.053 (3)	0.001 (2)	0.018 (2)	0.0044 (19)
C24	0.045 (2)	0.040 (2)	0.054 (2)	−0.0047 (18)	0.0112 (19)	−0.0038 (18)
N1	0.0405 (18)	0.0381 (18)	0.0483 (19)	−0.0022 (14)	0.0012 (14)	−0.0042 (14)
N2	0.055 (2)	0.046 (2)	0.058 (2)	0.0053 (16)	0.0083 (17)	0.0103 (17)
P1	0.0366 (5)	0.0398 (6)	0.0404 (6)	−0.0027 (4)	0.0058 (4)	0.0008 (4)

C1—C6	1.384 (5)	C12—N2	1.448 (5)
C1—C2	1.402 (5)	C12—H12A	0.96
C1—P1	1.841 (4)	C12—H12B	0.96
C2—C3	1.386 (6)	C12—H12C	0.96
C2—C7	1.504 (6)	C13—C14	1.381 (5)
C3—C4	1.368 (7)	C13—C18	1.386 (5)
C3—H3	0.93	C13—P1	1.829 (4)
C4—C5	1.367 (7)	C14—C15	1.366 (6)
C4—H4	0.93	C14—H14	0.93
C5—C6	1.369 (6)	C15—C16	1.360 (6)
C5—H5	0.93	C15—H15	0.93
C6—H6	0.93	C16—C17	1.361 (6)
C7—N1	1.458 (5)	C16—H16	0.93
C7—H7A	0.97	C17—C18	1.370 (5)
C7—H7B	0.97	C17—H17	0.93
C8—N1	1.452 (5)	C18—H18	0.93
C8—C9	1.510 (5)	C19—C20	1.376 (5)
C8—H8A	0.97	C19—C24	1.391 (5)
C8—H8B	0.97	C19—P1	1.839 (4)
C9—N2	1.450 (5)	C20—C21	1.376 (5)
C9—H9A	0.97	C20—H20	0.93
C9—H9B	0.97	C21—C22	1.359 (6)
C10—N2	1.449 (5)	C21—H21	0.93
C10—C11	1.493 (6)	C22—C23	1.368 (6)
C10—H10A	0.97	C22—H22	0.93
C10—H10B	0.97	C23—C24	1.368 (5)
C11—N1	1.453 (5)	C23—H23	0.93
C11—H11A	0.97	C24—H24	0.93
C11—H11B	0.97	N1—P1	3.051 (3)
C6—C1—C2	118.8 (4)	H12A—C12—H12B	109.5
C6—C1—P1	123.1 (3)	N2—C12—H12C	109.5
C2—C1—P1	118.0 (3)	H12A—C12—H12C	109.5
C3—C2—C1	118.8 (4)	H12B—C12—H12C	109.5
C3—C2—C7	120.6 (4)	C14—C13—C18	117.5 (4)
C1—C2—C7	120.6 (4)	C14—C13—P1	117.3 (3)
C4—C3—C2	121.0 (5)	C18—C13—P1	125.2 (3)
C4—C3—H3	119.5	C15—C14—C13	121.4 (4)
C2—C3—H3	119.5	C15—C14—H14	119.3
C5—C4—C3	120.3 (4)	C13—C14—H14	119.3
C5—C4—H4	119.9	C16—C15—C14	120.3 (4)
C3—C4—H4	119.9	C16—C15—H15	119.8
C4—C5—C6	119.7 (5)	C14—C15—H15	119.8
C4—C5—H5	120.1	C15—C16—C17	119.4 (4)
C6—C5—H5	120.1	C15—C16—H16	120.3
C5—C6—C1	121.4 (4)	C17—C16—H16	120.3
C5—C6—H6	119.3	C16—C17—C18	120.9 (4)
C1—C6—H6	119.3	C16—C17—H17	119.5
N1—C7—C2	111.1 (3)	C18—C17—H17	119.5
N1—C7—H7A	109.4	C17—C18—C13	120.5 (4)
C2—C7—H7A	109.4	C17—C18—H18	119.8
N1—C7—H7B	109.4	C13—C18—H18	119.8
C2—C7—H7B	109.4	C20—C19—C24	117.0 (4)
H7A—C7—H7B	108	C20—C19—P1	124.4 (3)
N1—C8—C9	110.2 (3)	C24—C19—P1	118.2 (3)
N1—C8—H8A	109.6	C19—C20—C21	121.6 (4)
C9—C8—H8A	109.6	C19—C20—H20	119.2
N1—C8—H8B	109.6	C21—C20—H20	119.2
C9—C8—H8B	109.6	C22—C21—C20	120.2 (4)
H8A—C8—H8B	108.1	C22—C21—H21	119.9
N2—C9—C8	111.3 (3)	C20—C21—H21	119.9
N2—C9—H9A	109.4	C21—C22—C23	119.6 (4)
C8—C9—H9A	109.4	C21—C22—H22	120.2
N2—C9—H9B	109.4	C23—C22—H22	120.2
C8—C9—H9B	109.4	C22—C23—C24	120.3 (4)
H9A—C9—H9B	108	C22—C23—H23	119.8
N2—C10—C11	111.5 (4)	C24—C23—H23	119.8
N2—C10—H10A	109.3	C23—C24—C19	121.2 (4)
C11—C10—H10A	109.3	C23—C24—H24	119.4
N2—C10—H10B	109.3	C19—C24—H24	119.4
C11—C10—H10B	109.3	C8—N1—C11	109.7 (3)
H10A—C10—H10B	108	C8—N1—C7	111.9 (3)
N1—C11—C10	110.6 (3)	C11—N1—C7	112.3 (3)
N1—C11—H11A	109.5	C12—N2—C10	111.1 (3)
C10—C11—H11A	109.5	C12—N2—C9	110.5 (3)
N1—C11—H11B	109.5	C10—N2—C9	108.7 (3)
C10—C11—H11B	109.5	C13—P1—C19	101.62 (16)
H11A—C11—H11B	108.1	C13—P1—C1	103.38 (16)
N2—C12—H12A	109.5	C19—P1—C1	100.26 (16)
N2—C12—H12B	109.5
C6—C1—C2—C3	−0.8 (5)	C21—C22—C23—C24	−0.4 (6)
P1—C1—C2—C3	176.2 (3)	C22—C23—C24—C19	−1.2 (6)
C6—C1—C2—C7	177.8 (3)	C20—C19—C24—C23	1.9 (5)
P1—C1—C2—C7	−5.3 (5)	P1—C19—C24—C23	175.7 (3)
C1—C2—C3—C4	0.1 (6)	C9—C8—N1—C11	−57.1 (4)
C7—C2—C3—C4	−178.4 (4)	C9—C8—N1—C7	177.6 (3)
C2—C3—C4—C5	0.8 (7)	C10—C11—N1—C8	57.5 (4)
C3—C4—C5—C6	−1.1 (7)	C10—C11—N1—C7	−177.4 (3)
C4—C5—C6—C1	0.4 (7)	C2—C7—N1—C8	−67.7 (4)
C2—C1—C6—C5	0.5 (6)	C2—C7—N1—C11	168.4 (3)
P1—C1—C6—C5	−176.2 (3)	C11—C10—N2—C12	179.6 (3)
C3—C2—C7—N1	118.9 (4)	C11—C10—N2—C9	57.9 (4)
C1—C2—C7—N1	−59.6 (5)	C8—C9—N2—C12	−179.6 (3)
N1—C8—C9—N2	58.3 (4)	C8—C9—N2—C10	−57.6 (4)
N2—C10—C11—N1	−58.8 (5)	C14—C13—P1—C19	89.3 (3)
C18—C13—C14—C15	0.9 (6)	C18—C13—P1—C19	−93.1 (3)
P1—C13—C14—C15	178.7 (3)	C14—C13—P1—C1	−167.1 (3)
C13—C14—C15—C16	−1.3 (7)	C18—C13—P1—C1	10.5 (4)
C14—C15—C16—C17	1.0 (7)	C20—C19—P1—C13	−21.0 (4)
C15—C16—C17—C18	−0.2 (7)	C24—C19—P1—C13	165.6 (3)
C16—C17—C18—C13	−0.3 (6)	C20—C19—P1—C1	−127.1 (3)
C14—C13—C18—C17	−0.1 (6)	C24—C19—P1—C1	59.5 (3)
P1—C13—C18—C17	−177.7 (3)	C6—C1—P1—C13	−79.7 (3)
C24—C19—C20—C21	−0.9 (6)	C2—C1—P1—C13	103.5 (3)
P1—C19—C20—C21	−174.3 (3)	C6—C1—P1—C19	25.0 (3)
C19—C20—C21—C22	−0.7 (7)	C2—C1—P1—C19	−151.8 (3)
C20—C21—C22—C23	1.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cg3	0.97	2.91	3.835 (4)	160
C14—H14···Cg4i	0.97	2.74	3.651 (5)	166
C23—H23···Cg2ii	0.97	2.98	3.830 (5)	154

C1—P1	1.841 (4)
C13—P1	1.829 (4)
C19—P1	1.839 (4)

C13—P1—C19	101.62 (16)
C13—P1—C1	103.38 (16)
C19—P1—C1	100.26 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cg3	0.97	2.91	3.835 (4)	160
C14—H14⋯Cg4i	0.97	2.74	3.651 (5)	166
C23—H23⋯Cg2ii	0.97	2.98	3.830 (5)	154

Symmetry codes: (i) ; (ii) . Cg2, Cg3, and Cg4 are the centroids of the C1–C6, C13–C18, and C19–C24 benzene rings, respectively.