8-(Diphenyl-phosphan-yl)quinoline.

The title compound, C(21)H(16)NP, is a known P-N chelator and various crystal structures of its metal complexes have been reported. However, no crystallographic evidence of the free ligand has been given to date. The phenyl rings are almost orthogonal to one another [dihedral angle = 88.9 (1)°], and they are twisted from the mean plane of the quinoline by 80.5 (1) and 76.3 (1)°.

Related literature

Synthetic details regarding this compound were reported by Issleib & Haftendorn (1970 ▶); Feltham & Metzger (1971 ▶); Lai et al. (2001 ▶); Lord et al. (2009 ▶). For the crystal structures of some of its metal complexes, see: Hudali et al. (1979 ▶); Sun et al. (2002 ▶); Suzuki (2004 ▶); Suzuki et al. (2009 ▶); Canovese et al. (2008 ▶); Qin et al. (2009 ▶); Tsukuda et al. (2009 ▶). The propeller-type conformation of the title compound is characteristic for tris-(ar­yl)-substituted phosphines, see: Beck et al. (2008 ▶). For C—P—C angles in related structures, see: Van Allen & Venkataraman (2003 ▶); Chuit et al. (1993 ▶). For hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C21H16NP

M = 313.32

Monoclinic,

a = 10.7804 (2) Å

b = 16.6905 (3) Å

c = 9.7753 (2) Å

β = 112.651 (1)°

V = 1623.21 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.47 mm−1

T = 150 K

0.20 × 0.18 × 0.12 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.658, T max = 0.839

20905 measured reflections

3170 independent reflections

3067 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.07

3170 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: UdMX (Maris, 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040237/nk2063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040237/nk2063Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H16NP	F(000) = 656
Mr = 313.32	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9934 reflections
a = 10.7804 (2) Å	θ = 4.4–72.3°
b = 16.6905 (3) Å	µ = 1.47 mm−1
c = 9.7753 (2) Å	T = 150 K
β = 112.651 (1)°	Block, colourless
V = 1623.21 (5) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Bruker APEXII diffractometer	3170 independent reflections
Radiation source: Rotating Anode	3067 reflections with I > 2σ(I)
Helios optics	Rint = 0.028
Detector resolution: 5.5 pixels mm-1	θmax = 72.4°, θmin = 4.4°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
Tmin = 0.658, Tmax = 0.839	l = −12→12
20905 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.4334P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3170 reflections	Δρmax = 0.28 e Å−3
209 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0148 (8)

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4 K Charged-Coupled Device (CCD) Area Detector using the program APEX2 and a Nonius FR591 rotating anode equiped with a Montel 200 optics The crystal-to-detector distance was 5.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over four different parts of the reciprocal space (132 frames total). One complete sphere of data was collected, to better than 0.80Å resolution.

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
P1	0.85952 (3)	1.005358 (18)	0.64679 (3)	0.02256 (14)
N1	0.93166 (11)	0.84034 (6)	0.73402 (12)	0.0271 (3)
C1	0.97809 (14)	0.76959 (8)	0.79118 (16)	0.0314 (3)
H1	1.0426	0.7678	0.8901	0.038*
C2	0.93792 (15)	0.69649 (8)	0.71462 (17)	0.0352 (3)
H2	0.9740	0.6472	0.7619	0.042*
C3	0.84690 (14)	0.69733 (8)	0.57230 (17)	0.0337 (3)
H3	0.8207	0.6488	0.5181	0.040*
C4	0.79150 (13)	0.77131 (7)	0.50553 (15)	0.0270 (3)
C5	0.69380 (14)	0.77770 (8)	0.35912 (16)	0.0319 (3)
H5	0.6625	0.7309	0.3007	0.038*
C6	0.64444 (14)	0.85111 (8)	0.30167 (15)	0.0320 (3)
H6	0.5788	0.8549	0.2035	0.038*
C7	0.69018 (13)	0.92151 (8)	0.38711 (14)	0.0276 (3)
H7	0.6544	0.9720	0.3455	0.033*
C8	0.78570 (12)	0.91807 (7)	0.52963 (13)	0.0229 (3)
C9	0.83787 (12)	0.84184 (7)	0.59135 (14)	0.0238 (3)
C10	0.76718 (12)	1.08881 (7)	0.52806 (13)	0.0236 (3)
C11	0.66326 (13)	1.13098 (8)	0.54748 (14)	0.0282 (3)
H11	0.6300	1.1134	0.6193	0.034*
C12	0.60791 (15)	1.19864 (8)	0.46244 (16)	0.0337 (3)
H12	0.5381	1.2273	0.4775	0.040*
C13	0.65439 (15)	1.22434 (9)	0.35592 (16)	0.0343 (3)
H13	0.6172	1.2708	0.2988	0.041*
C14	0.75532 (14)	1.18199 (9)	0.33304 (16)	0.0345 (3)
H14	0.7853	1.1985	0.2580	0.041*
C15	0.81267 (13)	1.11546 (8)	0.41960 (15)	0.0298 (3)
H15	0.8836	1.0877	0.4051	0.036*
C16	0.77946 (14)	1.00053 (7)	0.78177 (15)	0.0243 (3)
C17	0.66076 (13)	0.95868 (7)	0.75734 (15)	0.0275 (3)
H17	0.6172	0.9308	0.6666	0.033*
C18	0.60580 (14)	0.95742 (8)	0.86437 (16)	0.0326 (3)
H18	0.5249	0.9288	0.8467	0.039*
C19	0.66880 (17)	0.99806 (8)	0.99754 (17)	0.0361 (4)
H19	0.6311	0.9971	1.0708	0.043*
C20	0.78696 (15)	1.04008 (9)	1.02311 (15)	0.0367 (3)
H20	0.8300	1.0680	1.1138	0.044*
C21	0.84206 (14)	1.04117 (8)	0.91598 (15)	0.0308 (3)
H21	0.9230	1.0698	0.9341	0.037*

	U11	U22	U33	U12	U13	U23
P1	0.0238 (2)	0.0191 (2)	0.0238 (2)	−0.00020 (10)	0.00809 (15)	−0.00011 (10)
N1	0.0270 (5)	0.0253 (5)	0.0283 (6)	0.0019 (4)	0.0100 (4)	0.0023 (4)
C1	0.0292 (7)	0.0299 (7)	0.0345 (7)	0.0042 (5)	0.0115 (6)	0.0063 (5)
C2	0.0342 (7)	0.0243 (6)	0.0477 (8)	0.0069 (5)	0.0166 (6)	0.0085 (6)
C3	0.0358 (7)	0.0210 (6)	0.0470 (8)	−0.0002 (5)	0.0190 (6)	−0.0024 (6)
C4	0.0284 (6)	0.0223 (6)	0.0335 (7)	−0.0013 (5)	0.0155 (5)	−0.0014 (5)
C5	0.0360 (7)	0.0257 (6)	0.0338 (7)	−0.0057 (5)	0.0131 (6)	−0.0084 (5)
C6	0.0338 (7)	0.0320 (7)	0.0254 (6)	−0.0043 (5)	0.0062 (5)	−0.0024 (5)
C7	0.0300 (6)	0.0237 (6)	0.0271 (6)	−0.0001 (5)	0.0089 (5)	0.0016 (5)
C8	0.0248 (6)	0.0206 (6)	0.0246 (6)	−0.0006 (4)	0.0109 (5)	−0.0008 (4)
C9	0.0241 (6)	0.0227 (6)	0.0270 (6)	−0.0006 (4)	0.0124 (5)	−0.0003 (5)
C10	0.0256 (6)	0.0189 (6)	0.0244 (6)	−0.0023 (4)	0.0075 (5)	−0.0023 (4)
C11	0.0333 (7)	0.0252 (6)	0.0281 (6)	0.0022 (5)	0.0140 (5)	0.0010 (5)
C12	0.0372 (7)	0.0302 (7)	0.0343 (7)	0.0101 (6)	0.0145 (6)	0.0033 (6)
C13	0.0385 (8)	0.0273 (7)	0.0346 (7)	0.0051 (5)	0.0112 (6)	0.0090 (5)
C14	0.0365 (7)	0.0352 (7)	0.0340 (7)	0.0004 (6)	0.0161 (6)	0.0089 (6)
C15	0.0293 (6)	0.0296 (7)	0.0328 (7)	0.0019 (5)	0.0144 (5)	0.0026 (5)
C16	0.0282 (7)	0.0208 (6)	0.0227 (6)	0.0037 (4)	0.0084 (5)	0.0027 (4)
C17	0.0289 (6)	0.0245 (6)	0.0278 (6)	0.0005 (5)	0.0096 (5)	0.0006 (5)
C18	0.0316 (7)	0.0311 (7)	0.0380 (7)	0.0044 (5)	0.0165 (6)	0.0056 (6)
C19	0.0431 (9)	0.0401 (8)	0.0306 (8)	0.0128 (6)	0.0203 (7)	0.0070 (5)
C20	0.0435 (8)	0.0387 (8)	0.0256 (7)	0.0072 (6)	0.0106 (6)	−0.0044 (6)
C21	0.0319 (7)	0.0287 (7)	0.0285 (7)	0.0004 (5)	0.0079 (5)	−0.0030 (5)

P1—C8	1.8345 (12)	C10—C15	1.4010 (18)
P1—C16	1.8357 (14)	C11—C12	1.3930 (18)
P1—C10	1.8408 (12)	C11—H11	0.9500
N1—C1	1.3196 (17)	C12—C13	1.386 (2)
N1—C9	1.3718 (16)	C12—H12	0.9500
C1—C2	1.410 (2)	C13—C14	1.386 (2)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.359 (2)	C14—C15	1.3887 (19)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.4167 (19)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.3953 (18)
C4—C5	1.417 (2)	C16—C21	1.3982 (18)
C4—C9	1.4200 (17)	C17—C18	1.3869 (19)
C5—C6	1.367 (2)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.391 (2)
C6—C7	1.4158 (18)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.390 (2)
C7—C8	1.3783 (18)	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.389 (2)
C8—C9	1.4275 (16)	C20—H20	0.9500
C10—C11	1.3964 (18)	C21—H21	0.9500
C8—P1—C16	101.70 (6)	C12—C11—C10	120.61 (12)
C8—P1—C10	102.01 (6)	C12—C11—H11	119.7
C16—P1—C10	101.34 (6)	C10—C11—H11	119.7
C1—N1—C9	117.24 (11)	C13—C12—C11	120.23 (13)
N1—C1—C2	124.12 (13)	C13—C12—H12	119.9
N1—C1—H1	117.9	C11—C12—H12	119.9
C2—C1—H1	117.9	C14—C13—C12	119.79 (13)
C3—C2—C1	119.18 (12)	C14—C13—H13	120.1
C3—C2—H2	120.4	C12—C13—H13	120.1
C1—C2—H2	120.4	C13—C14—C15	120.16 (13)
C2—C3—C4	119.39 (13)	C13—C14—H14	119.9
C2—C3—H3	120.3	C15—C14—H14	119.9
C4—C3—H3	120.3	C14—C15—C10	120.76 (12)
C3—C4—C5	123.26 (12)	C14—C15—H15	119.6
C3—C4—C9	117.40 (12)	C10—C15—H15	119.6
C5—C4—C9	119.33 (12)	C17—C16—C21	118.87 (12)
C6—C5—C4	120.18 (12)	C17—C16—P1	123.58 (10)
C6—C5—H5	119.9	C21—C16—P1	117.55 (10)
C4—C5—H5	119.9	C18—C17—C16	120.56 (13)
C5—C6—C7	120.63 (12)	C18—C17—H17	119.7
C5—C6—H6	119.7	C16—C17—H17	119.7
C7—C6—H6	119.7	C17—C18—C19	120.14 (14)
C8—C7—C6	121.10 (12)	C17—C18—H18	119.9
C8—C7—H7	119.4	C19—C18—H18	119.9
C6—C7—H7	119.4	C20—C19—C18	119.85 (13)
C7—C8—C9	118.93 (11)	C20—C19—H19	120.1
C7—C8—P1	124.99 (9)	C18—C19—H19	120.1
C9—C8—P1	116.00 (9)	C21—C20—C19	119.97 (13)
N1—C9—C4	122.64 (11)	C21—C20—H20	120.0
N1—C9—C8	117.52 (11)	C19—C20—H20	120.0
C4—C9—C8	119.83 (11)	C20—C21—C16	120.61 (13)
C11—C10—C15	118.41 (12)	C20—C21—H21	119.7
C11—C10—P1	124.26 (10)	C16—C21—H21	119.7
C15—C10—P1	117.09 (10)
C9—N1—C1—C2	0.41 (19)	C8—P1—C10—C11	103.60 (11)
N1—C1—C2—C3	0.8 (2)	C16—P1—C10—C11	−1.13 (12)
C1—C2—C3—C4	−1.8 (2)	C8—P1—C10—C15	−82.02 (11)
C2—C3—C4—C5	−178.48 (13)	C16—P1—C10—C15	173.26 (10)
C2—C3—C4—C9	1.73 (19)	C15—C10—C11—C12	−1.01 (19)
C3—C4—C5—C6	179.91 (13)	P1—C10—C11—C12	173.30 (10)
C9—C4—C5—C6	−0.3 (2)	C10—C11—C12—C13	0.8 (2)
C4—C5—C6—C7	0.1 (2)	C11—C12—C13—C14	0.7 (2)
C5—C6—C7—C8	0.3 (2)	C12—C13—C14—C15	−2.0 (2)
C6—C7—C8—C9	−0.50 (19)	C13—C14—C15—C10	1.8 (2)
C6—C7—C8—P1	176.31 (10)	C11—C10—C15—C14	−0.30 (19)
C16—P1—C8—C7	107.19 (11)	P1—C10—C15—C14	−175.03 (11)
C10—P1—C8—C7	2.74 (13)	C8—P1—C16—C17	−20.27 (12)
C16—P1—C8—C9	−75.92 (10)	C10—P1—C16—C17	84.70 (11)
C10—P1—C8—C9	179.64 (9)	C8—P1—C16—C21	159.62 (10)
C1—N1—C9—C4	−0.49 (18)	C10—P1—C16—C21	−95.41 (11)
C1—N1—C9—C8	179.06 (11)	C21—C16—C17—C18	0.00 (19)
C3—C4—C9—N1	−0.56 (18)	P1—C16—C17—C18	179.90 (10)
C5—C4—C9—N1	179.64 (11)	C16—C17—C18—C19	0.0 (2)
C3—C4—C9—C8	179.90 (11)	C17—C18—C19—C20	0.1 (2)
C5—C4—C9—C8	0.09 (18)	C18—C19—C20—C21	−0.2 (2)
C7—C8—C9—N1	−179.27 (11)	C19—C20—C21—C16	0.2 (2)
P1—C8—C9—N1	3.64 (15)	C17—C16—C21—C20	−0.13 (19)
C7—C8—C9—C4	0.30 (18)	P1—C16—C21—C20	179.97 (10)
P1—C8—C9—C4	−176.79 (9)