(2-Chloro­phenyl)­di­phenyl­phosphine

The crystal structure of (2-chloro­phenyl)­di­phenyl­phosphine, C₁₈H₁₄ClP, has been determined at 295 (1) K. The conform­ation of the mol­ecule is similar to that of the analogous 2-bromo and 2-methyl compounds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.115
• Data-to-parameter ratio = 19.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software for Windows; data reduction: TEXSAN (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN; program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN and PLATON (Spek, 2001).

(2-Chlorophenyl)diphenylphosphine

Crystal data

C18H14ClP	Z = 2
Mr = 296.71	F(000) = 308
Triclinic, P1	Dx = 1.293 Mg m^−3
Hall symbol: -P 1	Melting point: 377 - 380 K K
a = 10.646 (8) Å	Mo Kα radiation, λ = 0.71069 Å
b = 10.702 (6) Å	Cell parameters from 25 reflections
c = 8.530 (6) Å	θ = 12.6–16.6°
α = 105.53 (6)°	µ = 0.34 mm^−1
β = 99.88 (6)°	T = 295 K
γ = 119.27 (4)°	Prismatic, colorless
V = 762.1 (11) Å^3	0.30 × 0.30 × 0.30 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.021
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.7°
Graphite monochromator	h = −13→13
ω–2θ scans	k = −13→13
4248 measured reflections	l = −6→11
3483 independent reflections	3 standard reflections every 150 reflections
2452 reflections with I > 2σ(I)	intensity decay: 1.8%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: constr
wR(F^2) = 0.115	H-atom parameters not refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.1312P] where P = (Fo^2 + 2Fc^2)/3
3483 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. The scan width was (1.79 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 5 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.16286 (7)	0.06764 (6)	−0.07477 (8)	0.0644 (2)
P	0.18038 (6)	0.32646 (6)	−0.19819 (7)	0.0468 (2)
C11	0.2241 (2)	0.3628 (2)	0.0340 (2)	0.0467 (6)
C12	0.2166 (2)	0.2465 (2)	0.0838 (3)	0.0508 (6)
C13	0.2477 (3)	0.2626 (3)	0.2551 (3)	0.0658 (8)
C14	0.2906 (3)	0.4007 (3)	0.3822 (3)	0.0743 (9)
C15	0.2993 (3)	0.5193 (3)	0.3397 (3)	0.0763 (9)
C16	0.2663 (3)	0.5006 (3)	0.1667 (3)	0.0619 (7)
C21	−0.0311 (2)	0.2002 (2)	−0.2793 (2)	0.0459 (6)
C22	−0.1076 (3)	0.0858 (3)	−0.4496 (3)	0.0565 (7)
C23	−0.2663 (3)	−0.0190 (3)	−0.5154 (3)	0.0675 (8)
C24	−0.3500 (3)	−0.0104 (3)	−0.4128 (4)	0.0685 (8)
C25	−0.2771 (3)	0.1034 (3)	−0.2456 (4)	0.0661 (9)
C26	−0.1183 (2)	0.2079 (2)	−0.1782 (3)	0.0558 (7)
C31	0.2212 (2)	0.5143 (2)	−0.1954 (2)	0.0477 (6)
C32	0.3758 (2)	0.6357 (3)	−0.1446 (3)	0.0610 (8)
C33	0.4170 (3)	0.7767 (3)	−0.1531 (3)	0.0714 (9)
C34	0.3057 (3)	0.7994 (3)	−0.2154 (3)	0.0692 (9)
C35	0.1523 (3)	0.6810 (3)	−0.2674 (3)	0.0669 (9)
C36	0.1100 (2)	0.5392 (2)	−0.2575 (3)	0.0562 (7)
H13	0.23950	0.17970	0.28390	0.0790*
H14	0.31460	0.41460	0.50070	0.0890*
H15	0.32780	0.61410	0.42850	0.0920*
H16	0.27260	0.58300	0.13860	0.0740*
H22	−0.05000	0.07960	−0.52140	0.0680*
H23	−0.31710	−0.09690	−0.63170	0.0810*
H24	−0.45890	−0.08330	−0.45750	0.0820*
H25	−0.33600	0.11030	−0.17580	0.0790*
H26	−0.06870	0.28540	−0.06180	0.0670*
H32	0.45410	0.62090	−0.10330	0.0730*
H33	0.52290	0.85870	−0.11570	0.0860*
H34	0.33420	0.89620	−0.22260	0.0830*
H35	0.07490	0.69650	−0.31030	0.0800*
H36	0.00380	0.45840	−0.29380	0.0680*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0834 (4)	0.0569 (3)	0.0682 (4)	0.0456 (3)	0.0299 (3)	0.0323 (3)
P	0.0515 (3)	0.0507 (3)	0.0476 (3)	0.0311 (2)	0.0227 (2)	0.0251 (2)
C11	0.0431 (10)	0.0514 (11)	0.0464 (10)	0.0258 (8)	0.0164 (8)	0.0225 (9)
C12	0.0465 (10)	0.0576 (12)	0.0514 (11)	0.0289 (9)	0.0184 (9)	0.0268 (10)
C13	0.0684 (14)	0.0820 (16)	0.0592 (13)	0.0440 (13)	0.0242 (11)	0.0413 (13)
C14	0.0722 (16)	0.0960 (19)	0.0476 (13)	0.0409 (14)	0.0195 (11)	0.0341 (13)
C15	0.0763 (16)	0.0711 (16)	0.0481 (13)	0.0296 (13)	0.0153 (12)	0.0082 (12)
C16	0.0689 (14)	0.0553 (12)	0.0538 (12)	0.0314 (11)	0.0207 (11)	0.0200 (10)
C21	0.0519 (10)	0.0456 (10)	0.0462 (10)	0.0292 (9)	0.0175 (8)	0.0234 (8)
C22	0.0670 (13)	0.0598 (13)	0.0476 (11)	0.0399 (11)	0.0159 (10)	0.0230 (10)
C23	0.0675 (14)	0.0556 (13)	0.0600 (14)	0.0321 (12)	0.0003 (12)	0.0170 (11)
C24	0.0513 (12)	0.0577 (13)	0.0884 (18)	0.0252 (11)	0.0114 (12)	0.0388 (13)
C25	0.0566 (13)	0.0655 (14)	0.0867 (17)	0.0329 (12)	0.0339 (12)	0.0431 (13)
C26	0.0549 (12)	0.0535 (12)	0.0582 (12)	0.0284 (10)	0.0243 (10)	0.0235 (10)
C31	0.0525 (11)	0.0517 (11)	0.0456 (10)	0.0292 (9)	0.0231 (9)	0.0256 (9)
C32	0.0519 (12)	0.0622 (13)	0.0749 (14)	0.0300 (10)	0.0263 (11)	0.0382 (12)
C33	0.0668 (15)	0.0589 (14)	0.0794 (17)	0.0242 (12)	0.0293 (13)	0.0369 (13)
C34	0.0876 (17)	0.0527 (13)	0.0715 (15)	0.0364 (13)	0.0316 (13)	0.0355 (12)
C35	0.0790 (16)	0.0647 (14)	0.0705 (15)	0.0466 (13)	0.0247 (13)	0.0349 (12)
C36	0.0571 (12)	0.0558 (12)	0.0603 (13)	0.0324 (10)	0.0212 (10)	0.0286 (10)

Geometric parameters (Å, º)

Cl—C12	1.760 (3)	C32—C33	1.377 (4)
P—C11	1.840 (2)	C33—C34	1.371 (5)
P—C21	1.834 (3)	C34—C35	1.377 (5)
P—C31	1.830 (3)	C35—C36	1.388 (4)
C11—C12	1.391 (3)	C13—H13	0.9505
C11—C16	1.393 (3)	C14—H14	0.9502
C12—C13	1.385 (3)	C15—H15	0.9506
C13—C14	1.371 (4)	C16—H16	0.9489
C14—C15	1.376 (4)	C22—H22	0.9500
C15—C16	1.392 (4)	C23—H23	0.9507
C21—C22	1.392 (3)	C24—H24	0.9501
C21—C26	1.387 (3)	C25—H25	0.9503
C22—C23	1.383 (5)	C26—H26	0.9505
C23—C24	1.369 (5)	C32—H32	0.9499
C24—C25	1.373 (4)	C33—H33	0.9498
C25—C26	1.383 (4)	C34—H34	0.9498
C31—C32	1.396 (4)	C35—H35	0.9503
C31—C36	1.386 (3)	C36—H36	0.9499
Cl···P	3.153 (3)	C31···H14^vii	3.0476
Cl···C21	3.503 (3)	C32···H16	2.8974
Cl···Cl^i	3.653 (3)	C32···H14^vii	3.0266
Cl···H22^ii	3.1007	C35···H26^viii	3.0719
Cl···H33^iii	3.0533	H13···C23^i	3.0073
P···Cl	3.153 (3)	H13···C24^i	2.9296
C16···C32	3.460 (5)	H14···C31^ix	3.0476
C21···Cl	3.503 (3)	H14···C32^ix	3.0265
C24···C24^iv	3.421 (6)	H16···C31	2.6281
C26···C36	3.515 (4)	H16···C32	2.8974
C32···C16	3.460 (5)	H22···Cl^ii	3.1007
C36···C26	3.515 (4)	H22···C22^ii	2.9701
C11···H26	2.7035	H22···H22^ii	2.4785
C12···H32^iii	3.0233	H24···C24^iv	2.8610
C16···H26	3.0002	H24···H24^iv	2.5437
C21···H36	2.6427	H26···C11	2.7035
C22···H22^ii	2.9701	H26···C16	3.0002
C23···H34^v	3.0318	H26···C35^viii	3.0719
C23···H13^i	3.0073	H32···C12^iii	3.0233
C24···H24^iv	2.8610	H33···C25^x	3.0871
C24···H13^i	2.9296	H33···Cl^iii	3.0533
C25···H33^vi	3.0871	H34···C23^v	3.0318
C26···H36	2.8804	H36···C21	2.6427
C31···H16	2.6281	H36···C26	2.8804
C11—P—C21	100.23 (11)	C12—C13—H13	120.69
C11—P—C31	102.47 (10)	C14—C13—H13	120.74
C21—P—C31	103.26 (12)	C13—C14—H14	119.66
P—C11—C12	118.67 (16)	C15—C14—H14	119.73
P—C11—C16	124.73 (18)	C14—C15—H15	120.04
C12—C11—C16	116.59 (19)	C16—C15—H15	119.91
Cl—C12—C11	119.92 (17)	C11—C16—H16	119.45
Cl—C12—C13	117.0 (2)	C15—C16—H16	119.48
C11—C12—C13	123.1 (2)	C21—C22—H22	119.57
C12—C13—C14	118.6 (3)	C23—C22—H22	119.60
C13—C14—C15	120.6 (2)	C22—C23—H23	120.01
C14—C15—C16	120.1 (3)	C24—C23—H23	120.10
C11—C16—C15	121.1 (3)	C23—C24—H24	119.88
P—C21—C22	118.0 (2)	C25—C24—H24	119.91
P—C21—C26	123.65 (15)	C24—C25—H25	119.86
C22—C21—C26	118.3 (2)	C26—C25—H25	119.84
C21—C22—C23	120.8 (3)	C21—C26—H26	119.85
C22—C23—C24	119.9 (3)	C25—C26—H26	119.72
C23—C24—C25	120.2 (3)	C31—C32—H32	119.42
C24—C25—C26	120.3 (3)	C33—C32—H32	119.36
C21—C26—C25	120.4 (2)	C32—C33—H33	119.98
P—C31—C32	117.1 (2)	C34—C33—H33	119.74
P—C31—C36	124.68 (17)	C33—C34—H34	120.22
C32—C31—C36	117.8 (2)	C35—C34—H34	120.19
C31—C32—C33	121.2 (3)	C34—C35—H35	119.78
C32—C33—C34	120.3 (3)	C36—C35—H35	119.79
C33—C34—C35	119.6 (3)	C31—C36—H36	119.71
C34—C35—C36	120.4 (3)	C35—C36—H36	119.65
C31—C36—C35	120.6 (2)
C21—P—C11—C12	78.5 (2)	C12—C13—C14—C15	1.4 (5)
C21—P—C11—C16	−102.2 (3)	C13—C14—C15—C16	−0.8 (5)
C31—P—C11—C12	−175.3 (2)	C14—C15—C16—C11	0.0 (5)
C31—P—C11—C16	4.0 (3)	P—C21—C22—C23	176.3 (2)
C11—P—C21—C22	−148.2 (2)	C26—C21—C22—C23	−1.0 (4)
C11—P—C21—C26	28.9 (2)	P—C21—C26—C25	−176.6 (2)
C31—P—C21—C22	106.3 (2)	C22—C21—C26—C25	0.4 (4)
C31—P—C21—C26	−76.6 (2)	C21—C22—C23—C24	0.3 (5)
C11—P—C31—C32	78.48 (18)	C22—C23—C24—C25	0.9 (5)
C11—P—C31—C36	−108.81 (19)	C23—C24—C25—C26	−1.5 (5)
C21—P—C31—C32	−177.69 (16)	C24—C25—C26—C21	0.8 (4)
C21—P—C31—C36	−5.0 (2)	P—C31—C32—C33	174.24 (19)
P—C11—C12—Cl	−1.1 (3)	C36—C31—C32—C33	1.0 (3)
P—C11—C12—C13	179.9 (2)	P—C31—C36—C35	−173.01 (19)
C16—C11—C12—Cl	179.5 (2)	C32—C31—C36—C35	−0.3 (3)
C16—C11—C12—C13	0.4 (4)	C31—C32—C33—C34	−1.3 (4)
P—C11—C16—C15	−179.2 (3)	C32—C33—C34—C35	0.8 (4)
C12—C11—C16—C15	0.2 (4)	C33—C34—C35—C36	−0.2 (4)
Cl—C12—C13—C14	179.7 (3)	C34—C35—C36—C31	−0.1 (4)
C11—C12—C13—C14	−1.2 (5)

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y, −z−1; (iii) −x+1, −y+1, −z; (iv) −x−1, −y, −z−1; (v) −x, −y+1, −z−1; (vi) x−1, y−1, z; (vii) x, y, z−1; (viii) −x, −y+1, −z; (ix) x, y, z+1; (x) x+1, y+1, z.