Literature DB >> 23476292

Tris(naphthalen-1-yl)phosphane chloro-form hemisolvate.

Abstract

The title compound, P(C10H7)3·0.5CHCl3, was isolated after the unsuccessful reaction of KSeCN and tris-(naphthalen-1-yl)phosphane. The solvent mol-ecule is disordered about an inversion center. The effective cone angle of the phosphine is 203°. In the crystal, weak C-H⋯Cl and C-H⋯π inter-actions are observed.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 23476292 PMCID： PMC3589056 DOI： 10.1107/S1600536812048234

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to the investigation of the steric and electronic properties of phosphorus-containing ligands, see: Otto & Roodt (2004 ▶); Cowley & Damasco (1971 ▶); Allen & Taylor (1982 ▶); Allen et al. (1985 ▶); Muller et al. (2008 ▶). For background to cone angles, see: Tolman (1977 ▶); Otto (2001 ▶).

Experimental

Crystal data

C30H21P·0.5CHCl3 M = 472.12 Monoclinic, a = 9.197 (3) Å b = 14.564 (5) Å c = 18.675 (5) Å β = 107.061 (14)° V = 2391.3 (13) Å3 Z = 4 Mo Kα radiation μ = 0.3 mm−1 T = 100 K 0.3 × 0.07 × 0.07 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.916, T max = 0.979 23695 measured reflections 5950 independent reflections 3713 reflections with I > 2σ(I) R int = 0.107

Refinement

R[F 2 > 2σ(F 2)] = 0.066 wR(F 2) = 0.194 S = 1.02 5950 reflections 316 parameters H-atom parameters constrained Δρmax = 0.87 e Å−3 Δρmin = −0.57 e Å−3 Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 2012 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048234/lh5561sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048234/lh5561Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812048234/lh5561Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₃₀H₂₁P·0.5CHCl₃	F(000) = 980
M_r = 472.12	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2813 reflections
a = 9.197 (3) Å	θ = 2.3–24.3°
b = 14.564 (5) Å	µ = 0.3 mm⁻¹
c = 18.675 (5) Å	T = 100 K
β = 107.061 (14)°	Needle, colourless
V = 2391.3 (13) Å³	0.3 × 0.07 × 0.07 mm
Z = 4

Bruker APEX DUO 4K-CCD diffractometer	5950 independent reflections
Radiation source: sealed tube	3713 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.107
Detector resolution: 8.4 pixels mm^-1	θ_max = 28.4°, θ_min = 1.8°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −18→19
T_min = 0.916, T_max = 0.979	l = −24→24
23695 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1042P)² + 0.0263P] where P = (F_o² + 2F_c²)/3
5950 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 120 s/frame. A total of 1041 frames were collected with a frame width of 0.5° covering up to θ = 28.38° with 99.2% completeness accomplished.

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	U_iso*/U_eq	Occ. (<1)
P1	0.73007 (7)	0.85270 (5)	0.62816 (4)	0.02204 (18)
C1	0.6589 (3)	0.80104 (19)	0.53493 (14)	0.0251 (5)
C2	0.7611 (3)	0.74531 (18)	0.50785 (15)	0.0269 (6)
C3	0.9148 (3)	0.72986 (19)	0.54983 (15)	0.0277 (6)
H3	0.9534	0.7578	0.5963	0.033*
C4	1.0071 (4)	0.6744 (2)	0.52300 (17)	0.0373 (7)
H4	1.1069	0.664	0.5518	0.045*
C5	0.9517 (5)	0.6332 (2)	0.4522 (2)	0.0502 (9)
H5	1.0149	0.5956	0.4343	0.06*
C6	0.8055 (4)	0.6484 (2)	0.40970 (18)	0.0474 (9)
H6	0.7708	0.6216	0.3625	0.057*
C7	0.7056 (4)	0.7039 (2)	0.43570 (16)	0.0353 (7)
C8	0.5525 (4)	0.7185 (2)	0.39308 (17)	0.0439 (8)
H8	0.5166	0.6925	0.3457	0.053*
C9	0.4568 (4)	0.7699 (2)	0.42033 (18)	0.0427 (8)
H9	0.3559	0.7775	0.3921	0.051*
C10	0.5105 (3)	0.8114 (2)	0.49096 (17)	0.0354 (7)
H10	0.4443	0.8469	0.5086	0.042*
C11	0.8153 (3)	0.95984 (18)	0.60744 (15)	0.0243 (5)
C12	0.9083 (3)	1.01264 (17)	0.66864 (15)	0.0237 (5)
C13	0.9367 (3)	0.98622 (19)	0.74493 (15)	0.0265 (6)
H13	0.8914	0.9334	0.7565	0.032*
C14	1.0293 (3)	1.0370 (2)	0.80119 (16)	0.0312 (6)
H14	1.0476	1.0181	0.8506	0.037*
C15	1.0980 (3)	1.1185 (2)	0.78521 (17)	0.0325 (6)
H15	1.1608	1.1529	0.824	0.039*
C16	1.0719 (3)	1.14612 (19)	0.71339 (16)	0.0302 (6)
H16	1.1168	1.2	0.7035	0.036*
C17	0.9776 (3)	1.09469 (18)	0.65280 (16)	0.0262 (6)
C18	0.9538 (3)	1.12187 (19)	0.57754 (17)	0.0316 (6)
H18	0.999	1.1754	0.5672	0.038*
C19	0.8659 (3)	1.0710 (2)	0.52010 (16)	0.0307 (6)
H19	0.8516	1.0895	0.4709	0.037*
C20	0.7961 (3)	0.98966 (19)	0.53533 (16)	0.0281 (6)
H20	0.7357	0.9555	0.4956	0.034*
C21	0.5560 (3)	0.89395 (18)	0.64718 (14)	0.0238 (5)
C22	0.5185 (3)	0.98566 (19)	0.64516 (15)	0.0270 (6)
H22	0.5778	1.028	0.6289	0.032*
C23	0.3931 (3)	1.01723 (19)	0.66694 (15)	0.0293 (6)
H23	0.3705	1.0796	0.6647	0.035*
C24	0.3042 (3)	0.9567 (2)	0.69129 (15)	0.0269 (6)
H24	0.2224	0.9783	0.7061	0.032*
C25	0.3358 (3)	0.86131 (19)	0.69407 (14)	0.0248 (5)
C26	0.2434 (3)	0.7973 (2)	0.71761 (15)	0.0302 (6)
H26	0.1604	0.8183	0.7318	0.036*
C27	0.2735 (3)	0.7053 (2)	0.71984 (16)	0.0344 (7)
H27	0.212	0.6642	0.7357	0.041*
C28	0.3985 (3)	0.6730 (2)	0.69789 (17)	0.0345 (7)
H28	0.4186	0.6103	0.699	0.041*
C29	0.4911 (3)	0.73308 (19)	0.67483 (16)	0.0297 (6)
H29	0.5735	0.7105	0.661	0.036*
C30	0.4632 (3)	0.82826 (18)	0.67181 (15)	0.0248 (6)
Cl1	0.68271 (18)	0.46375 (16)	0.50033 (11)	0.0583 (5)	0.5
Cl2	0.3885 (2)	0.49626 (13)	0.39948 (12)	0.0646 (6)	0.5
Cl3	0.4575 (3)	0.55581 (16)	0.55292 (13)	0.0727 (6)	0.5
C31	0.4885 (7)	0.4716 (4)	0.4923 (4)	0.0397 (14)	0.5
H31	0.4538	0.4123	0.5059	0.048*	0.5

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0227 (3)	0.0153 (3)	0.0283 (4)	0.0009 (2)	0.0078 (3)	0.0026 (3)
C1	0.0304 (13)	0.0181 (13)	0.0257 (13)	−0.0033 (10)	0.0064 (11)	0.0056 (11)
C2	0.0379 (14)	0.0167 (13)	0.0263 (14)	−0.0059 (11)	0.0100 (12)	0.0026 (11)
C3	0.0392 (14)	0.0205 (14)	0.0267 (14)	−0.0006 (11)	0.0149 (12)	0.0035 (11)
C4	0.0479 (17)	0.0290 (16)	0.0412 (17)	0.0038 (13)	0.0229 (14)	0.0015 (14)
C5	0.080 (3)	0.0308 (19)	0.055 (2)	−0.0040 (16)	0.042 (2)	−0.0103 (16)
C6	0.078 (2)	0.0366 (19)	0.0331 (17)	−0.0182 (17)	0.0254 (17)	−0.0112 (15)
C7	0.0557 (18)	0.0221 (15)	0.0292 (15)	−0.0128 (13)	0.0143 (14)	0.0002 (12)
C8	0.061 (2)	0.0358 (19)	0.0274 (16)	−0.0208 (15)	0.0018 (15)	0.0008 (14)
C9	0.0409 (16)	0.041 (2)	0.0363 (17)	−0.0134 (14)	−0.0040 (14)	0.0095 (15)
C10	0.0340 (14)	0.0288 (17)	0.0368 (16)	−0.0055 (12)	0.0002 (13)	0.0099 (13)
C11	0.0214 (11)	0.0177 (13)	0.0351 (15)	0.0024 (9)	0.0102 (11)	0.0032 (11)
C12	0.0231 (11)	0.0154 (12)	0.0354 (15)	0.0014 (9)	0.0129 (11)	0.0014 (11)
C13	0.0302 (13)	0.0179 (13)	0.0351 (15)	−0.0013 (10)	0.0153 (12)	−0.0001 (11)
C14	0.0419 (15)	0.0260 (15)	0.0305 (15)	−0.0044 (12)	0.0180 (13)	−0.0054 (12)
C15	0.0361 (14)	0.0226 (15)	0.0427 (17)	−0.0059 (11)	0.0178 (13)	−0.0103 (13)
C16	0.0338 (13)	0.0159 (13)	0.0458 (17)	−0.0035 (10)	0.0196 (13)	−0.0045 (12)
C17	0.0265 (12)	0.0151 (13)	0.0402 (16)	0.0015 (10)	0.0149 (11)	0.0007 (11)
C18	0.0345 (14)	0.0175 (14)	0.0468 (17)	−0.0016 (10)	0.0181 (13)	0.0070 (12)
C19	0.0337 (14)	0.0243 (15)	0.0349 (16)	0.0014 (11)	0.0115 (12)	0.0108 (12)
C20	0.0278 (13)	0.0205 (14)	0.0356 (15)	0.0008 (10)	0.0088 (12)	0.0027 (12)
C21	0.0217 (11)	0.0187 (13)	0.0306 (14)	0.0016 (9)	0.0071 (11)	0.0045 (11)
C22	0.0256 (12)	0.0181 (13)	0.0375 (16)	0.0014 (10)	0.0098 (12)	0.0068 (11)
C23	0.0306 (14)	0.0201 (14)	0.0362 (16)	0.0056 (11)	0.0081 (12)	0.0019 (12)
C24	0.0222 (12)	0.0290 (15)	0.0291 (14)	0.0048 (10)	0.0068 (11)	0.0019 (12)
C25	0.0204 (11)	0.0268 (14)	0.0252 (13)	0.0000 (10)	0.0036 (10)	0.0039 (11)
C26	0.0220 (12)	0.0346 (16)	0.0323 (15)	−0.0031 (11)	0.0053 (11)	0.0049 (13)
C27	0.0294 (13)	0.0329 (16)	0.0393 (17)	−0.0092 (12)	0.0075 (12)	0.0091 (13)
C28	0.0334 (14)	0.0202 (14)	0.0476 (18)	−0.0021 (11)	0.0081 (13)	0.0086 (13)
C29	0.0275 (13)	0.0212 (14)	0.0410 (17)	0.0033 (10)	0.0110 (12)	0.0095 (12)
C30	0.0246 (12)	0.0206 (14)	0.0286 (14)	−0.0009 (10)	0.0069 (11)	0.0038 (11)
Cl1	0.0349 (8)	0.0726 (14)	0.0590 (12)	0.0079 (8)	0.0009 (8)	−0.0100 (10)
Cl2	0.0631 (11)	0.0349 (10)	0.0680 (13)	0.0079 (8)	−0.0239 (10)	−0.0142 (9)
Cl3	0.0889 (15)	0.0602 (14)	0.0794 (15)	0.0005 (11)	0.0409 (13)	−0.0266 (12)
C31	0.046 (3)	0.026 (3)	0.051 (4)	−0.009 (3)	0.020 (3)	−0.008 (3)

P1—C1	1.832 (3)	C16—C17	1.420 (4)
P1—C11	1.838 (3)	C16—H16	0.93
P1—C21	1.840 (2)	C17—C18	1.414 (4)
C1—C10	1.379 (4)	C18—C19	1.358 (4)
C1—C2	1.441 (4)	C18—H18	0.93
C2—C3	1.419 (4)	C19—C20	1.415 (4)
C2—C7	1.427 (4)	C19—H19	0.93
C3—C4	1.369 (4)	C20—H20	0.93
C3—H3	0.93	C21—C22	1.377 (4)
C4—C5	1.404 (5)	C21—C30	1.444 (3)
C4—H4	0.93	C22—C23	1.408 (3)
C5—C6	1.364 (5)	C22—H22	0.93
C5—H5	0.93	C23—C24	1.368 (4)
C6—C7	1.413 (5)	C23—H23	0.93
C6—H6	0.93	C24—C25	1.417 (4)
C7—C8	1.415 (5)	C24—H24	0.93
C8—C9	1.363 (5)	C25—C26	1.416 (4)
C8—H8	0.93	C25—C30	1.436 (3)
C9—C10	1.403 (4)	C26—C27	1.367 (4)
C9—H9	0.93	C26—H26	0.93
C10—H10	0.93	C27—C28	1.410 (4)
C11—C20	1.376 (4)	C27—H27	0.93
C11—C12	1.434 (4)	C28—C29	1.375 (4)
C12—C13	1.424 (4)	C28—H28	0.93
C12—C17	1.426 (4)	C29—C30	1.408 (4)
C13—C14	1.360 (4)	C29—H29	0.93
C13—H13	0.93	Cl1—C31	1.752 (7)
C14—C15	1.416 (4)	Cl2—C31	1.745 (8)
C14—H14	0.93	Cl3—C31	1.748 (7)
C15—C16	1.353 (4)	C31—H31	0.98
C15—H15	0.93

C1—P1—C11	101.78 (12)	C17—C16—H16	119.3
C1—P1—C21	103.24 (12)	C18—C17—C16	121.6 (2)
C11—P1—C21	102.27 (12)	C18—C17—C12	119.5 (3)
C10—C1—C2	119.1 (3)	C16—C17—C12	118.8 (2)
C10—C1—P1	122.4 (2)	C19—C18—C17	121.0 (3)
C2—C1—P1	118.48 (19)	C19—C18—H18	119.5
C3—C2—C7	118.5 (3)	C17—C18—H18	119.5
C3—C2—C1	122.8 (2)	C18—C19—C20	119.9 (3)
C7—C2—C1	118.7 (2)	C18—C19—H19	120.1
C4—C3—C2	121.0 (3)	C20—C19—H19	120.1
C4—C3—H3	119.5	C11—C20—C19	121.7 (3)
C2—C3—H3	119.5	C11—C20—H20	119.2
C3—C4—C5	120.3 (3)	C19—C20—H20	119.2
C3—C4—H4	119.9	C22—C21—C30	119.0 (2)
C5—C4—H4	119.9	C22—C21—P1	122.43 (19)
C6—C5—C4	120.1 (3)	C30—C21—P1	118.32 (19)
C6—C5—H5	119.9	C21—C22—C23	121.9 (2)
C4—C5—H5	119.9	C21—C22—H22	119.1
C5—C6—C7	121.5 (3)	C23—C22—H22	119.1
C5—C6—H6	119.3	C24—C23—C22	120.4 (3)
C7—C6—H6	119.3	C24—C23—H23	119.8
C6—C7—C8	122.2 (3)	C22—C23—H23	119.8
C6—C7—C2	118.6 (3)	C23—C24—C25	120.5 (2)
C8—C7—C2	119.3 (3)	C23—C24—H24	119.7
C9—C8—C7	121.1 (3)	C25—C24—H24	119.7
C9—C8—H8	119.4	C26—C25—C24	121.4 (2)
C7—C8—H8	119.4	C26—C25—C30	119.0 (3)
C8—C9—C10	120.0 (3)	C24—C25—C30	119.6 (2)
C8—C9—H9	120	C27—C26—C25	121.3 (2)
C10—C9—H9	120	C27—C26—H26	119.3
C1—C10—C9	121.8 (3)	C25—C26—H26	119.3
C1—C10—H10	119.1	C26—C27—C28	119.6 (3)
C9—C10—H10	119.1	C26—C27—H27	120.2
C20—C11—C12	119.1 (2)	C28—C27—H27	120.2
C20—C11—P1	122.3 (2)	C29—C28—C27	120.7 (3)
C12—C11—P1	118.63 (19)	C29—C28—H28	119.6
C13—C12—C17	118.2 (2)	C27—C28—H28	119.6
C13—C12—C11	123.0 (2)	C28—C29—C30	121.1 (2)
C17—C12—C11	118.9 (2)	C28—C29—H29	119.4
C14—C13—C12	121.0 (2)	C30—C29—H29	119.4
C14—C13—H13	119.5	C29—C30—C25	118.2 (2)
C12—C13—H13	119.5	C29—C30—C21	123.2 (2)
C13—C14—C15	120.6 (3)	C25—C30—C21	118.6 (2)
C13—C14—H14	119.7	Cl2—C31—Cl3	111.1 (4)
C15—C14—H14	119.7	Cl2—C31—Cl1	109.0 (4)
C16—C15—C14	119.9 (3)	Cl3—C31—Cl1	110.3 (3)
C16—C15—H15	120.1	Cl2—C31—H31	108.8
C14—C15—H15	120.1	Cl3—C31—H31	108.8
C15—C16—C17	121.5 (3)	Cl1—C31—H31	108.8
C15—C16—H16	119.3

C11—P1—C1—C10	−95.6 (2)	C15—C16—C17—C18	−178.1 (3)
C21—P1—C1—C10	10.2 (3)	C15—C16—C17—C12	0.5 (4)
C11—P1—C1—C2	86.3 (2)	C13—C12—C17—C18	178.9 (2)
C21—P1—C1—C2	−167.9 (2)	C11—C12—C17—C18	−0.3 (3)
C10—C1—C2—C3	−179.1 (3)	C13—C12—C17—C16	0.2 (3)
P1—C1—C2—C3	−0.9 (3)	C11—C12—C17—C16	−178.9 (2)
C10—C1—C2—C7	1.0 (4)	C16—C17—C18—C19	178.6 (2)
P1—C1—C2—C7	179.2 (2)	C12—C17—C18—C19	0.0 (4)
C7—C2—C3—C4	−1.9 (4)	C17—C18—C19—C20	0.3 (4)
C1—C2—C3—C4	178.2 (3)	C12—C11—C20—C19	0.0 (4)
C2—C3—C4—C5	1.4 (4)	P1—C11—C20—C19	−178.18 (19)
C3—C4—C5—C6	0.1 (5)	C18—C19—C20—C11	−0.3 (4)
C4—C5—C6—C7	−1.1 (5)	C1—P1—C21—C22	−106.4 (2)
C5—C6—C7—C8	−178.4 (3)	C11—P1—C21—C22	−1.0 (3)
C5—C6—C7—C2	0.6 (5)	C1—P1—C21—C30	79.4 (2)
C3—C2—C7—C6	0.8 (4)	C11—P1—C21—C30	−175.2 (2)
C1—C2—C7—C6	−179.2 (3)	C30—C21—C22—C23	0.5 (4)
C3—C2—C7—C8	179.9 (3)	P1—C21—C22—C23	−173.6 (2)
C1—C2—C7—C8	−0.2 (4)	C21—C22—C23—C24	0.2 (4)
C6—C7—C8—C9	177.9 (3)	C22—C23—C24—C25	−0.8 (4)
C2—C7—C8—C9	−1.2 (4)	C23—C24—C25—C26	−178.7 (2)
C7—C8—C9—C10	1.6 (5)	C23—C24—C25—C30	0.6 (4)
C2—C1—C10—C9	−0.6 (4)	C24—C25—C26—C27	179.6 (3)
P1—C1—C10—C9	−178.7 (2)	C30—C25—C26—C27	0.3 (4)
C8—C9—C10—C1	−0.7 (5)	C25—C26—C27—C28	−0.4 (4)
C1—P1—C11—C20	9.3 (2)	C26—C27—C28—C29	0.5 (4)
C21—P1—C11—C20	−97.2 (2)	C27—C28—C29—C30	−0.6 (5)
C1—P1—C11—C12	−168.88 (18)	C28—C29—C30—C25	0.5 (4)
C21—P1—C11—C12	84.6 (2)	C28—C29—C30—C21	−179.3 (3)
C20—C11—C12—C13	−178.8 (2)	C26—C25—C30—C29	−0.4 (4)
P1—C11—C12—C13	−0.6 (3)	C24—C25—C30—C29	−179.7 (3)
C20—C11—C12—C17	0.2 (3)	C26—C25—C30—C21	179.4 (2)
P1—C11—C12—C17	178.53 (17)	C24—C25—C30—C21	0.1 (4)
C17—C12—C13—C14	−1.0 (4)	C22—C21—C30—C29	179.1 (3)
C11—C12—C13—C14	178.1 (2)	P1—C21—C30—C29	−6.5 (4)
C12—C13—C14—C15	1.0 (4)	C22—C21—C30—C25	−0.6 (4)
C13—C14—C15—C16	−0.2 (4)	P1—C21—C30—C25	173.73 (19)
C14—C15—C16—C17	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cl1ⁱ	0.93	2.82	3.512 (4)	132
C18—H18···Cg1ⁱⁱ	0.93	2.66	3.579 (3)	170
C24—H24···Cg2ⁱⁱⁱ	0.93	2.51	3.425 (3)	167
C27—H27···Cg2^iv	0.93	2.69	3.612 (3)	170
C8—H8···Cg3^v	0.93	2.79	3.580 (3)	143
C31—H31···Cg4^vi	0.98	2.65	3.618 (6)	172

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C2–C7, C12–C17, C25–C30 and C1/C2/C7–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cl1ⁱ	0.93	2.82	3.512 (4)	132
C18—H18⋯Cg1ⁱⁱ	0.93	2.66	3.579 (3)	170
C24—H24⋯Cg2ⁱⁱⁱ	0.93	2.51	3.425 (3)	167
C27—H27⋯Cg2^iv	0.93	2.69	3.612 (3)	170
C8—H8⋯Cg3^v	0.93	2.79	3.580 (3)	143
C31—H31⋯Cg4^vi	0.98	2.65	3.618 (6)	172

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

3 in total

Tris(naphthalen-1-yl)phosphane chloro-form hemisolvate.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. trans-Chloro(methyl)bis(tricyclohexylphosphine)platinum(II).

2. A short history of SHELX.

3. Rapid phosphorus(III) ligand evaluation utilising potassium selenocyanate.