{2-[tert-But­yl(pyridin-2-yl)phosphino]phen­yl}diphenyl­phosphine

Görl, J.; Razzaq, R.; Spannenberg, A.; Jackstell, R.

doi:10.1107/S2414314626007844

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 8| August 2026| x260784

https://doi.org/10.1107/S2414314626007844

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{2-[tert-Butyl(pyridin-2-yl)phosphino]phenyl}diphenylphosphine

Joseph Görl,^a Rauf Razzaq,^b ^* Anke Spannenberg ^b and Ralf Jackstell ^b

^aRWTH Aachen University, Institute of Technical and Macromolecular Chemistry, Worringerweg 2, 52074 Aachen, Germany, and ^bLeibniz Institute for Catalysis, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 28 July 2026; accepted 30 July 2026; online 4 August 2026)

The title compound, C₂₇H₂₇NP₂, is a new potential asymmetric P,P,N ligand and consists of a diphenylphosphino and a tert-butyl(pyridin-2-yl)phosphino group bridged by a 1,2-phenylene backbone. The dihedral angles between the central and pendant aromatic rings are 83.07 (6), 85.99 (5) and 82.80 (6)°. In the extended structure, weak C—H⋯π interactions link the molecules.

Keywords: crystal structure; phosphine ligand; P,P,N donor.

CCDC reference: 2578570

Structure description

The title compound, C₂₇H₂₇NP₂, consists of diphenylphosphino and tert-butyl(pyridin-2-yl)phosphino groups bridged by a 1,2-phenylene backbone (Fig. 1). This compound can act as a tridentate P,P,N donor ligand containing two phosphine donors and one pyridyl nitrogen donor. This opens new possibilities for multi-functional ligand and complex design for various chemical transformations in homogeneous catalysis (Breit, 2000 ; Fablet et al., 2024 ) where the steric and electronic properties of the phosphorus ligands strongly influence catalyst performance. In the crystal structure, the steric demand results from the presence of a phenylene backbone. The dihedral angles between the central C10–C15 ring and pendant C1–C5/N1, C16–C21 and C22–C27 rings are 83.07 (6), 85.99 (5) and 82.80 (6)°, respectively. The N1—C1—P1—C10 torsion angle is 108.10 (11)° and two short intramolecular C—H⋯N contacts (Table 1) occur. In the extended structure, some weak C—H⋯π interactions are observed.

Table 1
C—H⋯N contacts and C—H⋯π interactions (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C10–C15, C16–C21 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N1	0.98	2.51	3.1946 (18)	127
C8—H8B⋯N1	0.98	2.48	3.1921 (19)	129
C9—H9B⋯Cg3ⁱ	0.98	2.97	3.8163 (14)	145
C13—H13⋯Cg4ⁱⁱ	0.95	2.85	3.6835 (12)	146
C14—H14⋯Cg3	0.95	2.97	3.7522 (12)	140
C18—H18⋯Cg2ⁱⁱⁱ	0.95	2.71	3.6314 (12)	163
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 1
The molecular structure of the title compound. Displacement ellipsoids correspond to the 50% probability level.

Synthesis and crystallization

The title compound was obtained by dissolving (2-bromophenyl)(tert-butyl)(pyridin-2-yl)phosphine (6.02 g, 18.8 mmol) in 70 ml of tetrahydrofuran (THF) and cooled to 203 K. A 1.6 N solution of n-butyllithium in THF (11.75 ml, 18.8 mmol) was added dropwise without raising the internal temperature of the solution above 213 K. The temperature was maintained, and the reaction mixture was stirred for 45 min. Chlorodiphenylphosphine (4.14 g, 3.46 ml, 18.8 mmol) was added dropwise. The cooling was removed and upon reaching room temperature, the solution was stirred for further 15 min. The solvent was removed in vacuo, leaving behind a brown solid, which was redissolved in a mixture of 40 ml of diethylether and 30 ml of toluene. The solution was washed with 20 ml of distilled water three times and the solvent was removed in vacuo. The resulting solid was crystallized from acetone solution, giving 3.83 g (8.97 mmol, 47.7%) of the product as a crystalline material.

¹H-NMR (300 MHz, CD₂Cl₂): δ = 8.61–8.64 (m, 1 H, H6), 7.66–7.72 (m, 1 H, H4), 7.22–7.40 (m, 13 H, H5, H10, H11, H15–H17) 7.03–7.08 (m, 1 H, H3), 6.95–7.01 (m, 1 H, H9), 6.89–6.95 (m, 1 H, H12), 1.33 (d, ³J_HP = 12.7 Hz, 9 H, 1H) ppm. ¹³C{¹H}-NMR (300 MHz, CD₂Cl₂): δ = 165.40 (dd, ¹J_CP = 11.8 Hz, ⁴J_CP = 7.4 Hz, 1 C, C7), 149.18 (d, ³J_CP = 5.5 Hz, 1 C, C6), 146.88 (dd, ¹J_CP = 35.3 Hz, ²J_CP = 11.2 Hz, 1 C, C8), 142.00 (dd, ¹J_CP = 29.3 Hz, ²J_CP = 15.3 Hz, 1 C, C13), 137.84–138.51 (m, 2 C, C4, C12), 136.35 (dd, ¹J_CP = 4.9 Hz, ⁴J_CP = 2.7 Hz, 2 C, C14), 134.47 (d, ²J_CP = 6.3 Hz, 1 C, C9), 134. 38 (d, ²J_CP = 20.4 Hz, 4 C, C15), 133.76 (d, ³J_CP = 19.2 Hz, 4 C, C16), 133.29 (d, ⁴J_CP = 9.1 Hz, 2 C, C17) 129.62 (d, ³J_CP = 1.6 Hz, 1 C, C10), 129.02 (d, ³J_CP = 29.4 Hz, 1 C, C11), 128.23–128.57 (m, 3 C, C3, C4, C5), 33.20 (dd, ¹J_CP = 15.7 Hz, ⁴J_CP = 2.9 Hz, 1 C, C2), 28.37 (dd, ²J_CP = 12.9 Hz, ⁵J_CP = 2.0 Hz, 3 C, C1) ppm. ³¹P{¹H}-NMR (300 MHz, CD₂Cl₂): δ = 3.06 (d, ³J_PP = 154 Hz, 1 P, R-PPh₂), −9.90 (d, ³J_PP = 154 Hz, 1 P, R—P(tert-butyl)(pyridyl) ppm.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₇H₂₇NP₂
M_r	427.43
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	7.8716 (7), 11.1132 (9), 13.3896 (11)
α, β, γ (°)	91.8079 (18), 100.1759 (17), 97.1105 (17)
V (Å³)	1142.30 (17)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.20
Crystal size (mm)	0.36 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.93, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	67091, 5960, 5557
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.084, 1.05
No. of reflections	5960
No. of parameters	274
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.22
Computer programs: APEX2 (Bruker, 2014 ) and SAINT (Bruker, 2013 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), XP in SHELXTL (Sheldrick, 2008 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2578570

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626007844/hb4567sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626007844/hb4567Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626007844/hb4567Isup3.cml

checkCIF report

Computing details top

{2-[tert-Butyl(pyridin-2-yl)phosphino]phenyl}diphenylphosphine top

Crystal data top

C₂₇H₂₇NP₂	Z = 2
M_r = 427.43	F(000) = 452
Triclinic, P1	D_x = 1.243 Mg m⁻³
a = 7.8716 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1132 (9) Å	Cell parameters from 9606 reflections
c = 13.3896 (11) Å	θ = 2.4–28.8°
α = 91.8079 (18)°	µ = 0.20 mm⁻¹
β = 100.1759 (17)°	T = 150 K
γ = 97.1105 (17)°	Block, colourless
V = 1142.30 (17) Å³	0.36 × 0.30 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	5960 independent reflections
Radiation source: fine-focus sealed tube	5557 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	R_int = 0.020
φ and ω scans	θ_max = 28.8°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
T_min = 0.93, T_max = 0.96	k = −15→15
67091 measured reflections	l = −18→18

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0428P)² + 0.4017P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5960 reflections	Δρ_max = 0.36 e Å⁻³
274 parameters	Δρ_min = −0.22 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.32534 (12)	0.18587 (10)	0.60893 (8)	0.02296 (19)
C2	0.28865 (16)	0.26468 (12)	0.53202 (9)	0.0355 (3)
H2	0.305204	0.349900	0.547051	0.043*
C3	0.22765 (17)	0.21822 (15)	0.43302 (10)	0.0435 (3)
H3	0.205756	0.271065	0.379167	0.052*
C4	0.1995 (2)	0.09449 (16)	0.41425 (10)	0.0505 (4)
H4	0.157672	0.059450	0.347438	0.061*
C5	0.2336 (3)	0.02348 (16)	0.49509 (12)	0.0643 (5)
H5	0.211051	−0.062102	0.482346	0.077*
C6	0.42574 (13)	0.12441 (9)	0.82445 (8)	0.02225 (19)
C7	0.24175 (15)	0.05800 (11)	0.82173 (10)	0.0322 (2)
H7A	0.198835	0.015683	0.755028	0.048*
H7B	0.163842	0.117023	0.833796	0.048*
H7C	0.245172	−0.001085	0.874618	0.048*
C8	0.54692 (16)	0.03401 (10)	0.80124 (10)	0.0321 (2)
H8A	0.664946	0.076579	0.805694	0.048*
H8B	0.505166	−0.003202	0.732548	0.048*
H8C	0.548296	−0.029296	0.850588	0.048*
C9	0.49409 (16)	0.18470 (11)	0.93116 (8)	0.0306 (2)
H9A	0.503670	0.122008	0.980971	0.046*
H9B	0.413300	0.239414	0.947727	0.046*
H9C	0.608924	0.231152	0.932890	0.046*
C10	0.62729 (12)	0.31172 (8)	0.72764 (7)	0.01762 (17)
C11	0.72339 (13)	0.24493 (9)	0.67294 (8)	0.02238 (19)
H11	0.671746	0.168114	0.641456	0.027*
C12	0.89277 (13)	0.28873 (10)	0.66378 (8)	0.0257 (2)
H12	0.957337	0.241007	0.628230	0.031*
C13	0.96706 (13)	0.40239 (10)	0.70676 (8)	0.0255 (2)
H13	1.082170	0.433398	0.699877	0.031*
C14	0.87267 (13)	0.47082 (9)	0.75992 (8)	0.02235 (19)
H14	0.923905	0.549081	0.788404	0.027*
C15	0.70346 (12)	0.42681 (8)	0.77241 (7)	0.01798 (17)
C16	0.74811 (13)	0.63927 (9)	0.90193 (7)	0.02054 (18)
C17	0.86099 (14)	0.62644 (9)	0.99293 (8)	0.0260 (2)
H17	0.847739	0.553460	1.027483	0.031*
C18	0.99244 (15)	0.71938 (10)	1.03341 (8)	0.0292 (2)
H18	1.069724	0.709009	1.094633	0.035*
C19	1.01101 (14)	0.82715 (10)	0.98463 (8)	0.0267 (2)
H19	1.101408	0.890384	1.012042	0.032*
C20	0.89724 (13)	0.84230 (9)	0.89577 (8)	0.0243 (2)
H20	0.908366	0.916664	0.862933	0.029*
C21	0.76681 (13)	0.74904 (9)	0.85447 (8)	0.02204 (18)
H21	0.689654	0.760101	0.793373	0.026*
C22	0.43871 (12)	0.58380 (9)	0.75901 (8)	0.02325 (19)
C23	0.32287 (14)	0.65208 (10)	0.79593 (10)	0.0318 (2)
H23	0.320156	0.656429	0.866595	0.038*
C24	0.21165 (16)	0.71362 (11)	0.72955 (13)	0.0421 (3)
H24	0.135332	0.761420	0.755295	0.051*
C25	0.21165 (18)	0.70561 (14)	0.62686 (14)	0.0490 (4)
H25	0.134293	0.746912	0.581786	0.059*
C26	0.32416 (19)	0.63748 (15)	0.58911 (12)	0.0466 (3)
H26	0.323595	0.631456	0.518116	0.056*
C27	0.43830 (15)	0.57773 (11)	0.65544 (9)	0.0314 (2)
H27	0.516850	0.532247	0.629354	0.038*
N1	0.2969 (2)	0.06600 (11)	0.59120 (9)	0.0481 (3)
P1	0.40197 (3)	0.25420 (2)	0.73905 (2)	0.01760 (7)
P2	0.58338 (3)	0.50958 (2)	0.85282 (2)	0.02000 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0170 (4)	0.0292 (5)	0.0219 (4)	0.0007 (3)	0.0037 (3)	−0.0027 (4)
C2	0.0340 (6)	0.0415 (6)	0.0275 (5)	0.0010 (5)	−0.0010 (4)	0.0031 (5)
C3	0.0338 (6)	0.0691 (9)	0.0245 (5)	0.0012 (6)	0.0005 (5)	0.0047 (6)
C4	0.0488 (8)	0.0720 (10)	0.0246 (6)	−0.0073 (7)	0.0038 (5)	−0.0143 (6)
C5	0.1049 (15)	0.0445 (8)	0.0351 (7)	−0.0106 (9)	0.0079 (8)	−0.0178 (6)
C6	0.0239 (4)	0.0193 (4)	0.0244 (4)	0.0020 (3)	0.0070 (4)	0.0030 (3)
C7	0.0307 (5)	0.0271 (5)	0.0391 (6)	−0.0048 (4)	0.0125 (5)	0.0038 (4)
C8	0.0374 (6)	0.0245 (5)	0.0391 (6)	0.0122 (4)	0.0127 (5)	0.0077 (4)
C9	0.0386 (6)	0.0303 (5)	0.0221 (5)	0.0029 (4)	0.0039 (4)	0.0043 (4)
C10	0.0160 (4)	0.0183 (4)	0.0183 (4)	0.0020 (3)	0.0026 (3)	0.0012 (3)
C11	0.0206 (4)	0.0219 (4)	0.0245 (4)	0.0020 (3)	0.0050 (3)	−0.0034 (4)
C12	0.0204 (4)	0.0289 (5)	0.0290 (5)	0.0042 (4)	0.0082 (4)	−0.0045 (4)
C13	0.0171 (4)	0.0284 (5)	0.0311 (5)	0.0005 (4)	0.0070 (4)	−0.0009 (4)
C14	0.0191 (4)	0.0200 (4)	0.0273 (5)	−0.0004 (3)	0.0049 (4)	−0.0002 (4)
C15	0.0179 (4)	0.0176 (4)	0.0189 (4)	0.0032 (3)	0.0037 (3)	0.0019 (3)
C16	0.0212 (4)	0.0182 (4)	0.0225 (4)	0.0028 (3)	0.0049 (3)	−0.0022 (3)
C17	0.0290 (5)	0.0216 (5)	0.0269 (5)	0.0051 (4)	0.0016 (4)	0.0029 (4)
C18	0.0282 (5)	0.0293 (5)	0.0269 (5)	0.0045 (4)	−0.0038 (4)	0.0005 (4)
C19	0.0240 (5)	0.0248 (5)	0.0285 (5)	−0.0003 (4)	0.0005 (4)	−0.0042 (4)
C20	0.0259 (5)	0.0190 (4)	0.0270 (5)	0.0005 (4)	0.0036 (4)	0.0005 (4)
C21	0.0225 (4)	0.0207 (4)	0.0219 (4)	0.0017 (3)	0.0023 (3)	−0.0002 (3)
C22	0.0176 (4)	0.0168 (4)	0.0348 (5)	0.0006 (3)	0.0044 (4)	−0.0001 (4)
C23	0.0213 (5)	0.0234 (5)	0.0499 (7)	0.0020 (4)	0.0068 (4)	−0.0078 (5)
C24	0.0239 (5)	0.0244 (5)	0.0795 (10)	0.0079 (4)	0.0104 (6)	0.0029 (6)
C25	0.0319 (6)	0.0448 (7)	0.0752 (10)	0.0170 (6)	0.0103 (6)	0.0294 (7)
C26	0.0389 (7)	0.0583 (9)	0.0474 (8)	0.0186 (6)	0.0084 (6)	0.0263 (7)
C27	0.0274 (5)	0.0338 (6)	0.0356 (6)	0.0103 (4)	0.0077 (4)	0.0098 (5)
N1	0.0792 (9)	0.0311 (5)	0.0293 (5)	−0.0018 (5)	0.0048 (5)	−0.0086 (4)
P1	0.01578 (11)	0.01752 (11)	0.01963 (12)	0.00196 (8)	0.00391 (8)	−0.00018 (8)
P2	0.02038 (12)	0.01672 (12)	0.02347 (12)	0.00125 (9)	0.00671 (9)	−0.00103 (9)

Geometric parameters (Å, º) top

C1—N1	1.3299 (15)	C12—H12	0.9500
C1—C2	1.3876 (16)	C13—C14	1.3891 (14)
C1—P1	1.8461 (10)	C13—H13	0.9500
C2—C3	1.3873 (17)	C14—C15	1.4014 (13)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.373 (2)	C15—P2	1.8469 (10)
C3—H3	0.9500	C16—C21	1.3969 (14)
C4—C5	1.368 (2)	C16—C17	1.3979 (14)
C4—H4	0.9500	C16—P2	1.8349 (10)
C5—N1	1.3432 (18)	C17—C18	1.3904 (15)
C5—H5	0.9500	C17—H17	0.9500
C6—C8	1.5291 (14)	C18—C19	1.3864 (16)
C6—C7	1.5358 (15)	C18—H18	0.9500
C6—C9	1.5359 (15)	C19—C20	1.3855 (15)
C6—P1	1.8756 (10)	C19—H19	0.9500
C7—H7A	0.9800	C20—C21	1.3906 (14)
C7—H7B	0.9800	C20—H20	0.9500
C7—H7C	0.9800	C21—H21	0.9500
C8—H8A	0.9800	C22—C27	1.3857 (16)
C8—H8B	0.9800	C22—C23	1.3995 (14)
C8—H8C	0.9800	C22—P2	1.8295 (11)
C9—H9A	0.9800	C23—C24	1.3914 (18)
C9—H9B	0.9800	C23—H23	0.9500
C9—H9C	0.9800	C24—C25	1.375 (2)
C10—C11	1.4000 (13)	C24—H24	0.9500
C10—C15	1.4105 (13)	C25—C26	1.383 (2)
C10—P1	1.8436 (9)	C25—H25	0.9500
C11—C12	1.3895 (14)	C26—C27	1.3928 (16)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.3860 (15)	C27—H27	0.9500

N1—C1—C2	121.73 (10)	C14—C13—H13	120.1
N1—C1—P1	121.06 (9)	C13—C14—C15	121.38 (9)
C2—C1—P1	117.09 (8)	C13—C14—H14	119.3
C3—C2—C1	119.56 (13)	C15—C14—H14	119.3
C3—C2—H2	120.2	C14—C15—C10	118.75 (8)
C1—C2—H2	120.2	C14—C15—P2	122.13 (7)
C4—C3—C2	118.84 (13)	C10—C15—P2	118.97 (7)
C4—C3—H3	120.6	C21—C16—C17	118.46 (9)
C2—C3—H3	120.6	C21—C16—P2	124.21 (8)
C5—C4—C3	117.68 (12)	C17—C16—P2	117.33 (8)
C5—C4—H4	121.2	C18—C17—C16	120.69 (10)
C3—C4—H4	121.2	C18—C17—H17	119.7
N1—C5—C4	124.73 (15)	C16—C17—H17	119.7
N1—C5—H5	117.6	C19—C18—C17	120.16 (10)
C4—C5—H5	117.6	C19—C18—H18	119.9
C8—C6—C7	110.00 (9)	C17—C18—H18	119.9
C8—C6—C9	109.28 (9)	C20—C19—C18	119.76 (10)
C7—C6—C9	108.63 (9)	C20—C19—H19	120.1
C8—C6—P1	117.08 (7)	C18—C19—H19	120.1
C7—C6—P1	106.73 (7)	C19—C20—C21	120.23 (10)
C9—C6—P1	104.75 (7)	C19—C20—H20	119.9
C6—C7—H7A	109.5	C21—C20—H20	119.9
C6—C7—H7B	109.5	C20—C21—C16	120.66 (9)
H7A—C7—H7B	109.5	C20—C21—H21	119.7
C6—C7—H7C	109.5	C16—C21—H21	119.7
H7A—C7—H7C	109.5	C27—C22—C23	118.65 (10)
H7B—C7—H7C	109.5	C27—C22—P2	124.46 (8)
C6—C8—H8A	109.5	C23—C22—P2	116.88 (9)
C6—C8—H8B	109.5	C24—C23—C22	120.26 (12)
H8A—C8—H8B	109.5	C24—C23—H23	119.9
C6—C8—H8C	109.5	C22—C23—H23	119.9
H8A—C8—H8C	109.5	C25—C24—C23	120.33 (12)
H8B—C8—H8C	109.5	C25—C24—H24	119.8
C6—C9—H9A	109.5	C23—C24—H24	119.8
C6—C9—H9B	109.5	C24—C25—C26	120.07 (12)
H9A—C9—H9B	109.5	C24—C25—H25	120.0
C6—C9—H9C	109.5	C26—C25—H25	120.0
H9A—C9—H9C	109.5	C25—C26—C27	119.83 (14)
H9B—C9—H9C	109.5	C25—C26—H26	120.1
C11—C10—C15	119.04 (8)	C27—C26—H26	120.1
C11—C10—P1	121.36 (7)	C22—C27—C26	120.84 (11)
C15—C10—P1	119.58 (7)	C22—C27—H27	119.6
C12—C11—C10	121.32 (9)	C26—C27—H27	119.6
C12—C11—H11	119.3	C1—N1—C5	117.39 (13)
C10—C11—H11	119.3	C10—P1—C1	98.68 (4)
C13—C12—C11	119.68 (9)	C10—P1—C6	104.17 (4)
C13—C12—H12	120.2	C1—P1—C6	106.31 (5)
C11—C12—H12	120.2	C22—P2—C16	100.00 (4)
C12—C13—C14	119.79 (9)	C22—P2—C15	102.38 (5)
C12—C13—H13	120.1	C16—P2—C15	100.61 (4)

N1—C1—C2—C3	−2.81 (19)	C25—C26—C27—C22	1.1 (2)
P1—C1—C2—C3	−178.86 (10)	C2—C1—N1—C5	1.1 (2)
C1—C2—C3—C4	2.2 (2)	P1—C1—N1—C5	177.03 (14)
C2—C3—C4—C5	0.0 (2)	C4—C5—N1—C1	1.2 (3)
C3—C4—C5—N1	−1.7 (3)	C11—C10—P1—C1	−38.87 (9)
C15—C10—C11—C12	1.31 (15)	C15—C10—P1—C1	139.35 (8)
P1—C10—C11—C12	179.54 (8)	C11—C10—P1—C6	70.49 (9)
C10—C11—C12—C13	−2.04 (16)	C15—C10—P1—C6	−111.29 (8)
C11—C12—C13—C14	0.97 (16)	N1—C1—P1—C10	108.10 (11)
C12—C13—C14—C15	0.82 (16)	C2—C1—P1—C10	−75.83 (9)
C13—C14—C15—C10	−1.53 (15)	N1—C1—P1—C6	0.48 (11)
C13—C14—C15—P2	174.09 (8)	C2—C1—P1—C6	176.56 (8)
C11—C10—C15—C14	0.46 (14)	C8—C6—P1—C10	−46.32 (9)
P1—C10—C15—C14	−177.80 (7)	C7—C6—P1—C10	−170.02 (7)
C11—C10—C15—P2	−175.29 (7)	C9—C6—P1—C10	74.89 (8)
P1—C10—C15—P2	6.44 (10)	C8—C6—P1—C1	57.33 (9)
C21—C16—C17—C18	−2.10 (15)	C7—C6—P1—C1	−66.37 (8)
P2—C16—C17—C18	178.12 (8)	C9—C6—P1—C1	178.54 (7)
C16—C17—C18—C19	1.18 (17)	C27—C22—P2—C16	100.31 (10)
C17—C18—C19—C20	0.49 (17)	C23—C22—P2—C16	−78.92 (8)
C18—C19—C20—C21	−1.20 (16)	C27—C22—P2—C15	−3.00 (10)
C19—C20—C21—C16	0.24 (16)	C23—C22—P2—C15	177.77 (8)
C17—C16—C21—C20	1.39 (15)	C21—C16—P2—C22	−14.73 (9)
P2—C16—C21—C20	−178.85 (8)	C17—C16—P2—C22	165.04 (8)
C27—C22—C23—C24	−0.84 (16)	C21—C16—P2—C15	90.02 (9)
P2—C22—C23—C24	178.44 (9)	C17—C16—P2—C15	−90.22 (8)
C22—C23—C24—C25	1.53 (18)	C14—C15—P2—C22	100.67 (8)
C23—C24—C25—C26	−0.9 (2)	C10—C15—P2—C22	−83.73 (8)
C24—C25—C26—C27	−0.5 (2)	C14—C15—P2—C16	−2.16 (9)
C23—C22—C27—C26	−0.49 (18)	C10—C15—P2—C16	173.44 (7)
P2—C22—C27—C26	−179.71 (10)

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3 and Cg4 are the centroids of the C10–C15, C16–C21 and C22–C27 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N1	0.98	2.51	3.1946 (18)	127
C8—H8B···N1	0.98	2.48	3.1921 (19)	129
C9—H9B···Cg3ⁱ	0.98	2.97	3.8163 (14)	145
C13—H13···Cg4ⁱⁱ	0.95	2.85	3.6835 (12)	146
C14—H14···Cg3	0.95	2.97	3.7522 (12)	140
C18—H18···Cg2ⁱⁱⁱ	0.95	2.71	3.6314 (12)	163

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z; (iii) −x+2, −y+1, −z+2.

References

Breit, B. (2000). Acc. Chem. Res. 33, 353–360. Google Scholar
Bruker (2013). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2014). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fablet, P., Fernandez-Martinez, M. D., Spannenberg, A., Jiao, H., Jackstell, R. & Beller, M. (2024). Org. Biomol. Chem. 22, 5850–5855. CrossRef CAS PubMed Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 11| Part 8| August 2026| x260784

https://doi.org/10.1107/S2414314626007844

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{2-[tert-But­yl(pyridin-2-yl)phosphino]phen­yl}di­phenyl­phosphine

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

{2-[tert-Butyl(pyridin-2-yl)phosphino]phenyl}diphenylphosphine