1-Phenyl-4-(triphenyl­phosphanyl­idene)pyrrolidine-2,3,5-trione

Fan, D.-H.

doi:10.1107/S1600536808003565

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o570

doi:10.1107/S1600536808003565

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1-Phenyl-4-(triphenylphosphanylidene)pyrrolidine-2,3,5-trione

Da-He Fan ^a ^*

^aSchool of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng 224003, People's Republic of China
^*Correspondence e-mail: shenyongmiao@zscas.edu.cn

(Received 26 December 2007; accepted 1 February 2008; online 8 February 2008)

In the title compound, C₂₈H₂₀NO₃P, the five-membered maleimide ring is almost planar. The interplanar angles between the maleimide ring and the three P-bound phenyl rings are 70.6 (2), 60.4 (2) and 54.68 (18)°, while the dihedral angle between the maleimide ring and the N-bound phenyl group is 55.43 (19)°.

Related literature

For related literature, see: Augustin et al. (1979 ); Trost & Schmidt (1988 ); Mao et al. (2005 ).

Experimental

Crystal data

C₂₈H₂₀NO₃P
M_r = 449.42
Orthorhombic, P b c a
a = 18.171 (4) Å
b = 12.553 (3) Å
c = 19.982 (4) Å
V = 4557.9 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 ) T_min = 0.956, T_max = 0.970
3961 measured reflections
3961 independent reflections
2590 reflections with I > 2σ(I)
3 standard reflections every 150 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.180
S = 1.07
3961 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003565/tk2239sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003565/tk2239Isup2.hkl

checkCIF report

Comment top

Organophosphorus compounds play an important role in organic synthesis. In some reactions, a nucleophilic tertiary phosphine initially adds to the triple bond of an electron-deficient alkyne and is finally eliminated from the reaction product after a series of transformations. As such, the tertiary phosphine plays the role of a catalyst (Trost et al., 1988). In recent experiments, the title compound, (I), was synthesized unexpectedly when triphenylphosphine, Ph₃P, was used as a catalyst in a reaction with N-phenylmaleimide (Augustin et al., 1979). In this reaction, the Ph₃P was not eliminated but instead reacted (Mao et al., 2005). The stucture of (I), Fig. 1, shows the interplanar angles between the maleimide ring and the three P-bound phenyl rings to be 70.6 (2), 60.4 (2) and 54.68 (18)°, respectively, and the dihedral angle between the maleimide ring and the N-bound phenyl group to be 55.4 (3)°.

Related literature top

For related literature, see: Augustin et al. (1979); Trost & Schmidt (1988); Mao et al. (2005).

Experimental top

To a CH₂Cl₂ (5 ml) solution comprising Ph₃P (0.06 g, 0.00014 mmol), N-phenylmaleimide (0.173 g, 1.0 mmol) and 1-aminobenzotriazole (0.201 g, 1.5 mmol), lead tetraacetate (0.666 g, 1.5 mmol) in CH₂Cl₂ (5 ml) was added dropwise. After stirring at room temperature for 30 min, the solution was concentrated and separated by flash chromatography on a silica gel column with petroleum ether/ethyl acetate as eluent. Compound (I) was isolated as one of the products (yield 2.4%); m. pt. 526 K.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom labelling scheme.

1-Phenyl-4-(triphenylphosphanylidene)pyrrolidine-2,3,5-trione top

Crystal data top

C₂₈H₂₀NO₃P	D_x = 1.310 Mg m⁻³
M_r = 449.42	Melting point: 527 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 187 reflections
a = 18.171 (4) Å	θ = 3.6–45.0°
b = 12.553 (3) Å	µ = 0.15 mm⁻¹
c = 19.982 (4) Å	T = 293 K
V = 4557.9 (16) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.20 mm
F(000) = 1872

Data collection top

Enraf–Nonius CAD-4 diffractometer	2590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω/2θ scans	h = 0→21
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = 0→14
T_min = 0.956, T_max = 0.970	l = −23→0
3961 measured reflections	3 standard reflections every 150 reflections
3961 independent reflections	intensity decay: none

Refinement top

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.180	w = 1/[σ²(F_o²) + (0.0776P)² + 4.6891P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3961 reflections	Δρ_max = 0.40 e Å⁻³
299 parameters	Δρ_min = −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: 0.0079 (7)

Crystal data top

C₂₈H₂₀NO₃P	V = 4557.9 (16) Å³
M_r = 449.42	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.171 (4) Å	µ = 0.15 mm⁻¹
b = 12.553 (3) Å	T = 293 K
c = 19.982 (4) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2590 reflections with I > 2σ(I)
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	R_int = 0.000
T_min = 0.956, T_max = 0.970	3 standard reflections every 150 reflections
3961 measured reflections	intensity decay: none
3961 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.07	Δρ_max = 0.40 e Å⁻³
3961 reflections	Δρ_min = −0.34 e Å⁻³
299 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.14772 (19)	0.5354 (3)	0.47338 (17)	0.0463 (9)
C2	0.14220 (18)	0.6388 (3)	0.43154 (16)	0.0420 (8)
C3	0.10163 (18)	0.6110 (3)	0.37341 (15)	0.0377 (8)
C4	0.07940 (18)	0.5005 (3)	0.37848 (16)	0.0408 (8)
C5	0.0969 (2)	0.3513 (3)	0.46274 (16)	0.0436 (8)
C6	0.0270 (2)	0.3128 (3)	0.46980 (19)	0.0532 (10)
H6A	−0.0131	0.3545	0.4577	0.064*
C7	0.0162 (3)	0.2110 (3)	0.4952 (2)	0.0619 (11)
H7A	−0.0313	0.1845	0.5003	0.074*
C8	0.0757 (3)	0.1496 (3)	0.5128 (2)	0.0647 (11)
H8A	0.0686	0.0816	0.5301	0.078*
C9	0.1461 (3)	0.1888 (3)	0.5048 (2)	0.0645 (11)
H9A	0.1863	0.1470	0.5166	0.077*
C10	0.1572 (2)	0.2895 (3)	0.47953 (19)	0.0516 (9)
H10A	0.2046	0.3157	0.4738	0.062*
C11	0.1025 (2)	0.8272 (3)	0.32675 (17)	0.0448 (8)
C12	0.0544 (3)	0.9069 (3)	0.3436 (2)	0.0627 (11)
H12A	0.0041	0.8933	0.3448	0.075*
C13	0.0807 (4)	1.0078 (4)	0.3588 (3)	0.0909 (17)
H13A	0.0483	1.0624	0.3696	0.109*
C14	0.1563 (4)	1.0261 (4)	0.3575 (3)	0.0956 (18)
H14A	0.1744	1.0932	0.3685	0.115*
C15	0.2036 (3)	0.9482 (4)	0.3407 (2)	0.0782 (14)
H15A	0.2538	0.9621	0.3394	0.094*
C16	0.1779 (2)	0.8478 (4)	0.3253 (2)	0.0607 (11)
H16A	0.2108	0.7939	0.3140	0.073*
C17	−0.02614 (17)	0.6940 (3)	0.30122 (16)	0.0388 (8)
C18	−0.07044 (19)	0.6465 (3)	0.34892 (18)	0.0513 (9)
H18A	−0.0492	0.6132	0.3858	0.062*
C19	−0.1459 (2)	0.6482 (4)	0.3422 (2)	0.0695 (13)
H19A	−0.1755	0.6137	0.3733	0.083*
C20	−0.1774 (2)	0.7013 (4)	0.2891 (2)	0.0678 (12)
H20A	−0.2284	0.7045	0.2854	0.081*
C21	−0.1342 (2)	0.7497 (4)	0.2415 (2)	0.0635 (11)
H21A	−0.1560	0.7850	0.2057	0.076*
C22	−0.05895 (19)	0.7460 (3)	0.24670 (19)	0.0520 (9)
H22A	−0.0297	0.7779	0.2142	0.062*
C23	0.11017 (17)	0.6596 (3)	0.22757 (16)	0.0404 (8)
C24	0.1195 (2)	0.7381 (4)	0.17908 (19)	0.0568 (10)
H24A	0.1071	0.8084	0.1885	0.068*
C25	0.1475 (2)	0.7109 (4)	0.11636 (19)	0.0642 (12)
H25A	0.1540	0.7631	0.0839	0.077*
C26	0.1653 (2)	0.6068 (5)	0.1026 (2)	0.0694 (13)
H26A	0.1839	0.5886	0.0607	0.083*
C27	0.1559 (2)	0.5302 (4)	0.1501 (2)	0.0667 (12)
H27A	0.1681	0.4600	0.1403	0.080*
C28	0.1284 (2)	0.5556 (3)	0.21299 (19)	0.0536 (10)
H28A	0.1224	0.5027	0.2451	0.064*
N1	0.10879 (16)	0.4592 (2)	0.43984 (14)	0.0445 (7)
O1	0.17921 (16)	0.5257 (2)	0.52663 (13)	0.0717 (9)
O2	0.16942 (15)	0.7217 (2)	0.45206 (13)	0.0610 (8)
O3	0.04234 (15)	0.4470 (2)	0.34108 (12)	0.0568 (7)
P	0.07209 (4)	0.69405 (7)	0.30865 (4)	0.0358 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0449 (19)	0.056 (2)	0.0382 (19)	0.0003 (17)	−0.0043 (16)	−0.0005 (17)
C2	0.0376 (17)	0.052 (2)	0.0361 (18)	0.0013 (16)	−0.0016 (15)	−0.0003 (16)
C3	0.0375 (17)	0.0408 (19)	0.0348 (17)	0.0025 (15)	−0.0036 (14)	−0.0018 (14)
C4	0.0430 (19)	0.045 (2)	0.0341 (17)	0.0074 (16)	−0.0041 (15)	−0.0012 (15)
C5	0.051 (2)	0.045 (2)	0.0353 (18)	0.0036 (17)	0.0005 (15)	0.0006 (15)
C6	0.053 (2)	0.055 (2)	0.052 (2)	0.0084 (19)	−0.0034 (18)	0.0045 (18)
C7	0.071 (3)	0.056 (3)	0.059 (2)	−0.010 (2)	0.000 (2)	0.007 (2)
C8	0.086 (3)	0.044 (2)	0.064 (3)	0.005 (2)	0.001 (2)	0.009 (2)
C9	0.077 (3)	0.056 (3)	0.061 (3)	0.021 (2)	0.001 (2)	0.010 (2)
C10	0.048 (2)	0.053 (2)	0.054 (2)	0.0111 (17)	0.0017 (17)	0.0042 (18)
C11	0.049 (2)	0.048 (2)	0.0376 (18)	−0.0043 (17)	0.0016 (15)	0.0031 (15)
C12	0.073 (3)	0.050 (2)	0.064 (3)	0.005 (2)	0.004 (2)	−0.007 (2)
C13	0.120 (5)	0.050 (3)	0.102 (4)	0.004 (3)	0.016 (3)	−0.016 (3)
C14	0.141 (6)	0.056 (3)	0.090 (4)	−0.035 (4)	−0.009 (4)	−0.009 (3)
C15	0.089 (4)	0.077 (3)	0.069 (3)	−0.040 (3)	0.004 (3)	−0.004 (3)
C16	0.053 (2)	0.065 (3)	0.064 (3)	−0.015 (2)	0.0049 (19)	−0.003 (2)
C17	0.0333 (17)	0.0425 (18)	0.0404 (18)	0.0039 (15)	−0.0031 (14)	−0.0014 (15)
C18	0.0388 (19)	0.075 (3)	0.0404 (19)	−0.0013 (18)	0.0010 (16)	0.0088 (18)
C19	0.043 (2)	0.108 (4)	0.057 (2)	−0.007 (2)	0.0007 (19)	0.017 (2)
C20	0.033 (2)	0.100 (4)	0.070 (3)	0.004 (2)	0.0008 (19)	0.012 (3)
C21	0.042 (2)	0.077 (3)	0.072 (3)	0.003 (2)	−0.010 (2)	0.021 (2)
C22	0.0396 (19)	0.062 (2)	0.055 (2)	0.0029 (18)	−0.0015 (17)	0.0202 (19)
C23	0.0318 (16)	0.056 (2)	0.0334 (17)	−0.0008 (16)	−0.0025 (14)	−0.0026 (15)
C24	0.049 (2)	0.074 (3)	0.047 (2)	0.006 (2)	−0.0005 (17)	0.009 (2)
C25	0.053 (2)	0.106 (4)	0.034 (2)	0.004 (2)	−0.0038 (17)	0.012 (2)
C26	0.052 (2)	0.118 (4)	0.038 (2)	−0.009 (3)	0.0076 (18)	−0.018 (3)
C27	0.069 (3)	0.081 (3)	0.050 (2)	−0.002 (2)	0.008 (2)	−0.025 (2)
C28	0.053 (2)	0.065 (3)	0.043 (2)	−0.0003 (19)	0.0045 (17)	−0.0066 (18)
N1	0.0512 (17)	0.0441 (17)	0.0382 (15)	0.0040 (14)	−0.0062 (13)	0.0036 (13)
O1	0.087 (2)	0.075 (2)	0.0529 (17)	−0.0132 (17)	−0.0312 (16)	0.0138 (14)
O2	0.0692 (18)	0.0578 (17)	0.0560 (16)	−0.0164 (14)	−0.0168 (14)	−0.0007 (13)
O3	0.0769 (18)	0.0463 (15)	0.0472 (15)	−0.0062 (13)	−0.0173 (14)	−0.0067 (12)
P	0.0330 (4)	0.0412 (5)	0.0331 (5)	0.0014 (4)	0.0001 (3)	0.0001 (4)

Geometric parameters (Å, º) top

C1—O1	1.214 (4)	C14—H14A	0.9300
C1—N1	1.365 (4)	C15—C16	1.379 (6)
C1—C2	1.547 (5)	C15—H15A	0.9300
C2—O2	1.223 (4)	C16—H16A	0.9300
C2—C3	1.419 (4)	C17—C18	1.383 (5)
C3—C4	1.448 (5)	C17—C22	1.403 (5)
C3—P	1.746 (3)	C17—P	1.791 (3)
C4—O3	1.210 (4)	C18—C19	1.379 (5)
C4—N1	1.434 (4)	C18—H18A	0.9300
C5—C6	1.367 (5)	C19—C20	1.377 (6)
C5—C10	1.383 (5)	C19—H19A	0.9300
C5—N1	1.447 (4)	C20—C21	1.376 (6)
C6—C7	1.388 (5)	C20—H20A	0.9300
C6—H6A	0.9300	C21—C22	1.372 (5)
C7—C8	1.375 (6)	C21—H21A	0.9300
C7—H7A	0.9300	C22—H22A	0.9300
C8—C9	1.380 (6)	C23—C28	1.377 (5)
C8—H8A	0.9300	C23—C24	1.393 (5)
C9—C10	1.376 (6)	C23—P	1.814 (3)
C9—H9A	0.9300	C24—C25	1.395 (5)
C10—H10A	0.9300	C24—H24A	0.9300
C11—C12	1.371 (5)	C25—C26	1.374 (6)
C11—C16	1.394 (5)	C25—H25A	0.9300
C11—P	1.798 (4)	C26—C27	1.362 (6)
C12—C13	1.387 (6)	C26—H26A	0.9300
C12—H12A	0.9300	C27—C28	1.389 (5)
C13—C14	1.395 (8)	C27—H27A	0.9300
C13—H13A	0.9300	C28—H28A	0.9300
C14—C15	1.344 (8)

O1—C1—N1	127.1 (4)	C11—C16—H16A	120.1
O1—C1—C2	126.1 (3)	C18—C17—C22	119.2 (3)
N1—C1—C2	106.8 (3)	C18—C17—P	121.6 (3)
O2—C2—C3	133.9 (3)	C22—C17—P	119.2 (3)
O2—C2—C1	120.4 (3)	C19—C18—C17	120.3 (4)
C3—C2—C1	105.7 (3)	C19—C18—H18A	119.8
C2—C3—C4	108.8 (3)	C17—C18—H18A	119.8
C2—C3—P	128.3 (3)	C20—C19—C18	119.8 (4)
C4—C3—P	122.5 (2)	C20—C19—H19A	120.1
O3—C4—N1	122.3 (3)	C18—C19—H19A	120.1
O3—C4—C3	130.1 (3)	C21—C20—C19	120.6 (4)
N1—C4—C3	107.6 (3)	C21—C20—H20A	119.7
C6—C5—C10	120.9 (3)	C19—C20—H20A	119.7
C6—C5—N1	120.2 (3)	C22—C21—C20	120.1 (4)
C10—C5—N1	118.9 (3)	C22—C21—H21A	120.0
C5—C6—C7	119.6 (4)	C20—C21—H21A	120.0
C5—C6—H6A	120.2	C21—C22—C17	119.9 (3)
C7—C6—H6A	120.2	C21—C22—H22A	120.0
C8—C7—C6	120.0 (4)	C17—C22—H22A	120.0
C8—C7—H7A	120.0	C28—C23—C24	119.6 (3)
C6—C7—H7A	120.0	C28—C23—P	120.5 (3)
C7—C8—C9	119.9 (4)	C24—C23—P	119.9 (3)
C7—C8—H8A	120.0	C23—C24—C25	119.7 (4)
C9—C8—H8A	120.0	C23—C24—H24A	120.1
C10—C9—C8	120.4 (4)	C25—C24—H24A	120.1
C10—C9—H9A	119.8	C26—C25—C24	120.0 (4)
C8—C9—H9A	119.8	C26—C25—H25A	120.0
C9—C10—C5	119.2 (4)	C24—C25—H25A	120.0
C9—C10—H10A	120.4	C27—C26—C25	120.1 (4)
C5—C10—H10A	120.4	C27—C26—H26A	120.0
C12—C11—C16	119.8 (4)	C25—C26—H26A	120.0
C12—C11—P	122.1 (3)	C26—C27—C28	121.0 (4)
C16—C11—P	118.0 (3)	C26—C27—H27A	119.5
C11—C12—C13	120.0 (5)	C28—C27—H27A	119.5
C11—C12—H12A	120.0	C23—C28—C27	119.7 (4)
C13—C12—H12A	120.0	C23—C28—H28A	120.2
C12—C13—C14	119.1 (5)	C27—C28—H28A	120.2
C12—C13—H13A	120.4	C1—N1—C4	111.1 (3)
C14—C13—H13A	120.4	C1—N1—C5	125.3 (3)
C15—C14—C13	120.9 (5)	C4—N1—C5	123.6 (3)
C15—C14—H14A	119.5	C3—P—C17	111.55 (16)
C13—C14—H14A	119.5	C3—P—C11	108.15 (16)
C14—C15—C16	120.3 (5)	C17—P—C11	108.89 (17)
C14—C15—H15A	119.8	C3—P—C23	113.70 (16)
C16—C15—H15A	119.8	C17—P—C23	107.82 (15)
C15—C16—C11	119.8 (4)	C11—P—C23	106.52 (16)
C15—C16—H16A	120.1

O1—C1—C2—O2	−1.9 (6)	C25—C26—C27—C28	−0.1 (6)
N1—C1—C2—O2	176.3 (3)	C24—C23—C28—C27	0.0 (5)
O1—C1—C2—C3	179.0 (4)	P—C23—C28—C27	178.5 (3)
N1—C1—C2—C3	−2.7 (4)	C26—C27—C28—C23	0.2 (6)
O2—C2—C3—C4	−176.2 (4)	O1—C1—N1—C4	179.9 (4)
C1—C2—C3—C4	2.7 (4)	C2—C1—N1—C4	1.7 (4)
O2—C2—C3—P	−2.9 (6)	O1—C1—N1—C5	1.0 (6)
C1—C2—C3—P	176.0 (3)	C2—C1—N1—C5	−177.3 (3)
C2—C3—C4—O3	177.3 (4)	O3—C4—N1—C1	−179.2 (3)
P—C3—C4—O3	3.5 (5)	C3—C4—N1—C1	−0.1 (4)
C2—C3—C4—N1	−1.7 (4)	O3—C4—N1—C5	−0.2 (5)
P—C3—C4—N1	−175.5 (2)	C3—C4—N1—C5	178.9 (3)
C10—C5—C6—C7	1.1 (6)	C6—C5—N1—C1	123.4 (4)
N1—C5—C6—C7	−176.6 (3)	C10—C5—N1—C1	−54.3 (5)
C5—C6—C7—C8	−0.3 (6)	C6—C5—N1—C4	−55.5 (5)
C6—C7—C8—C9	−0.4 (7)	C10—C5—N1—C4	126.8 (4)
C7—C8—C9—C10	0.3 (7)	C2—C3—P—C17	−119.4 (3)
C8—C9—C10—C5	0.5 (6)	C4—C3—P—C17	53.1 (3)
C6—C5—C10—C9	−1.2 (6)	C2—C3—P—C11	0.4 (4)
N1—C5—C10—C9	176.5 (3)	C4—C3—P—C11	172.9 (3)
C16—C11—C12—C13	0.4 (6)	C2—C3—P—C23	118.4 (3)
P—C11—C12—C13	178.4 (4)	C4—C3—P—C23	−69.1 (3)
C11—C12—C13—C14	−0.9 (8)	C18—C17—P—C3	9.6 (4)
C12—C13—C14—C15	1.3 (9)	C22—C17—P—C3	−172.3 (3)
C13—C14—C15—C16	−1.1 (8)	C18—C17—P—C11	−109.7 (3)
C14—C15—C16—C11	0.5 (7)	C22—C17—P—C11	68.4 (3)
C12—C11—C16—C15	−0.1 (6)	C18—C17—P—C23	135.1 (3)
P—C11—C16—C15	−178.3 (3)	C22—C17—P—C23	−46.8 (3)
C22—C17—C18—C19	1.5 (6)	C12—C11—P—C3	−110.7 (3)
P—C17—C18—C19	179.6 (3)	C16—C11—P—C3	67.4 (3)
C17—C18—C19—C20	−2.7 (7)	C12—C11—P—C17	10.7 (4)
C18—C19—C20—C21	2.2 (8)	C16—C11—P—C17	−171.2 (3)
C19—C20—C21—C22	−0.4 (7)	C12—C11—P—C23	126.7 (3)
C20—C21—C22—C17	−0.9 (7)	C16—C11—P—C23	−55.2 (3)
C18—C17—C22—C21	0.3 (6)	C28—C23—P—C3	29.6 (3)
P—C17—C22—C21	−177.8 (3)	C24—C23—P—C3	−151.9 (3)
C28—C23—C24—C25	−0.3 (5)	C28—C23—P—C17	−94.7 (3)
P—C23—C24—C25	−178.8 (3)	C24—C23—P—C17	83.8 (3)
C23—C24—C25—C26	0.3 (6)	C28—C23—P—C11	148.6 (3)
C24—C25—C26—C27	−0.1 (6)	C24—C23—P—C11	−32.9 (3)

Experimental details

Crystal data
Chemical formula	C₂₈H₂₀NO₃P
M_r	449.42
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	18.171 (4), 12.553 (3), 19.982 (4)
V (Å³)	4557.9 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (XCAD4; Harms & Wocadlo, 1995)
T_min, T_max	0.956, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	3961, 3961, 2590
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.180, 1.07
No. of reflections	3961
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.34

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Acknowledgements

This work was supported by the Shaoxing Key Discipline of Organic Chemistry.

References

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