7-Phenyl-7H-dinaphtho­[2,1-b:1′,2′-d]phosphole 7-oxide

Yao, L.; Zhao, C.-Q.

doi:10.1107/S1600536811038177

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2799

https://doi.org/10.1107/S1600536811038177

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7-Phenyl-7H-dinaphtho[2,1-b:1′,2′-d]phosphole 7-oxide

Lan Yao ^a and Chang-Qiu Zhao ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: literabc@hotmail.com

(Received 27 August 2011; accepted 19 September 2011; online 30 September 2011)

In the title compound, C₂₆H₁₇OP, the naphthyl ring systems are bent away from each other [dihedral angle = 30.81 (8)°]. In the crystal, weak intermolecular C—H⋯O interactions link the molecules into helical chains along the 2₁ screw axis.

Related literature

For applications of organophosphorus compounds, see: Antczak & Montchamp (2008 ); Yan & Zhang (2005 ). For related structures, see: Tani et al. (1994 ); Gowda et al. (2010 ).

Experimental

Crystal data

C₂₆H₁₇OP
M_r = 376.37
Monoclinic, P 2₁
a = 10.9637 (12) Å
b = 8.0627 (8) Å
c = 11.0352 (13) Å
β = 94.746 (1)°
V = 972.13 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 298 K
0.26 × 0.17 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.961, T_max = 0.980
4947 measured reflections
3317 independent reflections
2431 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.065
S = 1.03
3317 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ); 1455 Friedel pairs
Flack parameter: 0.00 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯O1ⁱ	0.93	2.47	3.229 (4)	139
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811038177/cv5145sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038177/cv5145Isup3.cml

checkCIF report

Comment top

Organophosphorus compounds are important in various applications (Antczak et al., 2008), including asymmetric catalysis (Yan & Zhang, 2005). In our search for new organophosphorus compounds, we obtained the title compound (I) unintentionally.

The molecule of (I) (Fig. 1) is chiral because of the bent naphthyl rings. All bond lengths and angles are normal and comparable with those observed in the related compounds (Tani et al., 1994; Gowda et al., 2010). Weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into helical chains along screw axis 2₁.

Related literature top

For applications of organophosphorus compounds, see: Antczak & Montchamp (2008); Yan & Zhang (2005). For related structures, see: Tani et al. (1994); Gowda et al. (2010).

Experimental top

n-BuLi(0.2 mmol of a 1.6M hexane solution) was added dropwise to a solution of (R)-2,2'-dibromo-1,l'-binaphthyl (0.1 mmol) in dry ether(5 ml) at -30°C. After stirring for 3 h to form (R)-2,2-Dilithio-l,l'-binaphthalene, it was added to dichlorophenylphosphine(0.1 mmol) at -80°C for 0.5 h, then the mixture was stirred from -80°C to room temperature overnight. After washing with water, the resulting solution was purified by silica gel plate to afford optically pure product 7-phenyl-7H-benzo[e]naphtho[2,1-b]phosphindole. The crystal suitable for X-ray diffraction was obtained from recrystallization with acetone, during this process the product was oxidized to form the title compound.

Structure description top

For applications of organophosphorus compounds, see: Antczak & Montchamp (2008); Yan & Zhang (2005). For related structures, see: Tani et al. (1994); Gowda et al. (2010).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme with 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

7-Phenyl-7H-dinaphtho[2,1-b:1',2'-d]phosphole 7-oxide top

Crystal data top

C₂₆H₁₇OP	F(000) = 392
M_r = 376.37	D_x = 1.286 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1467 reflections
a = 10.9637 (12) Å	θ = 2.5–25.9°
b = 8.0627 (8) Å	µ = 0.16 mm⁻¹
c = 11.0352 (13) Å	T = 298 K
β = 94.746 (1)°	Block, colourless
V = 972.13 (18) Å³	0.26 × 0.17 × 0.13 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3317 independent reflections
Radiation source: fine-focus sealed tube	2431 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→13
T_min = 0.961, T_max = 0.980	k = −9→9
4947 measured reflections	l = −11→13

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0113P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3317 reflections	Δρ_max = 0.25 e Å⁻³
253 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983); 1455 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (9)

Crystal data top

C₂₆H₁₇OP	V = 972.13 (18) Å³
M_r = 376.37	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.9637 (12) Å	µ = 0.16 mm⁻¹
b = 8.0627 (8) Å	T = 298 K
c = 11.0352 (13) Å	0.26 × 0.17 × 0.13 mm
β = 94.746 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3317 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2431 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.980	R_int = 0.027
4947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.065	Δρ_max = 0.25 e Å⁻³
S = 1.03	Δρ_min = −0.21 e Å⁻³
3317 reflections	Absolute structure: Flack (1983); 1455 Friedel pairs
253 parameters	Absolute structure parameter: 0.00 (9)
1 restraint

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
O1	0.90190 (19)	0.5234 (2)	0.13528 (15)	0.0670 (6)
P1	0.81611 (7)	0.41973 (10)	0.20150 (6)	0.0522 (2)
C1	0.6484 (3)	0.4877 (3)	0.3524 (2)	0.0407 (7)
C2	0.6672 (3)	0.4991 (3)	0.2295 (2)	0.0452 (7)
C3	0.5726 (3)	0.5462 (4)	0.1420 (2)	0.0563 (8)
H3	0.5873	0.5517	0.0603	0.068*
C4	0.4601 (3)	0.5835 (3)	0.1773 (3)	0.0599 (8)
H4	0.4009	0.6272	0.1210	0.072*
C5	0.4318 (3)	0.5569 (3)	0.2986 (3)	0.0519 (8)
C6	0.5254 (3)	0.4972 (3)	0.3874 (2)	0.0437 (7)
C7	0.4870 (3)	0.4388 (4)	0.5001 (2)	0.0530 (7)
H7	0.5438	0.3892	0.5561	0.064*
C8	0.3681 (3)	0.4543 (4)	0.5274 (3)	0.0653 (9)
H8	0.3448	0.4142	0.6010	0.078*
C9	0.2806 (3)	0.5308 (4)	0.4447 (3)	0.0709 (10)
H9	0.2018	0.5496	0.4670	0.085*
C10	0.3107 (3)	0.5773 (4)	0.3326 (3)	0.0670 (9)
H10	0.2512	0.6229	0.2775	0.080*
C11	0.7644 (2)	0.4480 (3)	0.4292 (2)	0.0423 (7)
C12	0.8558 (2)	0.3895 (3)	0.3616 (2)	0.0447 (7)
C13	0.9672 (3)	0.3282 (4)	0.4170 (3)	0.0574 (8)
H13	1.0266	0.2876	0.3693	0.069*
C14	0.9880 (3)	0.3285 (4)	0.5413 (3)	0.0590 (9)
H14	1.0580	0.2786	0.5781	0.071*
C15	0.9036 (3)	0.4043 (4)	0.6133 (2)	0.0499 (7)
C16	0.7915 (3)	0.4729 (3)	0.5589 (2)	0.0452 (7)
C17	0.7202 (3)	0.5734 (3)	0.6322 (2)	0.0552 (8)
H17	0.6510	0.6268	0.5968	0.066*
C18	0.7516 (3)	0.5927 (4)	0.7538 (3)	0.0667 (9)
H18	0.7039	0.6589	0.8002	0.080*
C19	0.8567 (3)	0.5122 (4)	0.8097 (3)	0.0711 (10)
H19	0.8749	0.5208	0.8933	0.085*
C20	0.9316 (3)	0.4221 (4)	0.7416 (2)	0.0644 (8)
H20	1.0012	0.3720	0.7790	0.077*
C21	0.7879 (3)	0.2185 (3)	0.1327 (2)	0.0501 (8)
C22	0.6998 (3)	0.1138 (4)	0.1745 (2)	0.0703 (10)
H22	0.6498	0.1511	0.2329	0.084*
C23	0.6864 (3)	−0.0466 (5)	0.1290 (3)	0.0860 (11)
H23	0.6280	−0.1174	0.1572	0.103*
C24	0.7609 (3)	−0.0997 (4)	0.0415 (2)	0.0720 (10)
H24	0.7527	−0.2075	0.0121	0.086*
C25	0.8467 (3)	0.0030 (4)	−0.0029 (2)	0.0640 (9)
H25	0.8951	−0.0340	−0.0627	0.077*
C26	0.8599 (3)	0.1633 (4)	0.0430 (2)	0.0541 (8)
H26	0.9175	0.2341	0.0135	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0700 (14)	0.0669 (14)	0.0672 (13)	−0.0132 (12)	0.0243 (11)	0.0051 (11)
P1	0.0559 (5)	0.0518 (5)	0.0497 (4)	−0.0046 (5)	0.0092 (4)	−0.0004 (4)
C1	0.0473 (19)	0.0344 (15)	0.0398 (16)	−0.0025 (13)	−0.0004 (13)	−0.0029 (12)
C2	0.0487 (19)	0.0425 (17)	0.0440 (16)	−0.0046 (14)	0.0014 (14)	−0.0004 (13)
C3	0.064 (2)	0.0561 (19)	0.0476 (18)	−0.0035 (18)	−0.0030 (17)	0.0003 (15)
C4	0.058 (2)	0.056 (2)	0.062 (2)	0.0044 (18)	−0.0135 (17)	0.0009 (16)
C5	0.049 (2)	0.0460 (18)	0.060 (2)	0.0014 (16)	−0.0009 (17)	−0.0092 (15)
C6	0.0422 (18)	0.0421 (17)	0.0463 (16)	−0.0029 (14)	0.0003 (14)	−0.0081 (13)
C7	0.052 (2)	0.0500 (18)	0.0570 (17)	−0.0023 (18)	0.0072 (14)	−0.0078 (16)
C8	0.065 (2)	0.061 (2)	0.071 (2)	−0.007 (2)	0.0170 (18)	−0.0120 (18)
C9	0.051 (2)	0.071 (2)	0.092 (3)	0.002 (2)	0.014 (2)	−0.026 (2)
C10	0.053 (2)	0.061 (2)	0.085 (2)	0.0067 (18)	−0.0076 (19)	−0.0237 (19)
C11	0.0437 (17)	0.0383 (17)	0.0442 (15)	−0.0042 (14)	−0.0016 (13)	−0.0024 (13)
C12	0.0407 (18)	0.0426 (19)	0.0505 (16)	−0.0013 (15)	0.0026 (14)	−0.0036 (14)
C13	0.047 (2)	0.0593 (19)	0.067 (2)	−0.0005 (17)	0.0077 (17)	−0.0057 (16)
C14	0.044 (2)	0.059 (2)	0.072 (2)	−0.0013 (17)	−0.0088 (18)	0.0041 (17)
C15	0.0506 (19)	0.0494 (18)	0.0488 (17)	−0.0048 (18)	−0.0022 (15)	−0.0006 (16)
C16	0.0475 (19)	0.0418 (18)	0.0452 (16)	−0.0038 (14)	−0.0017 (14)	0.0019 (13)
C17	0.063 (2)	0.054 (2)	0.0480 (18)	0.0026 (17)	0.0000 (16)	−0.0047 (15)
C18	0.085 (3)	0.072 (2)	0.0428 (18)	−0.005 (2)	−0.0008 (17)	−0.0093 (16)
C19	0.083 (3)	0.084 (3)	0.0433 (19)	−0.012 (2)	−0.0124 (18)	−0.0026 (17)
C20	0.063 (2)	0.072 (2)	0.0548 (19)	−0.006 (2)	−0.0160 (16)	0.005 (2)
C21	0.060 (2)	0.050 (2)	0.0409 (17)	0.0031 (16)	0.0077 (15)	0.0005 (13)
C22	0.105 (3)	0.056 (2)	0.0545 (19)	−0.019 (2)	0.0333 (19)	−0.0145 (16)
C23	0.129 (3)	0.067 (3)	0.065 (2)	−0.030 (2)	0.026 (2)	−0.0043 (18)
C24	0.099 (3)	0.058 (2)	0.057 (2)	0.000 (2)	−0.0018 (19)	−0.0132 (18)
C25	0.070 (2)	0.072 (2)	0.0487 (19)	0.019 (2)	−0.0009 (16)	−0.0050 (17)
C26	0.053 (2)	0.061 (2)	0.0479 (18)	0.0046 (17)	0.0022 (15)	0.0022 (16)

Geometric parameters (Å, º) top

O1—P1	1.4937 (18)	C13—C14	1.372 (3)
P1—C12	1.801 (2)	C13—H13	0.9300
P1—C2	1.803 (3)	C14—C15	1.408 (3)
P1—C21	1.807 (3)	C14—H14	0.9300
C1—C2	1.391 (3)	C15—C20	1.431 (3)
C1—C6	1.435 (3)	C15—C16	1.434 (3)
C1—C11	1.503 (3)	C16—C17	1.424 (3)
C2—C3	1.410 (3)	C17—C18	1.366 (3)
C3—C4	1.357 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.418 (4)
C4—C5	1.415 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.366 (4)
C5—C10	1.419 (4)	C19—H19	0.9300
C5—C6	1.443 (3)	C20—H20	0.9300
C6—C7	1.425 (3)	C21—C26	1.389 (3)
C7—C8	1.368 (3)	C21—C22	1.390 (4)
C7—H7	0.9300	C22—C23	1.390 (4)
C8—C9	1.410 (4)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.384 (4)
C9—C10	1.359 (4)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.373 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.381 (3)	C25—C26	1.391 (4)
C11—C16	1.451 (3)	C25—H25	0.9300
C12—C13	1.409 (3)	C26—H26	0.9300

O1—P1—C12	116.43 (12)	C14—C13—C12	119.9 (3)
O1—P1—C2	120.06 (12)	C14—C13—H13	120.0
C12—P1—C2	91.62 (12)	C12—C13—H13	120.0
O1—P1—C21	112.92 (12)	C13—C14—C15	120.2 (3)
C12—P1—C21	108.04 (12)	C13—C14—H14	119.9
C2—P1—C21	105.37 (13)	C15—C14—H14	119.9
C2—C1—C6	118.6 (2)	C14—C15—C20	120.3 (3)
C2—C1—C11	112.1 (3)	C14—C15—C16	120.8 (2)
C6—C1—C11	129.0 (2)	C20—C15—C16	118.8 (3)
C1—C2—C3	121.7 (3)	C17—C16—C15	118.2 (2)
C1—C2—P1	110.7 (2)	C17—C16—C11	124.2 (2)
C3—C2—P1	127.1 (2)	C15—C16—C11	117.3 (2)
C4—C3—C2	119.8 (3)	C18—C17—C16	121.1 (3)
C4—C3—H3	120.1	C18—C17—H17	119.4
C2—C3—H3	120.1	C16—C17—H17	119.4
C3—C4—C5	120.9 (3)	C17—C18—C19	120.3 (3)
C3—C4—H4	119.6	C17—C18—H18	119.8
C5—C4—H4	119.6	C19—C18—H18	119.8
C4—C5—C10	121.1 (3)	C20—C19—C18	120.5 (3)
C4—C5—C6	119.6 (3)	C20—C19—H19	119.8
C10—C5—C6	119.2 (3)	C18—C19—H19	119.8
C7—C6—C1	124.7 (3)	C19—C20—C15	120.6 (3)
C7—C6—C5	117.3 (3)	C19—C20—H20	119.7
C1—C6—C5	117.7 (2)	C15—C20—H20	119.7
C8—C7—C6	121.2 (3)	C26—C21—C22	119.6 (3)
C8—C7—H7	119.4	C26—C21—P1	120.0 (2)
C6—C7—H7	119.4	C22—C21—P1	120.3 (2)
C7—C8—C9	120.5 (3)	C23—C22—C21	120.1 (3)
C7—C8—H8	119.8	C23—C22—H22	120.0
C9—C8—H8	119.8	C21—C22—H22	120.0
C10—C9—C8	120.4 (3)	C22—C23—C24	119.2 (3)
C10—C9—H9	119.8	C22—C23—H23	120.4
C8—C9—H9	119.8	C24—C23—H23	120.4
C9—C10—C5	120.8 (3)	C25—C24—C23	121.6 (3)
C9—C10—H10	119.6	C25—C24—H24	119.2
C5—C10—H10	119.6	C23—C24—H24	119.2
C12—C11—C16	118.8 (2)	C24—C25—C26	118.9 (3)
C12—C11—C1	112.7 (2)	C24—C25—H25	120.5
C16—C11—C1	128.4 (2)	C26—C25—H25	120.5
C11—C12—C13	121.8 (2)	C21—C26—C25	120.6 (3)
C11—C12—P1	110.9 (2)	C21—C26—H26	119.7
C13—C12—P1	127.1 (2)	C25—C26—H26	119.7

C6—C1—C2—C3	10.5 (4)	C2—P1—C12—C11	−4.2 (2)
C11—C1—C2—C3	−175.7 (2)	C21—P1—C12—C11	−110.9 (2)
C6—C1—C2—P1	−161.64 (19)	O1—P1—C12—C13	−54.1 (3)
C11—C1—C2—P1	12.2 (3)	C2—P1—C12—C13	−179.1 (3)
O1—P1—C2—C1	−126.99 (18)	C21—P1—C12—C13	74.2 (3)
C12—P1—C2—C1	−4.9 (2)	C11—C12—C13—C14	−1.2 (4)
C21—P1—C2—C1	104.28 (19)	P1—C12—C13—C14	173.2 (2)
O1—P1—C2—C3	61.4 (3)	C12—C13—C14—C15	−6.1 (4)
C12—P1—C2—C3	−176.5 (2)	C13—C14—C15—C20	−172.7 (3)
C21—P1—C2—C3	−67.3 (3)	C13—C14—C15—C16	3.9 (4)
C1—C2—C3—C4	0.7 (4)	C14—C15—C16—C17	−169.0 (3)
P1—C2—C3—C4	171.5 (2)	C20—C15—C16—C17	7.6 (4)
C2—C3—C4—C5	−7.7 (4)	C14—C15—C16—C11	5.3 (4)
C3—C4—C5—C10	−172.6 (3)	C20—C15—C16—C11	−178.1 (3)
C3—C4—C5—C6	3.1 (4)	C12—C11—C16—C17	161.6 (3)
C2—C1—C6—C7	159.9 (2)	C1—C11—C16—C17	−14.2 (4)
C11—C1—C6—C7	−12.7 (4)	C12—C11—C16—C15	−12.2 (4)
C2—C1—C6—C5	−14.5 (3)	C1—C11—C16—C15	172.0 (3)
C11—C1—C6—C5	172.9 (2)	C15—C16—C17—C18	−5.6 (4)
C4—C5—C6—C7	−166.8 (3)	C11—C16—C17—C18	−179.4 (3)
C10—C5—C6—C7	8.9 (4)	C16—C17—C18—C19	0.0 (4)
C4—C5—C6—C1	8.0 (4)	C17—C18—C19—C20	3.7 (5)
C10—C5—C6—C1	−176.2 (3)	C18—C19—C20—C15	−1.5 (5)
C1—C6—C7—C8	179.1 (3)	C14—C15—C20—C19	172.4 (3)
C5—C6—C7—C8	−6.4 (4)	C16—C15—C20—C19	−4.2 (5)
C6—C7—C8—C9	−0.8 (5)	O1—P1—C21—C26	11.5 (3)
C7—C8—C9—C10	5.7 (5)	C12—P1—C21—C26	−118.7 (2)
C8—C9—C10—C5	−2.9 (5)	C2—P1—C21—C26	144.4 (2)
C4—C5—C10—C9	171.3 (3)	O1—P1—C21—C22	−172.7 (2)
C6—C5—C10—C9	−4.4 (4)	C12—P1—C21—C22	57.1 (3)
C2—C1—C11—C12	−15.8 (3)	C2—P1—C21—C22	−39.8 (3)
C6—C1—C11—C12	157.2 (2)	C26—C21—C22—C23	1.8 (5)
C2—C1—C11—C16	160.2 (2)	P1—C21—C22—C23	−174.0 (3)
C6—C1—C11—C16	−26.8 (4)	C21—C22—C23—C24	−0.5 (5)
C16—C11—C12—C13	10.5 (4)	C22—C23—C24—C25	−1.0 (5)
C1—C11—C12—C13	−173.1 (2)	C23—C24—C25—C26	1.1 (5)
C16—C11—C12—P1	−164.76 (18)	C22—C21—C26—C25	−1.6 (4)
C1—C11—C12—P1	11.7 (3)	P1—C21—C26—C25	174.1 (2)
O1—P1—C12—C11	120.84 (19)	C24—C25—C26—C21	0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O1ⁱ	0.93	2.47	3.229 (4)	139

Symmetry code: (i) −x+2, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₇OP
M_r	376.37
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	10.9637 (12), 8.0627 (8), 11.0352 (13)
β (°)	94.746 (1)
V (Å³)	972.13 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.26 × 0.17 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.961, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	4947, 3317, 2431
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.065, 1.03
No. of reflections	3317
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21
Absolute structure	Flack (1983); 1455 Friedel pairs
Absolute structure parameter	0.00 (9)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O1ⁱ	0.93	2.47	3.229 (4)	138.8

Symmetry code: (i) −x+2, y−1/2, −z.

Acknowledgements

We acknowledge financial support by the Natural Science Foundation of China (grant No. 20772055).

References

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