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

In the title compound, C(26)H(17)OP, the naphthyl ring systems are bent away from each other [dihedral angle = 30.81 (8)°]. In the crystal, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into helical chains along the 2(1) 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 = 376.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.065

S = 1.03

3317 reflections

253 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶); 1455 Friedel pairs

Flack parameter: 0.00 (9)

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811038177/cv5145sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811038177/cv5145Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H17OP	F(000) = 392
Mr = 376.37	Dx = 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

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

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(Fo2) + (0.0113P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3317 reflections	Δρmax = 0.25 e Å−3
253 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983); 1455 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (9)

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	Uiso*/Ueq
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*

	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)

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)

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

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) .