3-[2-(Triphenyl-phosphanyl-idene)acet-yl]-2H-chromen-2-one.

In the title compound, C(29)H(21)O(3)P, a coumarin-substitued ylid, the P atom is linked to three benzene rings and a planar coumarin moiety via a methyl-enecarbonyl group. The bond lengths in the P=C-C=O fragment clearly indicate a delocalized system involving the olefinic and carbonyl bonds. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O inter-action that results in an S7 graph-set ring motif. In the crystal, mol-ecules are linked into a three-dimensional framework by C-H⋯O hydrogen bonds.

Related literature

For applications and biological activity of coumarin, see: Kabak et al. (1999 ▶); El-Ansary et al. (1992 ▶); Czerpack & Skolska (1982 ▶); Reddy & Somayojulu (1981 ▶); pan class="Gene">Jund et al. (1971 ▶). For the crystal structure of a related compound, see: Schobert et al. (2000 ▶).

Experimental

Crystal data

C29H21O3P

M = 448.43

Triclinic,

a = 9.7837 (12) Å

b = 10.3917 (14) Å

c = 12.2925 (17) Å

α = 108.669 (4)°

β = 104.484 (4)°

γ = 99.746 (4)°

V = 1103.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.46 × 0.41 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.932, T max = 0.949

36693 measured reflections

4102 independent reflections

3716 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.07

4102 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300127X/pv2616sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300127X/pv2616Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300127X/pv2616Isup3.cml

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

C29H21O3P	Z = 2
Mr = 448.43	F(000) = 468
Triclinic, P1	Dx = 1.350 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7837 (12) Å	Cell parameters from 7459 reflections
b = 10.3917 (14) Å	θ = 3.2–26.4°
c = 12.2925 (17) Å	µ = 0.16 mm−1
α = 108.669 (4)°	T = 100 K
β = 104.484 (4)°	Block, yellow
γ = 99.746 (4)°	0.46 × 0.41 × 0.34 mm
V = 1103.2 (3) Å3

Bruker APEXII CCD diffractometer	4102 independent reflections
Radiation source: fine-focus sealed tube	3716 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scan	θmax = 25.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.932, Tmax = 0.949	k = −12→12
36693 measured reflections	l = −14→14

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.6733P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4102 reflections	Δρmax = 0.32 e Å−3
299 parameters	Δρmin = −0.40 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.041 (3)

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
P1	0.22033 (4)	0.28713 (4)	0.37638 (3)	0.01546 (12)
O1	0.54288 (11)	0.37113 (10)	0.89176 (9)	0.0192 (2)
O2	0.32695 (11)	0.37143 (11)	0.78335 (9)	0.0227 (2)
O3	0.32489 (11)	0.06590 (10)	0.47387 (9)	0.0213 (2)
C1	0.67160 (16)	0.33179 (15)	0.90304 (13)	0.0178 (3)
C2	0.78228 (17)	0.39917 (16)	1.01425 (13)	0.0222 (3)
H2A	0.7684	0.4680	1.0801	0.027*
C3	0.91346 (17)	0.36328 (17)	1.02647 (14)	0.0251 (3)
H3A	0.9915	0.4093	1.1014	0.030*
C4	0.93292 (18)	0.26033 (17)	0.93023 (14)	0.0264 (3)
H4A	1.0236	0.2366	0.9403	0.032*
C5	0.82116 (17)	0.19312 (16)	0.82082 (14)	0.0235 (3)
H5A	0.8346	0.1223	0.7560	0.028*
C6	0.68754 (16)	0.22893 (15)	0.80479 (13)	0.0187 (3)
C7	0.57153 (16)	0.17586 (15)	0.69048 (12)	0.0183 (3)
H7A	0.5774	0.1018	0.6237	0.022*
C8	0.45432 (15)	0.22872 (14)	0.67566 (12)	0.0166 (3)
C9	0.43323 (15)	0.32761 (14)	0.78122 (12)	0.0171 (3)
C10	0.35227 (15)	0.19030 (15)	0.54841 (12)	0.0168 (3)
C11	0.30703 (15)	0.30007 (15)	0.52151 (12)	0.0174 (3)
H11A	0.3250	0.3869	0.5869	0.021*
C12	0.05596 (15)	0.14349 (15)	0.29385 (13)	0.0179 (3)
C13	−0.01368 (16)	0.10991 (16)	0.17037 (13)	0.0221 (3)
H13A	0.0293	0.1585	0.1284	0.027*
C14	−0.14561 (17)	0.00551 (17)	0.10911 (13)	0.0244 (3)
H14A	−0.1942	−0.0159	0.0256	0.029*
C15	−0.20609 (17)	−0.06731 (17)	0.16996 (14)	0.0275 (4)
H15A	−0.2963	−0.1388	0.1281	0.033*
C16	−0.13548 (18)	−0.03636 (18)	0.29201 (15)	0.0303 (4)
H16A	−0.1765	−0.0880	0.3329	0.036*
C17	−0.00522 (16)	0.06981 (17)	0.35421 (13)	0.0233 (3)
H17A	0.0421	0.0921	0.4381	0.028*
C18	0.17083 (17)	0.44966 (15)	0.39085 (13)	0.0198 (3)
C19	0.28216 (19)	0.57658 (16)	0.45100 (15)	0.0274 (3)
H19A	0.3809	0.5754	0.4821	0.033*
C20	0.2484 (2)	0.70386 (18)	0.46519 (16)	0.0346 (4)
H20A	0.3235	0.7902	0.5075	0.042*
C21	0.1052 (2)	0.70496 (19)	0.41764 (16)	0.0370 (4)
H21A	0.0830	0.7922	0.4245	0.044*
C22	−0.0057 (2)	0.5810 (2)	0.36029 (15)	0.0357 (4)
H22A	−0.1041	0.5833	0.3295	0.043*
C23	0.02628 (18)	0.45223 (18)	0.34736 (14)	0.0260 (3)
H23A	−0.0503	0.3668	0.3090	0.031*
C24	0.33364 (15)	0.26597 (15)	0.27860 (12)	0.0181 (3)
C25	0.41259 (18)	0.16625 (18)	0.27691 (15)	0.0278 (4)
H25A	0.4064	0.1125	0.3260	0.033*
C26	0.5006 (2)	0.1454 (2)	0.20336 (17)	0.0350 (4)
H26A	0.5549	0.0777	0.2028	0.042*
C27	0.50937 (18)	0.22260 (18)	0.13103 (15)	0.0303 (4)
H27A	0.5701	0.2083	0.0813	0.036*
C28	0.42996 (19)	0.32023 (16)	0.13125 (14)	0.0287 (4)
H28A	0.4352	0.3724	0.0808	0.034*
C29	0.34227 (17)	0.34276 (16)	0.20488 (13)	0.0238 (3)
H29A	0.2882	0.4105	0.2050	0.029*

	U11	U22	U33	U12	U13	U23
P1	0.0158 (2)	0.01588 (19)	0.01475 (19)	0.00488 (14)	0.00474 (14)	0.00582 (14)
O1	0.0200 (5)	0.0226 (5)	0.0143 (5)	0.0084 (4)	0.0057 (4)	0.0046 (4)
O2	0.0203 (5)	0.0268 (6)	0.0200 (5)	0.0101 (4)	0.0074 (4)	0.0050 (4)
O3	0.0249 (5)	0.0174 (5)	0.0173 (5)	0.0062 (4)	0.0046 (4)	0.0023 (4)
C1	0.0199 (7)	0.0190 (7)	0.0177 (7)	0.0069 (6)	0.0072 (6)	0.0094 (6)
C2	0.0261 (8)	0.0239 (7)	0.0157 (7)	0.0079 (6)	0.0065 (6)	0.0063 (6)
C3	0.0247 (8)	0.0312 (8)	0.0177 (7)	0.0083 (7)	0.0023 (6)	0.0103 (6)
C4	0.0246 (8)	0.0338 (9)	0.0258 (8)	0.0154 (7)	0.0077 (6)	0.0144 (7)
C5	0.0282 (8)	0.0258 (8)	0.0200 (7)	0.0142 (6)	0.0090 (6)	0.0088 (6)
C6	0.0235 (7)	0.0180 (7)	0.0173 (7)	0.0075 (6)	0.0075 (6)	0.0085 (6)
C7	0.0242 (7)	0.0159 (7)	0.0152 (7)	0.0067 (6)	0.0076 (6)	0.0050 (5)
C8	0.0197 (7)	0.0143 (6)	0.0157 (7)	0.0032 (5)	0.0069 (6)	0.0054 (5)
C9	0.0180 (7)	0.0170 (7)	0.0157 (7)	0.0033 (5)	0.0056 (5)	0.0060 (5)
C10	0.0158 (7)	0.0181 (7)	0.0156 (7)	0.0033 (5)	0.0066 (5)	0.0046 (5)
C11	0.0181 (7)	0.0176 (7)	0.0132 (6)	0.0040 (5)	0.0031 (5)	0.0035 (5)
C12	0.0161 (7)	0.0177 (7)	0.0186 (7)	0.0052 (5)	0.0054 (5)	0.0053 (6)
C13	0.0231 (8)	0.0242 (7)	0.0185 (7)	0.0047 (6)	0.0060 (6)	0.0086 (6)
C14	0.0225 (8)	0.0280 (8)	0.0173 (7)	0.0048 (6)	0.0028 (6)	0.0053 (6)
C15	0.0190 (7)	0.0298 (8)	0.0249 (8)	−0.0010 (6)	0.0044 (6)	0.0050 (7)
C16	0.0247 (8)	0.0379 (9)	0.0256 (8)	−0.0019 (7)	0.0096 (7)	0.0131 (7)
C17	0.0205 (7)	0.0297 (8)	0.0178 (7)	0.0032 (6)	0.0061 (6)	0.0085 (6)
C18	0.0259 (8)	0.0220 (7)	0.0168 (7)	0.0108 (6)	0.0100 (6)	0.0097 (6)
C19	0.0321 (9)	0.0225 (8)	0.0309 (8)	0.0085 (7)	0.0146 (7)	0.0105 (7)
C20	0.0533 (11)	0.0227 (8)	0.0363 (9)	0.0135 (8)	0.0247 (9)	0.0128 (7)
C21	0.0681 (13)	0.0321 (9)	0.0290 (9)	0.0317 (9)	0.0267 (9)	0.0174 (8)
C22	0.0452 (10)	0.0527 (11)	0.0235 (8)	0.0361 (9)	0.0151 (8)	0.0183 (8)
C23	0.0284 (8)	0.0332 (9)	0.0182 (7)	0.0155 (7)	0.0069 (6)	0.0089 (6)
C24	0.0163 (7)	0.0184 (7)	0.0158 (7)	0.0014 (5)	0.0040 (5)	0.0041 (5)
C25	0.0320 (9)	0.0336 (9)	0.0297 (8)	0.0166 (7)	0.0170 (7)	0.0182 (7)
C26	0.0362 (10)	0.0445 (10)	0.0385 (10)	0.0236 (8)	0.0228 (8)	0.0197 (8)
C27	0.0292 (9)	0.0338 (9)	0.0253 (8)	0.0026 (7)	0.0161 (7)	0.0055 (7)
C28	0.0396 (9)	0.0213 (8)	0.0221 (8)	−0.0013 (7)	0.0142 (7)	0.0057 (6)
C29	0.0306 (8)	0.0188 (7)	0.0211 (7)	0.0048 (6)	0.0091 (6)	0.0067 (6)

P1—C11	1.7237 (14)	C14—C15	1.384 (2)
P1—C12	1.8014 (15)	C14—H14A	0.9500
P1—C18	1.8019 (15)	C15—C16	1.389 (2)
P1—C24	1.8171 (15)	C15—H15A	0.9500
O1—C1	1.3769 (17)	C16—C17	1.387 (2)
O1—C9	1.3838 (17)	C16—H16A	0.9500
O2—C9	1.2064 (18)	C17—H17A	0.9500
O3—C10	1.2586 (17)	C18—C23	1.389 (2)
C1—C2	1.386 (2)	C18—C19	1.400 (2)
C1—C6	1.396 (2)	C19—C20	1.385 (2)
C2—C3	1.382 (2)	C19—H19A	0.9500
C2—H2A	0.9500	C20—C21	1.380 (3)
C3—C4	1.397 (2)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.377 (3)
C4—C5	1.377 (2)	C21—H21A	0.9500
C4—H4A	0.9500	C22—C23	1.395 (2)
C5—C6	1.403 (2)	C22—H22A	0.9500
C5—H5A	0.9500	C23—H23A	0.9500
C6—C7	1.436 (2)	C24—C25	1.391 (2)
C7—C8	1.350 (2)	C24—C29	1.394 (2)
C7—H7A	0.9500	C25—C26	1.390 (2)
C8—C9	1.4610 (19)	C25—H25A	0.9500
C8—C10	1.5123 (19)	C26—C27	1.383 (3)
C10—C11	1.395 (2)	C26—H26A	0.9500
C11—H11A	0.9500	C27—C28	1.378 (3)
C12—C17	1.388 (2)	C27—H27A	0.9500
C12—C13	1.398 (2)	C28—C29	1.390 (2)
C13—C14	1.388 (2)	C28—H28A	0.9500
C13—H13A	0.9500	C29—H29A	0.9500
C11—P1—C12	114.64 (7)	C15—C14—H14A	120.1
C11—P1—C18	106.69 (7)	C13—C14—H14A	120.1
C12—P1—C18	108.00 (7)	C14—C15—C16	120.32 (14)
C11—P1—C24	114.32 (7)	C14—C15—H15A	119.8
C12—P1—C24	105.28 (6)	C16—C15—H15A	119.8
C18—P1—C24	107.59 (7)	C17—C16—C15	120.08 (15)
C1—O1—C9	122.54 (11)	C17—C16—H16A	120.0
O1—C1—C2	117.19 (13)	C15—C16—H16A	120.0
O1—C1—C6	120.27 (13)	C16—C17—C12	119.93 (14)
C2—C1—C6	122.53 (13)	C16—C17—H17A	120.0
C3—C2—C1	118.02 (14)	C12—C17—H17A	120.0
C3—C2—H2A	121.0	C23—C18—C19	119.69 (14)
C1—C2—H2A	121.0	C23—C18—P1	122.02 (12)
C2—C3—C4	120.94 (14)	C19—C18—P1	118.27 (12)
C2—C3—H3A	119.5	C20—C19—C18	120.03 (16)
C4—C3—H3A	119.5	C20—C19—H19A	120.0
C5—C4—C3	120.28 (14)	C18—C19—H19A	120.0
C5—C4—H4A	119.9	C21—C20—C19	119.81 (17)
C3—C4—H4A	119.9	C21—C20—H20A	120.1
C4—C5—C6	120.17 (14)	C19—C20—H20A	120.1
C4—C5—H5A	119.9	C22—C21—C20	120.71 (15)
C6—C5—H5A	119.9	C22—C21—H21A	119.6
C1—C6—C5	118.03 (13)	C20—C21—H21A	119.6
C1—C6—C7	117.86 (13)	C21—C22—C23	120.09 (16)
C5—C6—C7	123.85 (13)	C21—C22—H22A	120.0
C8—C7—C6	121.52 (13)	C23—C22—H22A	120.0
C8—C7—H7A	119.2	C18—C23—C22	119.60 (16)
C6—C7—H7A	119.2	C18—C23—H23A	120.2
C7—C8—C9	119.72 (13)	C22—C23—H23A	120.2
C7—C8—C10	118.80 (12)	C25—C24—C29	119.40 (14)
C9—C8—C10	121.38 (12)	C25—C24—P1	117.57 (11)
O2—C9—O1	116.03 (12)	C29—C24—P1	123.02 (11)
O2—C9—C8	126.74 (13)	C26—C25—C24	119.95 (15)
O1—C9—C8	117.16 (12)	C26—C25—H25A	120.0
O3—C10—C11	125.68 (13)	C24—C25—H25A	120.0
O3—C10—C8	117.62 (12)	C27—C26—C25	120.35 (16)
C11—C10—C8	116.45 (12)	C27—C26—H26A	119.8
C10—C11—P1	123.73 (11)	C25—C26—H26A	119.8
C10—C11—H11A	118.1	C28—C27—C26	119.91 (15)
P1—C11—H11A	118.1	C28—C27—H27A	120.0
C17—C12—C13	119.83 (13)	C26—C27—H27A	120.0
C17—C12—P1	119.88 (11)	C27—C28—C29	120.33 (15)
C13—C12—P1	120.23 (11)	C27—C28—H28A	119.8
C14—C13—C12	120.01 (14)	C29—C28—H28A	119.8
C14—C13—H13A	120.0	C28—C29—C24	120.05 (15)
C12—C13—H13A	120.0	C28—C29—H29A	120.0
C15—C14—C13	119.81 (14)	C24—C29—H29A	120.0
C9—O1—C1—C2	170.11 (13)	C24—P1—C12—C13	−44.96 (13)
C9—O1—C1—C6	−9.35 (19)	C17—C12—C13—C14	1.6 (2)
O1—C1—C2—C3	−178.61 (13)	P1—C12—C13—C14	−175.62 (12)
C6—C1—C2—C3	0.8 (2)	C12—C13—C14—C15	−1.5 (2)
C1—C2—C3—C4	−1.1 (2)	C13—C14—C15—C16	0.0 (2)
C2—C3—C4—C5	0.3 (2)	C14—C15—C16—C17	1.3 (3)
C3—C4—C5—C6	0.8 (2)	C15—C16—C17—C12	−1.2 (3)
O1—C1—C6—C5	179.69 (12)	C13—C12—C17—C16	−0.3 (2)
C2—C1—C6—C5	0.3 (2)	P1—C12—C17—C16	176.96 (12)
O1—C1—C6—C7	5.4 (2)	C11—P1—C18—C23	−121.10 (13)
C2—C1—C6—C7	−174.07 (13)	C12—P1—C18—C23	2.62 (14)
C4—C5—C6—C1	−1.1 (2)	C24—P1—C18—C23	115.81 (13)
C4—C5—C6—C7	172.88 (14)	C11—P1—C18—C19	57.07 (13)
C1—C6—C7—C8	3.8 (2)	C12—P1—C18—C19	−179.21 (11)
C5—C6—C7—C8	−170.22 (14)	C24—P1—C18—C19	−66.02 (13)
C6—C7—C8—C9	−8.9 (2)	C23—C18—C19—C20	−1.1 (2)
C6—C7—C8—C10	167.60 (13)	P1—C18—C19—C20	−179.28 (12)
C1—O1—C9—O2	−178.77 (12)	C18—C19—C20—C21	−1.4 (2)
C1—O1—C9—C8	4.13 (18)	C19—C20—C21—C22	2.6 (3)
C7—C8—C9—O2	−171.75 (14)	C20—C21—C22—C23	−1.4 (2)
C10—C8—C9—O2	11.9 (2)	C19—C18—C23—C22	2.3 (2)
C7—C8—C9—O1	5.00 (19)	P1—C18—C23—C22	−179.58 (11)
C10—C8—C9—O1	−171.38 (12)	C21—C22—C23—C18	−1.1 (2)
C7—C8—C10—O3	38.62 (19)	C11—P1—C24—C25	47.08 (14)
C9—C8—C10—O3	−144.96 (13)	C12—P1—C24—C25	−79.63 (13)
C7—C8—C10—C11	−135.98 (14)	C18—P1—C24—C25	165.36 (12)
C9—C8—C10—C11	40.43 (18)	C11—P1—C24—C29	−134.07 (12)
O3—C10—C11—P1	−6.8 (2)	C12—P1—C24—C29	99.21 (13)
C8—C10—C11—P1	167.32 (10)	C18—P1—C24—C29	−15.79 (14)
C12—P1—C11—C10	55.66 (14)	C29—C24—C25—C26	0.9 (2)
C18—P1—C11—C10	175.16 (12)	P1—C24—C25—C26	179.75 (13)
C24—P1—C11—C10	−66.05 (14)	C24—C25—C26—C27	−0.4 (3)
C11—P1—C12—C17	11.30 (15)	C25—C26—C27—C28	−0.4 (3)
C18—P1—C12—C17	−107.47 (12)	C26—C27—C28—C29	0.8 (3)
C24—P1—C12—C17	137.81 (12)	C27—C28—C29—C24	−0.3 (2)
C11—P1—C12—C13	−171.47 (11)	C25—C24—C29—C28	−0.5 (2)
C18—P1—C12—C13	69.77 (13)	P1—C24—C29—C28	−179.31 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.95	2.45	3.378 (2)	166
C7—H7A···O3ii	0.95	2.28	3.171 (2)	156
C22—H22A···O2iii	0.95	2.48	3.398 (2)	163
C25—H25A···O3	0.95	2.31	3.168 (2)	150
C28—H28A···O1iv	0.95	2.54	3.281 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.95	2.45	3.378 (2)	166
C7—H7A⋯O3ii	0.95	2.28	3.171 (2)	156
C22—H22A⋯O2iii	0.95	2.48	3.398 (2)	163
C25—H25A⋯O3	0.95	2.31	3.168 (2)	150
C28—H28A⋯O1iv	0.95	2.54	3.281 (2)	135

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