Tris(4-formyl-phen-yl)phosphane oxide tetra-hydro-furan hemisolvate.

The title compound, C21H15O4P·0.5C4H8O, contains an ordered phosphane oxide in a general position and a tetra-hydro-furan solvent mol-ecule disordered about a twofold axis. All three aldehyde substituents are nearly coplanar with their attached benzene rings, with C-C-C-O torsion angles in the range 1.64 (17)-4.24 (19)°. All three have different conformations with respect to the P=O group, one syn, one anti, and one gauche. Two of the aldehyde substituents form inter-molecular C-H⋯O contacts.

Related literature

For synthetic procedures, see: Bartlett et al. (1978 ▶); Chalier et al. (1996 ▶); Kumagai & Itsuno (2001 ▶). For use as a precursor in supra­molecular chemistry, see: Kakoullis (2007 ▶); Pariya et al. (2008 ▶). For weak hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For related structures, see: Daly (1964 ▶); Etter & Baures (1988 ▶); Siegler et al. (2007 ▶); Spek (1987 ▶); Brock et al. (1985 ▶); Lenstra (2007 ▶); Thierbach et al. (1980 ▶); Baures & Silverton (1990 ▶); Baures (1991 ▶).

Experimental

Crystal data

C21H15O4P·0.5C4H8O

M = 398.35

Monoclinic,

a = 21.371 (3) Å

b = 13.474 (2) Å

c = 13.436 (2) Å

β = 99.018 (9)°

V = 3821.1 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.17 mm−1

T = 110 K

0.45 × 0.43 × 0.38 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.926, T max = 0.937

36155 measured reflections

7598 independent reflections

5928 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.03

7598 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.39 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813020059/fj2638sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020059/fj2638Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020059/fj2638Isup3.cml

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

C21H15O4P·0.5C4H8O	F(000) = 1664
Mr = 398.35	Dx = 1.385 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7492 reflections
a = 21.371 (3) Å	θ = 2.5–33.7°
b = 13.474 (2) Å	µ = 0.17 mm−1
c = 13.436 (2) Å	T = 110 K
β = 99.018 (9)°	Fragment, yellow
V = 3821.1 (10) Å3	0.45 × 0.43 × 0.38 mm
Z = 8

Nonius KappaCCD diffractometer	7598 independent reflections
Radiation source: fine-focus sealed tube	5928 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 33.7°, θmin = 3.0°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −33→33
Tmin = 0.926, Tmax = 0.937	k = −19→21
36155 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0523P)2 + 2.5619P] where P = (Fo2 + 2Fc2)/3
7598 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.39 e Å−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	Occ. (<1)
P1	0.328736 (12)	0.285691 (19)	0.269566 (19)	0.01652 (7)
O1	0.27730 (4)	0.35710 (6)	0.23209 (6)	0.02304 (16)
O2	0.58557 (5)	0.58191 (7)	0.41717 (7)	0.0341 (2)
O3	0.21889 (4)	−0.06198 (6)	0.57196 (7)	0.02736 (18)
O4	0.42853 (5)	−0.02731 (8)	−0.07657 (8)	0.0385 (2)
C1	0.40140 (5)	0.34656 (8)	0.32453 (7)	0.01777 (18)
C2	0.40518 (5)	0.44958 (8)	0.31497 (8)	0.02015 (19)
H2	0.3691	0.4861	0.2848	0.024*
C3	0.46164 (5)	0.49869 (8)	0.34949 (8)	0.0224 (2)
H3	0.4643	0.5687	0.3425	0.027*
C4	0.51435 (5)	0.44465 (8)	0.39446 (8)	0.02102 (19)
C5	0.51021 (5)	0.34239 (9)	0.40684 (8)	0.0227 (2)
H5	0.5459	0.3063	0.4393	0.027*
C6	0.45398 (5)	0.29303 (8)	0.37179 (8)	0.0217 (2)
H6	0.4512	0.2232	0.3798	0.026*
C7	0.57583 (6)	0.49462 (10)	0.42927 (9)	0.0268 (2)
H7	0.6096	0.4556	0.4632	0.032*
C8	0.30889 (5)	0.20142 (7)	0.36429 (7)	0.01710 (17)
C9	0.26866 (5)	0.12078 (8)	0.33428 (8)	0.01918 (19)
H9	0.2543	0.1092	0.2647	0.023*
C10	0.24976 (5)	0.05794 (8)	0.40579 (8)	0.01975 (19)
H10	0.2230	0.0029	0.3855	0.024*
C11	0.27051 (5)	0.07641 (8)	0.50828 (8)	0.01879 (18)
C12	0.30915 (5)	0.15758 (8)	0.53806 (8)	0.0211 (2)
H12	0.3223	0.1703	0.6078	0.025*
C13	0.32874 (5)	0.22025 (8)	0.46671 (8)	0.01944 (18)
H13	0.3554	0.2753	0.4873	0.023*
C14	0.25276 (5)	0.01018 (8)	0.58758 (8)	0.0222 (2)
H14	0.2692	0.0255	0.6557	0.027*
C15	0.35007 (5)	0.21019 (7)	0.16835 (7)	0.01758 (18)
C16	0.39073 (5)	0.12789 (8)	0.18493 (8)	0.0216 (2)
H16	0.4074	0.1081	0.2517	0.026*
C17	0.40635 (6)	0.07555 (9)	0.10328 (9)	0.0244 (2)
H17	0.4348	0.0211	0.1141	0.029*
C18	0.38019 (5)	0.10291 (9)	0.00515 (8)	0.0234 (2)
C19	0.34019 (5)	0.18443 (9)	−0.01138 (8)	0.0236 (2)
H19	0.3228	0.2031	−0.0782	0.028*
C20	0.32550 (5)	0.23890 (8)	0.07013 (8)	0.02047 (19)
H20	0.2988	0.2955	0.0588	0.025*
C21	0.39321 (6)	0.04313 (10)	−0.08199 (9)	0.0303 (3)
H21	0.3722	0.0616	−0.1469	0.036*
O1S	0.45041 (11)	0.23429 (19)	0.84831 (19)	0.0494 (6)	0.50
C1S	0.51269 (14)	0.1940 (3)	0.8648 (3)	0.0386 (6)	0.50
H11S	0.5170	0.1448	0.9202	0.058*	0.50
H12S	0.5443	0.2473	0.8831	0.058*	0.50
C2S	0.5231 (3)	0.1445 (4)	0.7670 (3)	0.0762 (15)	0.50
H21S	0.5678	0.1498	0.7565	0.114*	0.50
H22S	0.5104	0.0738	0.7652	0.114*	0.50
C3S	0.4797 (3)	0.2050 (3)	0.6906 (4)	0.0720 (16)	0.50
H31S	0.5012	0.2656	0.6715	0.108*	0.50
H32S	0.4648	0.1657	0.6292	0.108*	0.50
C4S	0.4278 (2)	0.2296 (4)	0.7434 (3)	0.0701 (14)	0.50
H41S	0.4094	0.2944	0.7196	0.105*	0.50
H42S	0.3943	0.1786	0.7298	0.105*	0.50

	U11	U22	U33	U12	U13	U23
P1	0.01646 (12)	0.01632 (11)	0.01603 (11)	0.00020 (9)	0.00027 (8)	−0.00027 (9)
O1	0.0221 (4)	0.0220 (4)	0.0238 (4)	0.0043 (3)	−0.0003 (3)	0.0014 (3)
O2	0.0340 (5)	0.0338 (5)	0.0348 (5)	−0.0149 (4)	0.0062 (4)	−0.0057 (4)
O3	0.0300 (4)	0.0246 (4)	0.0285 (4)	−0.0029 (3)	0.0075 (3)	0.0020 (3)
O4	0.0330 (5)	0.0477 (6)	0.0363 (5)	−0.0048 (4)	0.0103 (4)	−0.0206 (4)
C1	0.0174 (4)	0.0189 (4)	0.0169 (4)	−0.0015 (3)	0.0024 (3)	−0.0020 (3)
C2	0.0220 (5)	0.0203 (4)	0.0182 (4)	−0.0007 (4)	0.0032 (3)	0.0007 (4)
C3	0.0260 (5)	0.0209 (5)	0.0209 (4)	−0.0049 (4)	0.0050 (4)	−0.0006 (4)
C4	0.0196 (5)	0.0259 (5)	0.0183 (4)	−0.0045 (4)	0.0052 (3)	−0.0043 (4)
C5	0.0176 (5)	0.0259 (5)	0.0244 (5)	0.0008 (4)	0.0021 (4)	−0.0037 (4)
C6	0.0201 (5)	0.0197 (5)	0.0249 (5)	0.0004 (4)	0.0015 (4)	−0.0024 (4)
C7	0.0223 (5)	0.0335 (6)	0.0253 (5)	−0.0075 (4)	0.0059 (4)	−0.0076 (5)
C8	0.0164 (4)	0.0176 (4)	0.0172 (4)	0.0005 (3)	0.0021 (3)	−0.0003 (3)
C9	0.0196 (5)	0.0209 (4)	0.0166 (4)	−0.0014 (4)	0.0014 (3)	−0.0033 (3)
C10	0.0193 (4)	0.0190 (4)	0.0210 (4)	−0.0022 (4)	0.0035 (3)	−0.0027 (4)
C11	0.0202 (4)	0.0177 (4)	0.0190 (4)	0.0018 (3)	0.0049 (3)	−0.0010 (3)
C12	0.0251 (5)	0.0215 (5)	0.0162 (4)	−0.0001 (4)	0.0017 (4)	−0.0019 (3)
C13	0.0208 (5)	0.0186 (4)	0.0182 (4)	−0.0019 (4)	0.0008 (3)	−0.0025 (3)
C14	0.0263 (5)	0.0210 (5)	0.0206 (5)	0.0026 (4)	0.0076 (4)	−0.0006 (4)
C15	0.0177 (4)	0.0187 (4)	0.0159 (4)	−0.0024 (3)	0.0012 (3)	−0.0008 (3)
C16	0.0242 (5)	0.0221 (5)	0.0180 (4)	0.0012 (4)	0.0012 (4)	−0.0007 (4)
C17	0.0242 (5)	0.0250 (5)	0.0239 (5)	0.0005 (4)	0.0037 (4)	−0.0053 (4)
C18	0.0229 (5)	0.0287 (5)	0.0192 (4)	−0.0076 (4)	0.0053 (4)	−0.0064 (4)
C19	0.0231 (5)	0.0311 (5)	0.0160 (4)	−0.0066 (4)	0.0009 (4)	−0.0004 (4)
C20	0.0197 (4)	0.0230 (5)	0.0177 (4)	−0.0028 (4)	−0.0001 (3)	0.0013 (4)
C21	0.0289 (6)	0.0398 (7)	0.0235 (5)	−0.0105 (5)	0.0086 (4)	−0.0111 (5)
O1S	0.0330 (11)	0.0568 (14)	0.0539 (14)	−0.0007 (10)	−0.0072 (10)	0.0064 (11)
C1S	0.0297 (13)	0.0431 (17)	0.0399 (16)	−0.0004 (11)	−0.0043 (12)	−0.0067 (14)
C2S	0.107 (5)	0.078 (3)	0.039 (2)	0.021 (3)	0.001 (2)	−0.008 (2)
C3S	0.128 (5)	0.0307 (17)	0.046 (2)	−0.003 (2)	−0.022 (3)	0.0030 (17)
C4S	0.070 (3)	0.078 (3)	0.050 (2)	−0.030 (2)	−0.0275 (19)	0.036 (2)

P1—O1	1.4880 (8)	C12—H12	0.9500
P1—C8	1.8050 (10)	C13—H13	0.9500
P1—C1	1.8083 (11)	C14—H14	0.9500
P1—C15	1.8129 (10)	C15—C20	1.3963 (14)
O2—C7	1.2099 (16)	C15—C16	1.4050 (15)
O3—C14	1.2107 (14)	C16—C17	1.3882 (15)
O4—C21	1.2078 (17)	C16—H16	0.9500
C1—C2	1.3975 (15)	C17—C18	1.3984 (16)
C1—C6	1.4009 (15)	C17—H17	0.9500
C2—C3	1.3905 (15)	C18—C19	1.3881 (17)
C2—H2	0.9500	C18—C21	1.4830 (16)
C3—C4	1.3968 (16)	C19—C20	1.3944 (15)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.3924 (16)	C20—H20	0.9500
C4—C7	1.4851 (15)	C21—H21	0.9500
C5—C6	1.3895 (15)	O1S—C4S	1.418 (4)
C5—H5	0.9500	O1S—C1S	1.422 (4)
C6—H6	0.9500	C1S—C2S	1.519 (5)
C7—H7	0.9500	C1S—H11S	0.9900
C8—C13	1.3981 (14)	C1S—H12S	0.9900
C8—C9	1.4049 (14)	C2S—C3S	1.510 (6)
C9—C10	1.3873 (15)	C2S—H21S	0.9900
C9—H9	0.9500	C2S—H22S	0.9900
C10—C11	1.4013 (14)	C3S—C4S	1.446 (8)
C10—H10	0.9500	C3S—H31S	0.9900
C11—C12	1.3909 (15)	C3S—H32S	0.9900
C11—C14	1.4839 (15)	C4S—H41S	0.9900
C12—C13	1.3904 (15)	C4S—H42S	0.9900
O1—P1—C8	113.74 (5)	C11—C14—H14	117.6
O1—P1—C1	112.73 (5)	C20—C15—C16	120.01 (10)
C8—P1—C1	106.20 (5)	C20—C15—P1	116.88 (8)
O1—P1—C15	111.61 (5)	C16—C15—P1	123.09 (8)
C8—P1—C15	106.89 (5)	C17—C16—C15	119.67 (10)
C1—P1—C15	105.07 (5)	C17—C16—H16	120.2
C2—C1—C6	119.95 (10)	C15—C16—H16	120.2
C2—C1—P1	118.12 (8)	C16—C17—C18	120.06 (11)
C6—C1—P1	121.87 (8)	C16—C17—H17	120.0
C3—C2—C1	120.11 (10)	C18—C17—H17	120.0
C3—C2—H2	119.9	C19—C18—C17	120.31 (10)
C1—C2—H2	119.9	C19—C18—C21	119.37 (11)
C2—C3—C4	119.68 (10)	C17—C18—C21	120.29 (11)
C2—C3—H3	120.2	C18—C19—C20	119.97 (10)
C4—C3—H3	120.2	C18—C19—H19	120.0
C5—C4—C3	120.36 (10)	C20—C19—H19	120.0
C5—C4—C7	118.73 (11)	C19—C20—C15	119.93 (10)
C3—C4—C7	120.91 (10)	C19—C20—H20	120.0
C6—C5—C4	120.07 (10)	C15—C20—H20	120.0
C6—C5—H5	120.0	O4—C21—C18	124.90 (12)
C4—C5—H5	120.0	O4—C21—H21	117.6
C5—C6—C1	119.79 (10)	C18—C21—H21	117.6
C5—C6—H6	120.1	C4S—O1S—C1S	107.6 (3)
C1—C6—H6	120.1	O1S—C1S—C2S	107.0 (3)
O2—C7—C4	124.11 (12)	O1S—C1S—H11S	110.3
O2—C7—H7	117.9	C2S—C1S—H11S	110.3
C4—C7—H7	117.9	O1S—C1S—H12S	110.3
C13—C8—C9	120.03 (9)	C2S—C1S—H12S	110.3
C13—C8—P1	120.75 (8)	H11S—C1S—H12S	108.6
C9—C8—P1	119.01 (7)	C3S—C2S—C1S	101.2 (4)
C10—C9—C8	120.31 (9)	C3S—C2S—H21S	111.5
C10—C9—H9	119.8	C1S—C2S—H21S	111.5
C8—C9—H9	119.8	C3S—C2S—H22S	111.5
C9—C10—C11	119.38 (10)	C1S—C2S—H22S	111.5
C9—C10—H10	120.3	H21S—C2S—H22S	109.4
C11—C10—H10	120.3	C4S—C3S—C2S	103.1 (4)
C12—C11—C10	120.30 (10)	C4S—C3S—H31S	111.2
C12—C11—C14	118.26 (9)	C2S—C3S—H31S	111.2
C10—C11—C14	121.44 (10)	C4S—C3S—H32S	111.2
C13—C12—C11	120.57 (9)	C2S—C3S—H32S	111.2
C13—C12—H12	119.7	H31S—C3S—H32S	109.1
C11—C12—H12	119.7	O1S—C4S—C3S	109.3 (3)
C12—C13—C8	119.39 (10)	O1S—C4S—H41S	109.8
C12—C13—H13	120.3	C3S—C4S—H41S	109.8
C8—C13—H13	120.3	O1S—C4S—H42S	109.8
O3—C14—C11	124.87 (10)	C3S—C4S—H42S	109.8
O3—C14—H14	117.6	H41S—C4S—H42S	108.3
O1—P1—C1—C2	−8.16 (10)	C14—C11—C12—C13	178.05 (10)
C8—P1—C1—C2	−133.35 (8)	C11—C12—C13—C8	0.44 (16)
C15—P1—C1—C2	113.60 (9)	C9—C8—C13—C12	1.05 (16)
O1—P1—C1—C6	174.63 (8)	P1—C8—C13—C12	175.71 (8)
C8—P1—C1—C6	49.43 (10)	C12—C11—C14—O3	179.01 (11)
C15—P1—C1—C6	−63.62 (10)	C10—C11—C14—O3	−1.64 (17)
C6—C1—C2—C3	1.99 (16)	O1—P1—C15—C20	11.07 (10)
P1—C1—C2—C3	−175.28 (8)	C8—P1—C15—C20	136.02 (8)
C1—C2—C3—C4	−0.51 (15)	C1—P1—C15—C20	−111.41 (9)
C2—C3—C4—C5	−1.42 (16)	O1—P1—C15—C16	−170.73 (9)
C2—C3—C4—C7	178.15 (10)	C8—P1—C15—C16	−45.78 (10)
C3—C4—C5—C6	1.87 (16)	C1—P1—C15—C16	66.79 (10)
C7—C4—C5—C6	−177.70 (10)	C20—C15—C16—C17	0.10 (16)
C4—C5—C6—C1	−0.39 (16)	P1—C15—C16—C17	−178.04 (8)
C2—C1—C6—C5	−1.54 (16)	C15—C16—C17—C18	−1.91 (17)
P1—C1—C6—C5	175.63 (8)	C16—C17—C18—C19	2.16 (17)
C5—C4—C7—O2	175.74 (11)	C16—C17—C18—C21	−175.80 (11)
C3—C4—C7—O2	−3.83 (17)	C17—C18—C19—C20	−0.57 (17)
O1—P1—C8—C13	−97.60 (9)	C21—C18—C19—C20	177.40 (10)
C1—P1—C8—C13	26.97 (10)	C18—C19—C20—C15	−1.24 (16)
C15—P1—C8—C13	138.76 (9)	C16—C15—C20—C19	1.48 (16)
O1—P1—C8—C9	77.11 (9)	P1—C15—C20—C19	179.73 (8)
C1—P1—C8—C9	−158.32 (8)	C19—C18—C21—O4	177.78 (12)
C15—P1—C8—C9	−46.53 (9)	C17—C18—C21—O4	−4.24 (19)
C13—C8—C9—C10	−1.68 (16)	C4S—O1S—C1S—C2S	−11.3 (4)
P1—C8—C9—C10	−176.43 (8)	O1S—C1S—C2S—C3S	28.0 (4)
C8—C9—C10—C11	0.82 (16)	C1S—C2S—C3S—C4S	−33.6 (5)
C9—C10—C11—C12	0.67 (16)	C1S—O1S—C4S—C3S	−11.4 (4)
C9—C10—C11—C14	−178.66 (10)	C2S—C3S—C4S—O1S	29.0 (5)
C10—C11—C12—C13	−1.31 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3i	0.95	2.56	3.4303 (16)	152
C14—H14···O1ii	0.95	2.50	3.1575 (14)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3i	0.95	2.56	3.4303 (16)	152
C14—H14⋯O1ii	0.95	2.50	3.1575 (14)	127

Symmetry codes: (i) ; (ii) .