A second monoclinic modification of triphenyl­phosphine oxide hemihydrate

Ng, S.W.

doi:10.1107/S1600536809019254

organic compounds

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Volume 65| Part 6| June 2009| Page o1431

doi:10.1107/S1600536809019254

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A second monoclinic modification of triphenylphosphine oxide hemihydrate

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 May 2009; accepted 21 May 2009; online 29 May 2009)

In the crystal of the title compound, C₁₈H₁₅OP·0.5H₂O, a water molecule links to two adjacent triphenylphosphine molecules by way of O—H⋯O hydrogen bonds. The crystal is twinned, the minor twin component being 36%.

Related literature

For the C2/c modification, see: Baures (1991 ). For the Fdd2 modification, see: Baures & Silverton (1990 ) (the authors mention a Cc modification without providing details).

Experimental

Crystal data

C₁₈H₁₅OP·0.5H₂O
M_r = 287.28
Monoclinic, C c
a = 9.4313 (1) Å
b = 32.1930 (4) Å
c = 10.8435 (1) Å
β = 115.742 (1)°
V = 2965.59 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.947, T_max = 0.965
14206 measured reflections
6609 independent reflections
6504 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.065
S = 1.02
6609 reflections
379 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 3203 Friedel pairs
Flack parameter: 0.02 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O1	0.84 (3)	2.05 (2)	2.836 (2)	156 (4)
O1W—H2⋯O2	0.83 (3)	2.09 (2)	2.870 (2)	158 (3)

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019254/xu2526sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019254/xu2526Isup2.hkl

checkCIF report

Related literature top

For the C2/c modification, see: Baures (1991). For the Fdd2 modification, see: Baures & Silverton (1990) (the authors mention a Cc modification without providing details).

Experimental top

The compound was the unexpected crystalline product of the reaction between tetracyclohexyltin (1 g, 2.2 mmol) and dibromotriphenylphosphine (1 g, 2.4 mmol) in ethanol. The reactants were heated in the solvent for an hour. The solvent was allowed to evaporate to leave behind a mixture of crystalline products. The product probably resulted from the hydrolysis of the phosphine.

Computing details top

Data collection: APEX2 (Bruker, 2008) [Au SMART software for SMART machine?]; cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 70% probability level, and hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.

triphenylphosphine oxide hemihydrate top

Crystal data top

C₁₈H₁₅OP·0.5H₂O	F(000) = 1208
M_r = 287.28	D_x = 1.287 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9366 reflections
a = 9.4313 (1) Å	θ = 2.4–28.2°
b = 32.1930 (4) Å	µ = 0.18 mm⁻¹
c = 10.8435 (1) Å	T = 100 K
β = 115.742 (1)°	Block, colorless
V = 2965.59 (6) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	6609 independent reflections
Radiation source: fine-focus sealed tube	6504 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.947, T_max = 0.965	k = −41→41
14206 measured reflections	l = −14→14

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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0453P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
6609 reflections	Δρ_max = 0.24 e Å⁻³
379 parameters	Δρ_min = −0.17 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 3203 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

Crystal data top

C₁₈H₁₅OP·0.5H₂O	V = 2965.59 (6) Å³
M_r = 287.28	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 9.4313 (1) Å	µ = 0.18 mm⁻¹
b = 32.1930 (4) Å	T = 100 K
c = 10.8435 (1) Å	0.30 × 0.25 × 0.20 mm
β = 115.742 (1)°

Data collection top

Bruker SMART APEX diffractometer	6609 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6504 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.965	R_int = 0.019
14206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.065	Δρ_max = 0.24 e Å⁻³
S = 1.02	Δρ_min = −0.17 e Å⁻³
6609 reflections	Absolute structure: Flack (1983), 3203 Friedel pairs
379 parameters	Absolute structure parameter: 0.02 (5)
4 restraints

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

	x	y	z	U_iso*/U_eq
P1	0.50187 (5)	0.437805 (13)	0.50006 (5)	0.01863 (12)
P2	0.27142 (5)	0.309772 (14)	−0.01509 (4)	0.01939 (12)
O1	0.39737 (18)	0.40302 (4)	0.42266 (15)	0.0290 (3)
O2	0.2633 (2)	0.34385 (4)	0.07577 (16)	0.0313 (3)
O1W	0.1024 (2)	0.37124 (8)	0.2330 (2)	0.0539 (5)
H1	0.189 (3)	0.3741 (11)	0.301 (3)	0.090 (14)*
H2	0.126 (4)	0.3598 (9)	0.176 (3)	0.062 (10)*
C1	0.6506 (2)	0.44805 (6)	0.4419 (2)	0.0233 (4)
C2	0.6694 (3)	0.41888 (7)	0.3542 (2)	0.0324 (5)
H2A	0.6044	0.3949	0.3272	0.039*
C3	0.7822 (3)	0.42496 (8)	0.3069 (3)	0.0454 (7)
H3	0.7941	0.4054	0.2466	0.055*
C4	0.8776 (3)	0.45964 (9)	0.3476 (3)	0.0485 (7)
H4	0.9556	0.4636	0.3154	0.058*
C5	0.8609 (3)	0.48886 (8)	0.4353 (3)	0.0407 (6)
H5	0.9275	0.5125	0.4633	0.049*
C6	0.7458 (2)	0.48303 (7)	0.4817 (2)	0.0303 (5)
H6	0.7325	0.5030	0.5405	0.036*
C7	0.3943 (2)	0.48571 (5)	0.4777 (2)	0.0211 (4)
C8	0.2742 (2)	0.49264 (7)	0.3473 (2)	0.0281 (5)
H8	0.2488	0.4719	0.2787	0.034*
C9	0.1909 (3)	0.53010 (7)	0.3171 (3)	0.0344 (5)
H9	0.1107	0.5352	0.2277	0.041*
C10	0.2272 (3)	0.55987 (6)	0.4198 (3)	0.0334 (6)
H10	0.1716	0.5855	0.4000	0.040*
C11	0.3420 (3)	0.55246 (7)	0.5488 (3)	0.0313 (5)
H11	0.3636	0.5727	0.6183	0.038*
C12	0.4276 (3)	0.51563 (6)	0.5793 (2)	0.0263 (4)
H12	0.5081	0.5109	0.6689	0.032*
C13	0.6082 (2)	0.42669 (6)	0.6805 (2)	0.0189 (4)
C14	0.5294 (2)	0.42678 (6)	0.7640 (2)	0.0245 (4)
H14	0.4233	0.4360	0.7282	0.029*
C15	0.6055 (3)	0.41348 (7)	0.8986 (2)	0.0283 (4)
H15	0.5518	0.4139	0.9551	0.034*
C16	0.7600 (3)	0.39947 (7)	0.9512 (2)	0.0303 (5)
H16	0.8118	0.3903	1.0434	0.036*
C17	0.8380 (2)	0.39900 (7)	0.8685 (2)	0.0280 (5)
H17	0.9434	0.3892	0.9045	0.034*
C18	0.7640 (2)	0.41266 (6)	0.7337 (2)	0.0238 (4)
H18	0.8188	0.4125	0.6780	0.029*
C19	0.4727 (2)	0.29581 (6)	0.02612 (19)	0.0229 (4)
C20	0.5931 (3)	0.32190 (7)	0.1102 (2)	0.0350 (5)
H20	0.5702	0.3463	0.1476	0.042*
C21	0.7491 (3)	0.31176 (9)	0.1393 (3)	0.0490 (7)
H21	0.8326	0.3293	0.1971	0.059*
C22	0.7812 (3)	0.27687 (9)	0.0848 (3)	0.0532 (8)
H22	0.8873	0.2706	0.1044	0.064*
C23	0.6632 (3)	0.25051 (8)	0.0020 (3)	0.0454 (6)
H23	0.6875	0.2261	−0.0341	0.054*
C24	0.5076 (2)	0.26023 (6)	−0.0279 (2)	0.0294 (5)
H24	0.4250	0.2424	−0.0855	0.035*
C25	0.1779 (2)	0.26268 (5)	0.0024 (2)	0.0205 (3)
C26	0.1924 (2)	0.25324 (6)	0.1333 (2)	0.0248 (4)
H26	0.2439	0.2721	0.2068	0.030*
C27	0.1310 (2)	0.21616 (6)	0.1556 (2)	0.0288 (4)
H27	0.1419	0.2096	0.2448	0.035*
C28	0.0546 (3)	0.18885 (6)	0.0493 (3)	0.0288 (5)
H28	0.0132	0.1636	0.0656	0.035*
C29	0.0377 (2)	0.19808 (6)	−0.0821 (2)	0.0249 (4)
H29	−0.0167	0.1794	−0.1555	0.030*
C30	0.1007 (2)	0.23465 (6)	−0.1051 (2)	0.0230 (4)
H30	0.0915	0.2407	−0.1941	0.028*
C31	0.1855 (2)	0.32405 (6)	−0.1932 (2)	0.0202 (4)
C32	0.0223 (2)	0.32522 (6)	−0.2683 (2)	0.0245 (4)
H32	−0.0436	0.3158	−0.2282	0.029*
C33	−0.0444 (3)	0.34019 (7)	−0.4020 (3)	0.0297 (5)
H33	−0.1555	0.3407	−0.4534	0.036*
C34	0.0521 (3)	0.35441 (7)	−0.4601 (2)	0.0283 (4)
H34	0.0063	0.3647	−0.5512	0.034*
C35	0.2138 (2)	0.35372 (6)	−0.3869 (2)	0.0249 (4)
H35	0.2791	0.3636	−0.4270	0.030*
C36	0.2802 (2)	0.33844 (6)	−0.2535 (2)	0.0225 (4)
H36	0.3915	0.3378	−0.2028	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0212 (3)	0.0158 (2)	0.0184 (2)	0.00008 (17)	0.00812 (19)	−0.00098 (18)
P2	0.0238 (3)	0.0167 (2)	0.0194 (3)	−0.00428 (18)	0.0110 (2)	−0.00323 (18)
O1	0.0326 (8)	0.0215 (6)	0.0255 (7)	−0.0022 (6)	0.0056 (6)	−0.0038 (6)
O2	0.0468 (9)	0.0238 (7)	0.0302 (8)	−0.0088 (6)	0.0232 (7)	−0.0084 (6)
O1W	0.0235 (9)	0.0977 (15)	0.0408 (9)	−0.0137 (10)	0.0144 (9)	−0.0238 (10)
C1	0.0262 (9)	0.0265 (9)	0.0214 (9)	0.0102 (7)	0.0143 (8)	0.0097 (7)
C2	0.0457 (13)	0.0306 (10)	0.0247 (10)	0.0165 (10)	0.0188 (10)	0.0090 (8)
C3	0.0653 (17)	0.0488 (15)	0.0371 (13)	0.0314 (13)	0.0361 (13)	0.0198 (12)
C4	0.0477 (15)	0.0674 (17)	0.0475 (15)	0.0333 (14)	0.0365 (13)	0.0341 (14)
C5	0.0314 (11)	0.0453 (13)	0.0510 (15)	0.0066 (10)	0.0231 (11)	0.0226 (12)
C6	0.0300 (12)	0.0303 (10)	0.0333 (11)	0.0069 (8)	0.0162 (10)	0.0107 (9)
C7	0.0211 (9)	0.0156 (8)	0.0291 (10)	0.0009 (6)	0.0131 (9)	0.0010 (8)
C8	0.0241 (10)	0.0280 (10)	0.0312 (11)	0.0055 (8)	0.0111 (9)	0.0009 (8)
C9	0.0243 (10)	0.0346 (11)	0.0415 (13)	0.0065 (9)	0.0115 (10)	0.0091 (10)
C10	0.0275 (12)	0.0197 (10)	0.0591 (16)	0.0041 (8)	0.0244 (11)	0.0075 (9)
C11	0.0319 (11)	0.0197 (9)	0.0502 (14)	−0.0025 (8)	0.0251 (11)	−0.0055 (9)
C12	0.0299 (10)	0.0210 (9)	0.0299 (11)	−0.0030 (8)	0.0148 (9)	−0.0021 (8)
C13	0.0222 (9)	0.0155 (8)	0.0180 (9)	−0.0035 (7)	0.0076 (8)	−0.0010 (7)
C14	0.0238 (9)	0.0262 (10)	0.0264 (10)	0.0004 (7)	0.0135 (8)	−0.0015 (8)
C15	0.0323 (11)	0.0327 (11)	0.0280 (10)	−0.0014 (9)	0.0208 (9)	0.0013 (9)
C16	0.0342 (11)	0.0332 (10)	0.0226 (10)	−0.0014 (9)	0.0116 (9)	0.0028 (8)
C17	0.0187 (9)	0.0354 (11)	0.0277 (11)	−0.0024 (8)	0.0080 (8)	0.0028 (9)
C18	0.0232 (9)	0.0280 (10)	0.0240 (10)	0.0002 (8)	0.0138 (8)	0.0039 (8)
C19	0.0184 (8)	0.0265 (9)	0.0196 (9)	−0.0039 (7)	0.0045 (7)	0.0076 (7)
C20	0.0317 (12)	0.0351 (11)	0.0275 (11)	−0.0132 (9)	0.0031 (10)	0.0088 (9)
C21	0.0240 (11)	0.0537 (16)	0.0466 (15)	−0.0151 (11)	−0.0058 (11)	0.0241 (12)
C22	0.0243 (11)	0.0564 (16)	0.0723 (19)	0.0065 (11)	0.0148 (12)	0.0419 (15)
C23	0.0337 (12)	0.0396 (12)	0.0683 (17)	0.0134 (10)	0.0273 (13)	0.0277 (13)
C24	0.0249 (10)	0.0292 (10)	0.0341 (12)	0.0042 (8)	0.0129 (9)	0.0092 (8)
C25	0.0193 (9)	0.0191 (8)	0.0232 (9)	−0.0012 (7)	0.0094 (8)	−0.0006 (8)
C26	0.0221 (9)	0.0283 (10)	0.0254 (10)	−0.0014 (8)	0.0117 (8)	0.0001 (8)
C27	0.0290 (10)	0.0292 (10)	0.0339 (11)	−0.0009 (9)	0.0191 (9)	0.0036 (9)
C28	0.0217 (10)	0.0204 (10)	0.0475 (14)	0.0015 (7)	0.0179 (9)	0.0040 (8)
C29	0.0204 (9)	0.0186 (9)	0.0322 (11)	0.0001 (7)	0.0082 (8)	−0.0022 (8)
C30	0.0222 (9)	0.0203 (9)	0.0245 (10)	0.0034 (7)	0.0082 (8)	−0.0010 (8)
C31	0.0218 (9)	0.0156 (8)	0.0213 (10)	0.0012 (7)	0.0076 (8)	−0.0012 (8)
C32	0.0207 (9)	0.0230 (10)	0.0314 (11)	−0.0001 (7)	0.0128 (8)	−0.0013 (8)
C33	0.0195 (9)	0.0297 (10)	0.0326 (11)	0.0015 (8)	0.0045 (9)	0.0017 (9)
C34	0.0304 (10)	0.0293 (10)	0.0214 (10)	0.0038 (8)	0.0076 (9)	0.0057 (8)
C35	0.0269 (10)	0.0268 (9)	0.0234 (10)	0.0010 (8)	0.0131 (9)	0.0035 (8)
C36	0.0191 (9)	0.0235 (9)	0.0246 (10)	−0.0007 (7)	0.0093 (8)	−0.0011 (8)

Geometric parameters (Å, º) top

P1—O1	1.4871 (15)	C16—C17	1.385 (3)
P1—C1	1.801 (2)	C16—H16	0.9500
P1—C7	1.8035 (18)	C17—C18	1.390 (3)
P1—C13	1.805 (2)	C17—H17	0.9500
P2—O2	1.4985 (14)	C18—H18	0.9500
P2—C31	1.799 (2)	C19—C20	1.388 (3)
P2—C25	1.8051 (19)	C19—C24	1.390 (3)
P2—C19	1.8076 (19)	C20—C21	1.402 (4)
O1W—H1	0.84 (3)	C20—H20	0.9500
O1W—H2	0.83 (3)	C21—C22	1.363 (4)
C1—C6	1.387 (3)	C21—H21	0.9500
C1—C2	1.401 (3)	C22—C23	1.377 (4)
C2—C3	1.381 (4)	C22—H22	0.9500
C2—H2A	0.9500	C23—C24	1.394 (3)
C3—C4	1.381 (4)	C23—H23	0.9500
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.395 (4)	C25—C26	1.399 (3)
C4—H4	0.9500	C25—C30	1.402 (3)
C5—C6	1.394 (3)	C26—C27	1.393 (3)
C5—H5	0.9500	C26—H26	0.9500
C6—H6	0.9500	C27—C28	1.378 (3)
C7—C12	1.393 (3)	C27—H27	0.9500
C7—C8	1.394 (3)	C28—C29	1.395 (3)
C8—C9	1.398 (3)	C28—H28	0.9500
C8—H8	0.9500	C29—C30	1.389 (3)
C9—C10	1.395 (4)	C29—H29	0.9500
C9—H9	0.9500	C30—H30	0.9500
C10—C11	1.367 (4)	C31—C32	1.395 (3)
C10—H10	0.9500	C31—C36	1.395 (3)
C11—C12	1.391 (3)	C32—C33	1.392 (3)
C11—H11	0.9500	C32—H32	0.9500
C12—H12	0.9500	C33—C34	1.390 (3)
C13—C14	1.398 (3)	C33—H33	0.9500
C13—C18	1.400 (3)	C34—C35	1.379 (3)
C14—C15	1.385 (3)	C34—H34	0.9500
C14—H14	0.9500	C35—C36	1.393 (3)
C15—C16	1.389 (3)	C35—H35	0.9500
C15—H15	0.9500	C36—H36	0.9500

O1—P1—C1	111.49 (10)	C16—C17—C18	120.80 (19)
O1—P1—C7	111.83 (9)	C16—C17—H17	119.6
C1—P1—C7	105.96 (9)	C18—C17—H17	119.6
O1—P1—C13	112.48 (9)	C17—C18—C13	119.51 (18)
C1—P1—C13	105.40 (9)	C17—C18—H18	120.2
C7—P1—C13	109.28 (9)	C13—C18—H18	120.2
O2—P2—C31	113.00 (9)	C20—C19—C24	119.9 (2)
O2—P2—C25	112.26 (9)	C20—C19—P2	118.93 (17)
C31—P2—C25	108.33 (9)	C24—C19—P2	121.10 (15)
O2—P2—C19	111.57 (10)	C19—C20—C21	119.1 (2)
C31—P2—C19	105.30 (9)	C19—C20—H20	120.5
C25—P2—C19	105.90 (9)	C21—C20—H20	120.5
H1—O1W—H2	104 (3)	C22—C21—C20	120.2 (2)
C6—C1—C2	120.0 (2)	C22—C21—H21	119.9
C6—C1—P1	122.44 (15)	C20—C21—H21	119.9
C2—C1—P1	117.53 (17)	C21—C22—C23	121.4 (2)
C3—C2—C1	120.1 (2)	C21—C22—H22	119.3
C3—C2—H2A	119.9	C23—C22—H22	119.3
C1—C2—H2A	119.9	C22—C23—C24	119.0 (3)
C4—C3—C2	119.8 (2)	C22—C23—H23	120.5
C4—C3—H3	120.1	C24—C23—H23	120.5
C2—C3—H3	120.1	C19—C24—C23	120.4 (2)
C3—C4—C5	120.8 (2)	C19—C24—H24	119.8
C3—C4—H4	119.6	C23—C24—H24	119.8
C5—C4—H4	119.6	C26—C25—C30	119.38 (18)
C6—C5—C4	119.5 (2)	C26—C25—P2	116.88 (15)
C6—C5—H5	120.3	C30—C25—P2	123.64 (16)
C4—C5—H5	120.3	C27—C26—C25	119.83 (19)
C1—C6—C5	119.8 (2)	C27—C26—H26	120.1
C1—C6—H6	120.1	C25—C26—H26	120.1
C5—C6—H6	120.1	C28—C27—C26	120.5 (2)
C12—C7—C8	119.78 (18)	C28—C27—H27	119.8
C12—C7—P1	124.40 (16)	C26—C27—H27	119.8
C8—C7—P1	115.79 (16)	C27—C28—C29	120.29 (19)
C7—C8—C9	120.1 (2)	C27—C28—H28	119.9
C7—C8—H8	119.9	C29—C28—H28	119.9
C9—C8—H8	119.9	C30—C29—C28	119.7 (2)
C10—C9—C8	119.2 (2)	C30—C29—H29	120.1
C10—C9—H9	120.4	C28—C29—H29	120.1
C8—C9—H9	120.4	C29—C30—C25	120.2 (2)
C11—C10—C9	120.5 (2)	C29—C30—H30	119.9
C11—C10—H10	119.8	C25—C30—H30	119.9
C9—C10—H10	119.8	C32—C31—C36	119.09 (18)
C10—C11—C12	120.8 (2)	C32—C31—P2	120.15 (16)
C10—C11—H11	119.6	C36—C31—P2	120.39 (15)
C12—C11—H11	119.6	C33—C32—C31	120.15 (19)
C11—C12—C7	119.5 (2)	C33—C32—H32	119.9
C11—C12—H12	120.2	C31—C32—H32	119.9
C7—C12—H12	120.2	C34—C33—C32	119.85 (19)
C14—C13—C18	119.49 (18)	C34—C33—H33	120.1
C14—C13—P1	120.00 (15)	C32—C33—H33	120.1
C18—C13—P1	119.98 (15)	C35—C34—C33	120.7 (2)
C15—C14—C13	120.22 (18)	C35—C34—H34	119.6
C15—C14—H14	119.9	C33—C34—H34	119.6
C13—C14—H14	119.9	C34—C35—C36	119.32 (19)
C14—C15—C16	120.29 (19)	C34—C35—H35	120.3
C14—C15—H15	119.9	C36—C35—H35	120.3
C16—C15—H15	119.9	C35—C36—C31	120.85 (18)
C17—C16—C15	119.7 (2)	C35—C36—H36	119.6
C17—C16—H16	120.2	C31—C36—H36	119.6
C15—C16—H16	120.2

O1—P1—C1—C6	169.22 (16)	O2—P2—C19—C20	−13.47 (18)
C7—P1—C1—C6	47.3 (2)	C31—P2—C19—C20	109.47 (17)
C13—P1—C1—C6	−68.45 (18)	C25—P2—C19—C20	−135.89 (16)
O1—P1—C1—C2	−11.38 (19)	O2—P2—C19—C24	168.31 (15)
C7—P1—C1—C2	−133.27 (16)	C31—P2—C19—C24	−68.75 (17)
C13—P1—C1—C2	110.95 (17)	C25—P2—C19—C24	45.89 (19)
C6—C1—C2—C3	−0.2 (3)	C24—C19—C20—C21	0.0 (3)
P1—C1—C2—C3	−179.65 (16)	P2—C19—C20—C21	−178.23 (18)
C1—C2—C3—C4	0.8 (3)	C19—C20—C21—C22	0.4 (3)
C2—C3—C4—C5	−0.4 (4)	C20—C21—C22—C23	−0.9 (4)
C3—C4—C5—C6	−0.4 (3)	C21—C22—C23—C24	0.9 (4)
C2—C1—C6—C5	−0.6 (3)	C20—C19—C24—C23	0.1 (3)
P1—C1—C6—C5	178.78 (16)	P2—C19—C24—C23	178.29 (18)
C4—C5—C6—C1	0.9 (3)	C22—C23—C24—C19	−0.6 (4)
O1—P1—C7—C12	144.49 (16)	O2—P2—C25—C26	−35.86 (18)
C1—P1—C7—C12	−93.83 (18)	C31—P2—C25—C26	−161.33 (15)
C13—P1—C7—C12	19.28 (19)	C19—P2—C25—C26	86.12 (16)
O1—P1—C7—C8	−37.70 (19)	O2—P2—C25—C30	147.75 (16)
C1—P1—C7—C8	83.97 (17)	C31—P2—C25—C30	22.27 (18)
C13—P1—C7—C8	−162.91 (15)	C19—P2—C25—C30	−90.28 (17)
C12—C7—C8—C9	2.2 (3)	C30—C25—C26—C27	0.3 (3)
P1—C7—C8—C9	−175.69 (16)	P2—C25—C26—C27	−176.21 (15)
C7—C8—C9—C10	−1.5 (3)	C25—C26—C27—C28	−0.7 (3)
C8—C9—C10—C11	−0.4 (3)	C26—C27—C28—C29	0.0 (3)
C9—C10—C11—C12	1.6 (3)	C27—C28—C29—C30	1.1 (3)
C10—C11—C12—C7	−0.9 (3)	C28—C29—C30—C25	−1.5 (3)
C8—C7—C12—C11	−1.0 (3)	C26—C25—C30—C29	0.7 (3)
P1—C7—C12—C11	176.70 (16)	P2—C25—C30—C29	177.05 (15)
O1—P1—C13—C14	−73.10 (19)	O2—P2—C31—C32	−76.16 (18)
C1—P1—C13—C14	165.21 (16)	C25—P2—C31—C32	48.88 (18)
C7—P1—C13—C14	51.73 (19)	C19—P2—C31—C32	161.83 (16)
O1—P1—C13—C18	98.50 (17)	O2—P2—C31—C36	96.75 (17)
C1—P1—C13—C18	−23.18 (19)	C25—P2—C31—C36	−138.21 (16)
C7—P1—C13—C18	−136.67 (16)	C19—P2—C31—C36	−25.27 (18)
C18—C13—C14—C15	0.6 (3)	C36—C31—C32—C33	0.6 (3)
P1—C13—C14—C15	172.26 (16)	P2—C31—C32—C33	173.60 (16)
C13—C14—C15—C16	−0.8 (3)	C31—C32—C33—C34	−0.7 (3)
C14—C15—C16—C17	0.2 (3)	C32—C33—C34—C35	0.2 (3)
C15—C16—C17—C18	0.5 (3)	C33—C34—C35—C36	0.2 (3)
C16—C17—C18—C13	−0.6 (3)	C34—C35—C36—C31	−0.3 (3)
C14—C13—C18—C17	0.1 (3)	C32—C31—C36—C35	−0.1 (3)
P1—C13—C18—C17	−171.57 (16)	P2—C31—C36—C35	−173.12 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O1	0.84 (3)	2.05 (2)	2.836 (2)	156 (4)
O1w—H2···O2	0.83 (3)	2.09 (2)	2.870 (2)	158 (3)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅OP·0.5H₂O
M_r	287.28
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	9.4313 (1), 32.1930 (4), 10.8435 (1)
β (°)	115.742 (1)
V (Å³)	2965.59 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	14206, 6609, 6504
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.065, 1.02
No. of reflections	6609
No. of parameters	379
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.17
Absolute structure	Flack (1983), 3203 Friedel pairs
Absolute structure parameter	0.02 (5)

Computer programs: APEX2 (Bruker, 2008) [Au SMART software for SMART machine?], APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O1	0.84 (3)	2.05 (2)	2.836 (2)	156 (4)
O1w—H2···O2	0.83 (3)	2.09 (2)	2.870 (2)	158 (3)

Acknowledgements

The author thanks the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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