A second monoclinic modification of triphenyl-phosphine oxide hemihydrate.

In the crystal of the title compound, C(18)H(15)OP·0.5H(2)O, 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 = 287.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.065

S = 1.02

6609 reflections

379 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 3203 Friedel pairs

Flack parameter: 0.02 (5)

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 ▶).

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

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

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

C18H15OP·0.5H2O	F(000) = 1208
Mr = 287.28	Dx = 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

Bruker SMART APEX diffractometer	6609 independent reflections
Radiation source: fine-focus sealed tube	6504 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.947, Tmax = 0.965	k = −41→41
14206 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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
6609 reflections	Δρmax = 0.24 e Å−3
379 parameters	Δρmin = −0.17 e Å−3
4 restraints	Absolute structure: Flack (1983), 3203 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (5)

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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)