(Benzoyl­methyl)­tri­phenyl­phospho­nium iodide: supramolecular zigzag chains via C—H...O hydrogen bonding stabilized by C—H...I interactions

The title phospho­nium salt, C₂₆H₂₂OP⁺·I⁻, isomorphous with (benzoyl­methyl)­tri­phenyl­phospho­nium nitrate, exhibits both intramolecular C—H...I and intermolecular C—H...O interactions. The latter interaction leads to supramolecular parallel zigzag chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.057
• Data-to-parameter ratio = 16.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Phosphonium keto ylides react with metal salts to form not only ylide complexes but also phosphonium salts (Antipin et al., 1984; Baby Mariyatra et al., 2002) and phosphonium metalates (Albanese et al., 1989; Bart et al.,1982). The action of trimethyltin chloride on (benzoylmethylene)triphenylphosphorane led to the first O-coordinated ketoylide complex (Buckel et al., 1972). The reaction of SnI₄ with the same ylide was performed to prepare a six-coordinate complex, containing the ylide. However, the above reaction in benzene yielded the product of composition [(C₆H₅)₃PCH₂COPh]₂[SnI₆], as revealed by its elemental analysis (analysis found: C 37.98, H 2.78%; calculated: C 38.01, H 2.70%). The product was recrystallized from methanol. Its ¹H NMR in CDCl₃ indicates that it is a phosphonium salt different from the initial phosphonium metalate. The investigation reported herein has been undertaken to assign the molecular and supramolecular structure of the title compound, (I).

The molecular structure of (I) is unexceptional and formed by the C protonation of the parent ylide. It is confirmed that compound (I) is an ion pair (Fig. 1) with a distance of 4.6231 (7) Å between the P⁺ and I⁻ centers. The metrical parameters in (I) resemble those of the isomorphous nitrate salt (Pbca with Z = 8; Baby Mariyatra et al., 2002), but differ from the parent ylide (Kalyanasundari et al., 1994). The crystal structure can be best described as a zigzag chain formed by C—H···O hydrogen-bonding interactions (Table 2 and Fig. 2). The H1—C1—C2—O1 torsion angle [145.4 (14)°] indicates that atoms H1 and O1 are considerably distorted from an antiperiplanar arrangement, as expected for the formation of a zigzag chain. The I⁻ ions are embedded in the space between the chains and contribute to the three -dimensional arrangement via three C—H···I interactions (Table 2 and Fig. 3). The C···I distances [3.696 (2), 3.802 (2) and 3.983 (2) Å] are comparable to those observed in the fulleride salt [(C₆H₅)₄P]₂(C₆₀)I_0.35 (C···I⁻ = 3.67 Å; Penicaud et al., 1993) and those observed in (α-ferrocenylphenacyl)triphenylphosphonium iodide [C···I = 3.836 (7), 3.932 (7) and 3.995 (7) Å; Ahmed et al., 1996].

The present results indicate that the phosphonium salt is present in the C-protonated form both in solution and solid state. The ylidic C atom is involved in hydrogen-bonding interactions, as observed in many similar structures (Yufit et al., 2000; Baby Mariyatra et al., 2002). We attribute the predominance of the C-protonated form to the considerable carbanionic character of the ylidic C atom in spite of resonance stabilization.

S2. Experimental

The title phosphonium salt, (I), was obtained when the product of the reaction between stannic iodide and the phosphonium ylide, (benzoylmethylene)triphenylphosphorane was crystallized in dry methanol.

S3. Refinement

All the H atoms were located from difference Fourier maps and their positional and U_iso parameters were refined. The C—H bond distances range from 0.91 (3) to 0.98 (2) Å.

Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of the title compound, (I), showing 50% probability displacement ellipsoids.
	Fig. 2. View of the chain along the a axis due to a C—H···O interaction.
	Fig. 3. Diagram showing both the C—H···I and C—H···O interactions.

(Benzoylmethyl)triphenylphosphonium iodide

Crystal data

C26H22OP^+·I^−	Dx = 1.482 Mg m^−3
Mr = 508.31	Melting point: decomposes above 473 K K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 10.870 (2) Å	Cell parameters from 805 reflections
b = 18.932 (2) Å	θ = 10.2–23.6°
c = 22.135 (3) Å	µ = 1.49 mm^−1
V = 4555.2 (11) Å^3	T = 120 K
Z = 8	Block, light yellow
F(000) = 2032	0.46 × 0.32 × 0.28 mm

Data collection

Bruker SMART 1K CCD diffractometer	5663 independent reflections
Radiation source: fine-focus sealed tube	4873 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: integration (XPREP in SHELXTL; Bruker, 1998)	h = −13→14
Tmin = 0.555, Tmax = 0.684	k = −25→24
29262 measured reflections	l = −29→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: difference Fourier map
wR(F^2) = 0.057	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0193P)^2 + 4.7P] where P = (Fo^2 + 2Fc^2)/3
5663 reflections	(Δ/σ)max = 0.002
350 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.74 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.340625 (13)	0.346975 (7)	0.393471 (6)	0.02309 (5)
P1	0.37220 (5)	0.11545 (3)	0.32890 (2)	0.01544 (10)
O1	0.20335 (14)	0.17728 (8)	0.23889 (7)	0.0244 (3)
C1	0.39361 (19)	0.19780 (10)	0.28896 (9)	0.0170 (4)
H1	0.478 (2)	0.1994 (11)	0.2761 (10)	0.019 (6)*
H2	0.383 (2)	0.2342 (14)	0.3157 (12)	0.034 (7)*
C2	0.30185 (18)	0.20869 (10)	0.23813 (9)	0.0177 (4)
C3	0.33438 (19)	0.25922 (10)	0.18899 (9)	0.0197 (4)
C4	0.2558 (2)	0.26312 (12)	0.13911 (10)	0.0258 (5)
H4	0.186 (2)	0.2312 (14)	0.1372 (12)	0.034 (7)*
C5	0.2815 (2)	0.30947 (14)	0.09199 (11)	0.0325 (5)
H5	0.228 (3)	0.3097 (15)	0.0574 (13)	0.045 (8)*
C6	0.3850 (3)	0.35259 (13)	0.09479 (12)	0.0347 (6)
H6	0.405 (3)	0.3839 (15)	0.0630 (13)	0.041 (8)*
C7	0.4641 (2)	0.34901 (13)	0.14419 (11)	0.0313 (5)
H7	0.534 (2)	0.3784 (13)	0.1459 (11)	0.028 (6)*
C8	0.4391 (2)	0.30237 (11)	0.19148 (10)	0.0241 (4)
H8	0.492 (2)	0.3014 (13)	0.2254 (12)	0.030 (7)*
C11	0.50269 (18)	0.10598 (10)	0.37836 (9)	0.0177 (4)
C12	0.5937 (2)	0.05561 (12)	0.36804 (10)	0.0256 (5)
H12	0.587 (2)	0.0254 (14)	0.3328 (12)	0.038 (7)*
C13	0.6922 (2)	0.04983 (15)	0.40828 (11)	0.0346 (6)
H13	0.753 (3)	0.0162 (14)	0.4016 (12)	0.039 (8)*
C14	0.6987 (2)	0.09405 (13)	0.45788 (11)	0.0285 (5)
H14	0.760 (3)	0.0901 (14)	0.4868 (12)	0.038 (7)*
C15	0.6084 (2)	0.14484 (12)	0.46803 (10)	0.0251 (4)
H15	0.613 (2)	0.1744 (13)	0.5013 (11)	0.026 (6)*
C16	0.5098 (2)	0.15087 (11)	0.42866 (9)	0.0221 (4)
H16	0.449 (2)	0.1855 (13)	0.4347 (11)	0.029 (7)*
C21	0.23968 (18)	0.11510 (10)	0.37758 (9)	0.0173 (4)
C22	0.15386 (19)	0.17010 (11)	0.37802 (10)	0.0215 (4)
H22	0.161 (2)	0.2094 (13)	0.3497 (11)	0.025 (6)*
C23	0.0595 (2)	0.17014 (12)	0.42064 (11)	0.0262 (5)
H23	0.005 (2)	0.2089 (13)	0.4204 (11)	0.029 (7)*
C24	0.0512 (2)	0.11619 (13)	0.46268 (10)	0.0277 (5)
H24	−0.009 (2)	0.1188 (13)	0.4916 (12)	0.032 (7)*
C25	0.1358 (2)	0.06123 (13)	0.46219 (10)	0.0277 (5)
H25	0.129 (2)	0.0259 (13)	0.4901 (12)	0.029 (7)*
C26	0.2311 (2)	0.06032 (11)	0.42026 (10)	0.0232 (4)
H26	0.290 (2)	0.0229 (12)	0.4199 (10)	0.018 (6)*
C31	0.37251 (18)	0.04508 (10)	0.27484 (9)	0.0174 (4)
C32	0.2969 (2)	−0.01413 (11)	0.28208 (10)	0.0232 (4)
H32	0.243 (2)	−0.0173 (12)	0.3164 (11)	0.023 (6)*
C33	0.3046 (2)	−0.06942 (12)	0.24049 (11)	0.0301 (5)
H33	0.256 (2)	−0.1086 (13)	0.2457 (12)	0.032 (7)*
C34	0.3869 (2)	−0.06619 (12)	0.19311 (11)	0.0275 (5)
H34	0.394 (2)	−0.1038 (13)	0.1675 (11)	0.028 (7)*
C35	0.4615 (2)	−0.00716 (12)	0.18558 (10)	0.0269 (5)
H35	0.520 (3)	−0.0065 (14)	0.1517 (12)	0.037 (7)*
C36	0.4551 (2)	0.04867 (12)	0.22622 (10)	0.0240 (4)
H36	0.506 (2)	0.0881 (13)	0.2208 (12)	0.034 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02751 (8)	0.02053 (7)	0.02123 (7)	−0.00078 (5)	0.00089 (5)	−0.00326 (5)
P1	0.0140 (2)	0.0163 (2)	0.0160 (2)	−0.00006 (18)	0.00037 (18)	−0.00063 (18)
O1	0.0183 (7)	0.0290 (8)	0.0261 (8)	−0.0041 (6)	−0.0024 (6)	0.0027 (6)
C1	0.0169 (10)	0.0165 (9)	0.0178 (9)	−0.0009 (7)	−0.0006 (7)	0.0001 (7)
C2	0.0168 (9)	0.0176 (9)	0.0186 (10)	0.0012 (7)	0.0009 (7)	−0.0028 (7)
C3	0.0201 (10)	0.0194 (9)	0.0196 (10)	0.0036 (8)	0.0028 (8)	−0.0005 (7)
C4	0.0240 (11)	0.0295 (12)	0.0240 (11)	0.0030 (9)	−0.0017 (9)	0.0017 (9)
C5	0.0359 (14)	0.0373 (13)	0.0243 (12)	0.0095 (11)	−0.0013 (10)	0.0048 (10)
C6	0.0392 (14)	0.0336 (13)	0.0312 (13)	0.0102 (11)	0.0125 (10)	0.0116 (10)
C7	0.0296 (12)	0.0295 (12)	0.0348 (13)	−0.0007 (10)	0.0088 (10)	0.0080 (10)
C8	0.0233 (11)	0.0227 (10)	0.0262 (11)	−0.0001 (8)	0.0019 (9)	0.0017 (8)
C11	0.0151 (9)	0.0225 (9)	0.0155 (9)	−0.0006 (7)	−0.0006 (7)	0.0021 (7)
C12	0.0240 (11)	0.0294 (11)	0.0235 (11)	0.0074 (9)	−0.0018 (9)	−0.0062 (9)
C13	0.0248 (12)	0.0458 (15)	0.0333 (13)	0.0165 (11)	−0.0057 (10)	−0.0089 (11)
C14	0.0213 (11)	0.0394 (13)	0.0248 (11)	0.0034 (9)	−0.0074 (9)	−0.0018 (10)
C15	0.0246 (11)	0.0309 (11)	0.0199 (10)	−0.0009 (9)	−0.0021 (8)	−0.0034 (9)
C16	0.0206 (10)	0.0246 (10)	0.0212 (10)	0.0024 (9)	−0.0009 (8)	−0.0026 (8)
C21	0.0161 (9)	0.0198 (9)	0.0162 (9)	0.0003 (7)	0.0016 (7)	−0.0027 (7)
C22	0.0210 (10)	0.0200 (9)	0.0233 (10)	0.0012 (8)	0.0001 (8)	−0.0004 (8)
C23	0.0186 (11)	0.0299 (12)	0.0300 (12)	0.0051 (9)	0.0031 (9)	−0.0048 (9)
C24	0.0178 (11)	0.0410 (13)	0.0243 (11)	−0.0037 (9)	0.0057 (9)	−0.0045 (10)
C25	0.0271 (12)	0.0348 (12)	0.0213 (11)	−0.0028 (9)	0.0046 (9)	0.0049 (9)
C26	0.0217 (11)	0.0243 (11)	0.0235 (11)	0.0018 (9)	0.0020 (8)	0.0020 (8)
C31	0.0173 (9)	0.0174 (9)	0.0174 (9)	0.0010 (7)	−0.0018 (7)	−0.0025 (7)
C32	0.0226 (10)	0.0223 (10)	0.0247 (11)	−0.0027 (8)	0.0031 (8)	−0.0007 (8)
C33	0.0288 (12)	0.0234 (11)	0.0380 (14)	−0.0079 (9)	−0.0008 (10)	−0.0067 (10)
C34	0.0270 (12)	0.0264 (11)	0.0292 (12)	0.0028 (9)	−0.0052 (9)	−0.0106 (9)
C35	0.0240 (11)	0.0334 (12)	0.0231 (11)	0.0021 (9)	0.0033 (9)	−0.0069 (9)
C36	0.0239 (11)	0.0252 (11)	0.0230 (11)	−0.0041 (9)	0.0037 (8)	−0.0023 (8)

Geometric parameters (Å, º)

P1—C31	1.791 (2)	C14—H14	0.93 (3)
P1—C21	1.799 (2)	C15—C16	1.386 (3)
P1—C11	1.801 (2)	C15—H15	0.93 (3)
P1—C1	1.807 (2)	C16—H16	0.94 (3)
O1—C2	1.225 (2)	C21—C22	1.398 (3)
C1—C2	1.518 (3)	C21—C26	1.406 (3)
C1—H1	0.96 (2)	C22—C23	1.393 (3)
C1—H2	0.92 (3)	C22—H22	0.98 (2)
C2—C3	1.491 (3)	C23—C24	1.385 (3)
C3—C4	1.398 (3)	C23—H23	0.94 (3)
C3—C8	1.402 (3)	C24—C25	1.389 (3)
C4—C5	1.391 (3)	C24—H24	0.92 (3)
C4—H4	0.97 (3)	C25—C26	1.391 (3)
C5—C6	1.392 (4)	C25—H25	0.91 (3)
C5—H5	0.96 (3)	C26—H26	0.95 (2)
C6—C7	1.393 (4)	C31—C32	1.399 (3)
C6—H6	0.95 (3)	C31—C36	1.403 (3)
C7—C8	1.396 (3)	C32—C33	1.396 (3)
C7—H7	0.94 (3)	C32—H32	0.96 (2)
C8—H8	0.95 (3)	C33—C34	1.380 (3)
C11—C12	1.393 (3)	C33—H33	0.92 (3)
C11—C16	1.403 (3)	C34—C35	1.391 (3)
C12—C13	1.397 (3)	C34—H34	0.91 (3)
C12—H12	0.97 (3)	C35—C36	1.390 (3)
C13—C14	1.383 (3)	C35—H35	0.98 (3)
C13—H13	0.93 (3)	C36—H36	0.94 (3)
C14—C15	1.393 (3)
C31—P1—C21	113.51 (9)	C15—C14—H14	116.8 (17)
C31—P1—C11	109.32 (9)	C16—C15—C14	120.1 (2)
C21—P1—C11	105.44 (9)	C16—C15—H15	119.6 (16)
C31—P1—C1	108.33 (9)	C14—C15—H15	120.3 (16)
C21—P1—C1	113.53 (9)	C15—C16—C11	119.4 (2)
C11—P1—C1	106.37 (9)	C15—C16—H16	120.7 (16)
C2—C1—P1	113.28 (14)	C11—C16—H16	119.9 (16)
C2—C1—H1	113.8 (14)	C22—C21—C26	120.05 (19)
P1—C1—H1	107.1 (13)	C22—C21—P1	122.39 (15)
C2—C1—H2	107.3 (17)	C26—C21—P1	117.26 (15)
P1—C1—H2	108.5 (16)	C23—C22—C21	119.7 (2)
H1—C1—H2	107 (2)	C23—C22—H22	119.5 (14)
O1—C2—C3	121.92 (18)	C21—C22—H22	120.7 (14)
O1—C2—C1	119.90 (18)	C24—C23—C22	120.2 (2)
C3—C2—C1	118.17 (17)	C24—C23—H23	122.4 (15)
C4—C3—C8	119.8 (2)	C22—C23—H23	117.4 (15)
C4—C3—C2	117.71 (19)	C23—C24—C25	120.3 (2)
C8—C3—C2	122.52 (19)	C23—C24—H24	118.4 (16)
C5—C4—C3	120.2 (2)	C25—C24—H24	121.3 (16)
C5—C4—H4	121.1 (16)	C24—C25—C26	120.5 (2)
C3—C4—H4	118.6 (16)	C24—C25—H25	119.5 (16)
C4—C5—C6	119.9 (2)	C26—C25—H25	119.9 (16)
C4—C5—H5	118.4 (17)	C25—C26—C21	119.2 (2)
C6—C5—H5	121.6 (17)	C25—C26—H26	121.0 (14)
C5—C6—C7	120.4 (2)	C21—C26—H26	119.8 (14)
C5—C6—H6	121.3 (18)	C32—C31—C36	120.17 (19)
C7—C6—H6	118.3 (18)	C32—C31—P1	121.23 (16)
C6—C7—C8	119.9 (2)	C36—C31—P1	118.53 (15)
C6—C7—H7	120.0 (16)	C33—C32—C31	119.3 (2)
C8—C7—H7	120.1 (16)	C33—C32—H32	120.7 (14)
C7—C8—C3	119.8 (2)	C31—C32—H32	119.9 (14)
C7—C8—H8	119.2 (15)	C34—C33—C32	120.5 (2)
C3—C8—H8	120.9 (15)	C34—C33—H33	120.2 (17)
C12—C11—C16	120.40 (19)	C32—C33—H33	119.3 (17)
C12—C11—P1	121.86 (16)	C33—C34—C35	120.3 (2)
C16—C11—P1	117.74 (15)	C33—C34—H34	119.3 (16)
C11—C12—C13	119.6 (2)	C35—C34—H34	120.4 (16)
C11—C12—H12	118.7 (16)	C36—C35—C34	120.3 (2)
C13—C12—H12	121.8 (16)	C36—C35—H35	121.1 (16)
C14—C13—C12	119.9 (2)	C34—C35—H35	118.6 (16)
C14—C13—H13	120.2 (17)	C35—C36—C31	119.4 (2)
C12—C13—H13	119.9 (17)	C35—C36—H36	119.5 (16)
C13—C14—C15	120.7 (2)	C31—C36—H36	121.0 (16)
C13—C14—H14	122.5 (17)
C31—P1—C1—C2	53.60 (16)	P1—C11—C16—C15	179.53 (17)
C21—P1—C1—C2	−73.47 (16)	C31—P1—C21—C22	−116.56 (18)
C11—P1—C1—C2	171.02 (14)	C11—P1—C21—C22	123.80 (18)
P1—C1—C2—O1	22.6 (2)	C1—P1—C21—C22	7.7 (2)
P1—C1—C2—C3	−158.66 (14)	C31—P1—C21—C26	69.73 (18)
O1—C2—C3—C4	−8.2 (3)	C11—P1—C21—C26	−49.90 (18)
C1—C2—C3—C4	173.10 (18)	C1—P1—C21—C26	−165.96 (16)
O1—C2—C3—C8	171.43 (19)	C26—C21—C22—C23	−0.4 (3)
C1—C2—C3—C8	−7.3 (3)	P1—C21—C22—C23	−173.94 (17)
C8—C3—C4—C5	0.2 (3)	C21—C22—C23—C24	0.4 (3)
C2—C3—C4—C5	179.9 (2)	C22—C23—C24—C25	−0.8 (3)
C3—C4—C5—C6	−0.7 (4)	C23—C24—C25—C26	1.1 (4)
C4—C5—C6—C7	0.8 (4)	C24—C25—C26—C21	−1.1 (3)
C5—C6—C7—C8	−0.5 (4)	C22—C21—C26—C25	0.7 (3)
C6—C7—C8—C3	0.1 (3)	P1—C21—C26—C25	174.60 (17)
C4—C3—C8—C7	0.1 (3)	C21—P1—C31—C32	−17.3 (2)
C2—C3—C8—C7	−179.6 (2)	C11—P1—C31—C32	100.12 (18)
C31—P1—C11—C12	7.4 (2)	C1—P1—C31—C32	−144.36 (17)
C21—P1—C11—C12	129.79 (18)	C21—P1—C31—C36	165.93 (16)
C1—P1—C11—C12	−109.35 (19)	C11—P1—C31—C36	−76.67 (18)
C31—P1—C11—C16	−171.95 (16)	C1—P1—C31—C36	38.85 (19)
C21—P1—C11—C16	−49.58 (18)	C36—C31—C32—C33	0.0 (3)
C1—P1—C11—C16	71.28 (18)	P1—C31—C32—C33	−176.74 (18)
C16—C11—C12—C13	0.2 (3)	C31—C32—C33—C34	0.7 (4)
P1—C11—C12—C13	−179.13 (19)	C32—C33—C34—C35	−1.2 (4)
C11—C12—C13—C14	−0.1 (4)	C33—C34—C35—C36	0.9 (4)
C12—C13—C14—C15	−0.5 (4)	C34—C35—C36—C31	−0.2 (3)
C13—C14—C15—C16	0.8 (4)	C32—C31—C36—C35	−0.3 (3)
C14—C15—C16—C11	−0.7 (3)	P1—C31—C36—C35	176.56 (17)
C12—C11—C16—C15	0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1^i	0.96 (2)	2.50 (2)	3.445 (3)	165.2 (18)
C1—H2···I1	0.92 (3)	2.78 (3)	3.696 (2)	177 (2)
C14—H14···I1^ii	0.93 (3)	3.03 (3)	3.802 (2)	141 (2)
C24—H24···I1^iii	0.92 (3)	3.09 (3)	3.983 (2)	164 (2)

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x+1/2, −y+1/2, −z+1; (iii) x−1/2, −y+1/2, −z+1.