Benzhydryl phenyl sulfone

Baidya, M.; Mayr, H.; Mayer, P.

doi:10.1107/S1600536809050363

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3224

doi:10.1107/S1600536809050363

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Benzhydryl phenyl sulfone

Mahiuddin Baidya,^a Herbert Mayr ^a and Peter Mayer ^a ^*

^aLudwig-Maximilians-Universität, Department, Butenandtstrasse 5–13, 81377 München, Germany
^*Correspondence e-mail: pemay@cup.uni-muenchen.de

(Received 3 November 2009; accepted 23 November 2009; online 28 November 2009)

In the title compound, C₁₉H₁₆O₂S, the sulfur-bound phenyl group is approximately parallel to one of the two phenyl rings of the benzhydryl group, making a dihedral angle of 12.53 (10)°, and forms a dihedral angle of 41.25 (9)° with the other phenyl ring. In the crystal, weak C—H⋯O interactions form a two-dimensional network propagating along the bc plane.

Related literature

For background to the sulfone anion, see: da Silva Corrêa et al. (1968 ); Mayr et al. (2001 , 2008 ). For a related structure, see: Li et al. (2005 ). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ); Etter et al. (1990 ).

Experimental

Crystal data

C₁₉H₁₆O₂S
M_r = 308.40
Orthorhombic, P c a 2₁
a = 16.3250 (4) Å
b = 5.7979 (1) Å
c = 16.4983 (4) Å
V = 1561.58 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 200 K
0.20 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
11675 measured reflections
3499 independent reflections
3136 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.075
S = 1.04
3499 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1646 Friedel pairs
Flack parameter: −0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	1.00	2.46	3.449 (2)	171
C4—H4⋯O1ⁱⁱ	0.95	2.66	3.390 (2)	134
C7—H7⋯O2ⁱ	0.95	2.68	3.543 (2)	152
Symmetry codes: (i) x, y+1, z; (ii) $[-x, -y, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 2004 ); 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 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050363/ds2011sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050363/ds2011Isup2.hkl

checkCIF report

Comment top

During our studies on the ambident reactivity of the phenylsulfinate anion we used diarylcarbenium ions (Ar₂CH⁺) as reference electrophiles [Mayr et al. (2001, 2008)] and, hence, obtained the title compound from a reaction of sodium benzenesulfinate with benzhydryl chloride (Ph₂CHCl) in dimethyl sulfoxide.

The asymmetric unit of the title compound contains one complete molecule, which is shown in Figure 1. The sulfur-bound phenyl group is approximately parallel to one of the two phenyl rings of the benzhydryl group with an dihedral angle of 12.53 (10)°. The other one forms a dihedral angle of 41.25 (9)° with the phenyl group bound to the sulfur atom.

Three weak C–H···O interactions are found (Table 1) which lead to the formation of a two-dimensional network that propagates along the bc plane (Fig. 2). Contacts of this type have been described for a structure of a related sulfone [Li et al. (2005)]. In terms of graph-set analysis [Bernstein et al. (1995), Etter et al. (1990)], the descriptors on the unitary level are C₁¹(4) for the H1···O2 interaction, C₁¹(6) for the H7···O2 interaction, and C₁¹(7) for the H4···O1 interaction.

Related literature top

For background to the sulfone anion, see: da Silva Corrêa et al. (1968); Mayr et al. (2001, 2008). For a related structure, see: Li et al. (2005). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental top

Benzhydryl Phenyl Sulfone was obtained by heating a mixture of sodium benzenesulfinate (0.21 g, 1.3 mmol) and benzhydryl chloride (0.26 g, 1.3 mmol) in DMSO at 70 °C. After completion of the reaction (4 h), the reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic phase was washed several times with water and dried (MgSO₄). A viscous oil was obtained after evaporation of the solvent under reduced pressure that solidified on standing. After column chromatography (silica gel, isohexane/EtOAc = 9/1), benzhydryl phenyl sulfone was isolated as colorless solid (0.33 g, 82%). A small amount of the title compound was dissolved in ethyl acetate. The solvent was allowed to evaporate slowly at room temperature. After 2 days crystals had formed that were suitable for X-ray analysis. mp 189 °C (186–187 °C [da Silva Corrêa et al. (1968)]).

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. Weak intermolecular hydrogen bonds of the type C–H···O leading to a two-dimensional network that propagates along the bc plane (viewing direction approximately along [110]). Color scheme for dashed lines: blue: H1···O2 contacts, red: H7···O2 contacts, green: H4···O1 contacts.

Benzhydryl phenyl sulfone top

Crystal data top

C₁₉H₁₆O₂S	F(000) = 648
M_r = 308.40	D_x = 1.312 (1) Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6504 reflections
a = 16.3250 (4) Å	θ = 3.1–27.5°
b = 5.7979 (1) Å	µ = 0.21 mm⁻¹
c = 16.4983 (4) Å	T = 200 K
V = 1561.58 (6) Å³	Rod, colourless
Z = 4	0.20 × 0.10 × 0.09 mm

Data collection top

Nonius KappaCCD diffractometer	3136 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.027
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 27.5°, θ_min = 3.5°
Detector resolution: 9 pixels mm^-1	h = −21→21
CCD; rotation images; thick slices, phi/ω–scan	k = −7→6
11675 measured reflections	l = −21→20
3499 independent reflections

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)] = 0.031	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0396P)² + 0.2163P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3499 reflections	Δρ_max = 0.14 e Å⁻³
199 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1646 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (6)

Crystal data top

C₁₉H₁₆O₂S	V = 1561.58 (6) Å³
M_r = 308.40	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 16.3250 (4) Å	µ = 0.21 mm⁻¹
b = 5.7979 (1) Å	T = 200 K
c = 16.4983 (4) Å	0.20 × 0.10 × 0.09 mm

Data collection top

Nonius KappaCCD diffractometer	3136 reflections with I > 2σ(I)
11675 measured reflections	R_int = 0.027
3499 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.075	Δρ_max = 0.14 e Å⁻³
S = 1.04	Δρ_min = −0.28 e Å⁻³
3499 reflections	Absolute structure: Flack (1983), 1646 Friedel pairs
199 parameters	Absolute structure parameter: −0.03 (6)
1 restraint

Special details top

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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.06340 (2)	0.12898 (6)	0.26302 (3)	0.02887 (10)
O1	0.08669 (8)	0.1945 (2)	0.34378 (7)	0.0408 (3)
O2	0.03981 (7)	−0.10715 (19)	0.24877 (8)	0.0384 (3)
C1	−0.01788 (10)	0.3229 (3)	0.23092 (10)	0.0276 (3)
H1	0.0034	0.4820	0.2409	0.033*
C2	−0.03155 (9)	0.3073 (3)	0.14009 (10)	0.0272 (3)
C3	−0.06491 (11)	0.1160 (3)	0.10143 (11)	0.0347 (4)
H3	−0.0816	−0.0139	0.1324	0.042*
C4	−0.07391 (11)	0.1141 (3)	0.01781 (12)	0.0405 (4)
H4	−0.0964	−0.0180	−0.0080	0.049*
C5	−0.05082 (12)	0.2999 (4)	−0.02807 (12)	0.0428 (4)
H5	−0.0576	0.2970	−0.0853	0.051*
C6	−0.01740 (12)	0.4927 (4)	0.00955 (13)	0.0451 (5)
H6	−0.0008	0.6218	−0.0218	0.054*
C7	−0.00847 (11)	0.4955 (3)	0.09276 (11)	0.0363 (4)
H7	0.0138	0.6283	0.1182	0.044*
C8	−0.09145 (10)	0.2969 (3)	0.28610 (9)	0.0304 (4)
C9	−0.14154 (12)	0.1021 (3)	0.28814 (12)	0.0431 (4)
H9	−0.1290	−0.0274	0.2551	0.052*
C10	−0.20970 (13)	0.0971 (4)	0.33832 (13)	0.0500 (5)
H10	−0.2444	−0.0343	0.3383	0.060*
C11	−0.22748 (13)	0.2805 (4)	0.38811 (13)	0.0531 (5)
H11	−0.2740	0.2751	0.4227	0.064*
C12	−0.17763 (14)	0.4719 (4)	0.38771 (14)	0.0547 (5)
H12	−0.1895	0.5985	0.4223	0.066*
C13	−0.10994 (12)	0.4802 (3)	0.33668 (11)	0.0406 (4)
H13	−0.0760	0.6133	0.3365	0.049*
C14	0.14411 (10)	0.2005 (3)	0.19613 (10)	0.0292 (3)
C15	0.18653 (11)	0.4044 (3)	0.20890 (12)	0.0407 (4)
H15	0.1739	0.5002	0.2539	0.049*
C16	0.24784 (12)	0.4662 (3)	0.15468 (14)	0.0479 (5)
H16	0.2775	0.6055	0.1623	0.057*
C17	0.26549 (12)	0.3259 (4)	0.09010 (13)	0.0503 (5)
H17	0.3075	0.3691	0.0532	0.060*
C18	0.22315 (13)	0.1231 (4)	0.07798 (14)	0.0517 (5)
H18	0.2364	0.0267	0.0333	0.062*
C19	0.16122 (12)	0.0598 (3)	0.13093 (12)	0.0403 (4)
H19	0.1311	−0.0782	0.1224	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03180 (18)	0.02898 (18)	0.02584 (18)	0.00027 (14)	−0.00044 (18)	0.00176 (17)
O1	0.0447 (7)	0.0530 (8)	0.0247 (6)	0.0025 (6)	−0.0042 (5)	0.0005 (5)
O2	0.0408 (6)	0.0273 (6)	0.0471 (9)	−0.0006 (4)	0.0029 (6)	0.0047 (5)
C1	0.0315 (8)	0.0251 (8)	0.0263 (8)	−0.0019 (6)	0.0000 (7)	−0.0014 (6)
C2	0.0257 (7)	0.0301 (8)	0.0258 (8)	0.0028 (6)	0.0008 (6)	0.0011 (6)
C3	0.0384 (9)	0.0357 (9)	0.0301 (9)	−0.0062 (7)	−0.0017 (7)	−0.0001 (7)
C4	0.0394 (9)	0.0507 (11)	0.0312 (10)	−0.0053 (8)	−0.0032 (8)	−0.0060 (8)
C5	0.0423 (10)	0.0597 (12)	0.0262 (9)	0.0046 (9)	−0.0005 (8)	0.0006 (8)
C6	0.0561 (13)	0.0471 (11)	0.0321 (9)	0.0014 (9)	0.0063 (9)	0.0098 (7)
C7	0.0440 (10)	0.0316 (9)	0.0334 (9)	−0.0002 (7)	0.0045 (7)	0.0013 (7)
C8	0.0327 (8)	0.0324 (8)	0.0261 (9)	0.0015 (6)	−0.0017 (6)	0.0028 (6)
C9	0.0433 (10)	0.0450 (11)	0.0410 (11)	−0.0093 (8)	0.0040 (8)	−0.0017 (8)
C10	0.0403 (10)	0.0638 (13)	0.0460 (12)	−0.0138 (9)	0.0040 (9)	0.0146 (10)
C11	0.0409 (10)	0.0738 (14)	0.0445 (12)	0.0098 (10)	0.0133 (9)	0.0159 (11)
C12	0.0575 (13)	0.0597 (13)	0.0470 (12)	0.0113 (10)	0.0174 (10)	−0.0022 (10)
C13	0.0465 (10)	0.0412 (10)	0.0340 (10)	0.0044 (8)	0.0048 (8)	−0.0049 (8)
C14	0.0270 (8)	0.0333 (8)	0.0273 (8)	0.0008 (6)	−0.0026 (7)	0.0016 (7)
C15	0.0384 (10)	0.0429 (10)	0.0409 (11)	−0.0064 (8)	−0.0044 (8)	−0.0039 (8)
C16	0.0340 (9)	0.0507 (11)	0.0589 (13)	−0.0111 (9)	−0.0065 (9)	0.0088 (10)
C17	0.0320 (9)	0.0683 (13)	0.0505 (12)	0.0027 (9)	0.0089 (9)	0.0144 (10)
C18	0.0466 (11)	0.0625 (13)	0.0459 (12)	0.0048 (9)	0.0128 (10)	−0.0074 (10)
C19	0.0402 (9)	0.0394 (9)	0.0414 (11)	0.0016 (8)	0.0045 (8)	−0.0056 (8)

Geometric parameters (Å, º) top

S1—O1	1.4366 (13)	C9—C10	1.387 (3)
S1—O2	1.4415 (12)	C9—H9	0.9500
S1—C14	1.7681 (17)	C10—C11	1.374 (3)
S1—C1	1.8180 (16)	C10—H10	0.9500
C1—C8	1.514 (2)	C11—C12	1.376 (3)
C1—C2	1.518 (2)	C11—H11	0.9500
C1—H1	1.0000	C12—C13	1.390 (3)
C2—C3	1.390 (2)	C12—H12	0.9500
C2—C7	1.394 (2)	C13—H13	0.9500
C3—C4	1.387 (3)	C14—C19	1.379 (2)
C3—H3	0.9500	C14—C15	1.386 (2)
C4—C5	1.369 (3)	C15—C16	1.389 (3)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.390 (3)	C16—C17	1.371 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.381 (3)	C17—C18	1.378 (3)
C6—H6	0.9500	C17—H17	0.9500
C7—H7	0.9500	C18—C19	1.386 (3)
C8—C13	1.385 (2)	C18—H18	0.9500
C8—C9	1.395 (3)	C19—H19	0.9500

O1—S1—O2	118.23 (7)	C10—C9—C8	120.08 (19)
O1—S1—C14	108.64 (8)	C10—C9—H9	120.0
O2—S1—C14	108.67 (8)	C8—C9—H9	120.0
O1—S1—C1	107.45 (8)	C11—C10—C9	120.67 (19)
O2—S1—C1	110.16 (7)	C11—C10—H10	119.7
C14—S1—C1	102.53 (8)	C9—C10—H10	119.7
C8—C1—C2	118.10 (14)	C10—C11—C12	119.74 (19)
C8—C1—S1	110.02 (11)	C10—C11—H11	120.1
C2—C1—S1	110.99 (11)	C12—C11—H11	120.1
C8—C1—H1	105.6	C11—C12—C13	120.05 (19)
C2—C1—H1	105.6	C11—C12—H12	120.0
S1—C1—H1	105.6	C13—C12—H12	120.0
C3—C2—C7	118.25 (15)	C8—C13—C12	120.79 (18)
C3—C2—C1	123.92 (15)	C8—C13—H13	119.6
C7—C2—C1	117.83 (14)	C12—C13—H13	119.6
C4—C3—C2	120.27 (16)	C19—C14—C15	121.46 (17)
C4—C3—H3	119.9	C19—C14—S1	119.94 (13)
C2—C3—H3	119.9	C15—C14—S1	118.53 (13)
C5—C4—C3	120.94 (18)	C14—C15—C16	118.82 (18)
C5—C4—H4	119.5	C14—C15—H15	120.6
C3—C4—H4	119.5	C16—C15—H15	120.6
C4—C5—C6	119.59 (18)	C17—C16—C15	119.91 (18)
C4—C5—H5	120.2	C17—C16—H16	120.0
C6—C5—H5	120.2	C15—C16—H16	120.0
C7—C6—C5	119.67 (18)	C16—C17—C18	120.89 (19)
C7—C6—H6	120.2	C16—C17—H17	119.6
C5—C6—H6	120.2	C18—C17—H17	119.6
C6—C7—C2	121.27 (17)	C17—C18—C19	120.03 (19)
C6—C7—H7	119.4	C17—C18—H18	120.0
C2—C7—H7	119.4	C19—C18—H18	120.0
C13—C8—C9	118.64 (17)	C14—C19—C18	118.88 (18)
C13—C8—C1	117.33 (15)	C14—C19—H19	120.6
C9—C8—C1	124.03 (15)	C18—C19—H19	120.6

O1—S1—C1—C8	−61.76 (13)	C13—C8—C9—C10	1.9 (3)
O2—S1—C1—C8	68.31 (13)	C1—C8—C9—C10	−177.35 (17)
C14—S1—C1—C8	−176.16 (11)	C8—C9—C10—C11	−1.8 (3)
O1—S1—C1—C2	165.65 (11)	C9—C10—C11—C12	0.6 (3)
O2—S1—C1—C2	−64.28 (13)	C10—C11—C12—C13	0.5 (3)
C14—S1—C1—C2	51.25 (12)	C9—C8—C13—C12	−0.9 (3)
C8—C1—C2—C3	−59.0 (2)	C1—C8—C13—C12	178.46 (18)
S1—C1—C2—C3	69.33 (18)	C11—C12—C13—C8	−0.3 (3)
C8—C1—C2—C7	121.61 (17)	O1—S1—C14—C19	144.32 (14)
S1—C1—C2—C7	−110.03 (15)	O2—S1—C14—C19	14.45 (16)
C7—C2—C3—C4	0.6 (3)	C1—S1—C14—C19	−102.16 (15)
C1—C2—C3—C4	−178.76 (17)	O1—S1—C14—C15	−38.52 (16)
C2—C3—C4—C5	−0.5 (3)	O2—S1—C14—C15	−168.39 (13)
C3—C4—C5—C6	0.4 (3)	C1—S1—C14—C15	75.01 (15)
C4—C5—C6—C7	−0.5 (3)	C19—C14—C15—C16	−0.3 (3)
C5—C6—C7—C2	0.7 (3)	S1—C14—C15—C16	−177.45 (15)
C3—C2—C7—C6	−0.7 (3)	C14—C15—C16—C17	−0.2 (3)
C1—C2—C7—C6	178.68 (17)	C15—C16—C17—C18	0.0 (3)
C2—C1—C8—C13	−120.05 (16)	C16—C17—C18—C19	0.7 (3)
S1—C1—C8—C13	111.14 (15)	C15—C14—C19—C18	1.0 (3)
C2—C1—C8—C9	59.2 (2)	S1—C14—C19—C18	178.09 (15)
S1—C1—C8—C9	−69.59 (19)	C17—C18—C19—C14	−1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	1.00	2.46	3.449 (2)	171
C4—H4···O1ⁱⁱ	0.95	2.66	3.390 (2)	134
C7—H7···O2ⁱ	0.95	2.68	3.543 (2)	152

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆O₂S
M_r	308.40
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	200
a, b, c (Å)	16.3250 (4), 5.7979 (1), 16.4983 (4)
V (Å³)	1561.58 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.10 × 0.09

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11675, 3499, 3136
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.075, 1.04
No. of reflections	3499
No. of parameters	199
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.28
Absolute structure	Flack (1983), 1646 Friedel pairs
Absolute structure parameter	−0.03 (6)

Computer programs: COLLECT (Hooft, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	1.00	2.46	3.449 (2)	171
C4—H4···O1ⁱⁱ	0.95	2.66	3.390 (2)	134
C7—H7···O2ⁱ	0.95	2.68	3.543 (2)	152

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

Acknowledgements

The authors thank Professor Peter Klüfers for generous allocation of diffractometer time.

References

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