3-(3-Chloro­phenyl­sulfon­yl)-2,5-dimethyl-1-benzofuran

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811035720

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2578

https://doi.org/10.1107/S1600536811035720

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3-(3-Chlorophenylsulfonyl)-2,5-dimethyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 22 August 2011; accepted 2 September 2011; online 14 September 2011)

In the title molecule, C₁₆H₁₃ClO₃S, the 3-chlorophenyl ring makes a dihedral angle of 76.30 (5)° with the mean plane of the benzofuran fragment. In the crystal, pairs of intermolecular C—H⋯π interactions link the molecules into inversion dimers.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₆H₁₃ClO₃S
M_r = 320.77
Triclinic, $[P \overline 1]$
a = 8.1000 (4) Å
b = 8.8622 (5) Å
c = 10.6898 (6) Å
α = 84.023 (3)°
β = 81.514 (3)°
γ = 72.378 (3)°
V = 721.90 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 173 K
0.28 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.579, T_max = 0.746
13538 measured reflections
3622 independent reflections
2951 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.05
3622 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯Cgⁱ	0.98	2.73	3.663 (2)	159
Symmetry code: (i) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035720/qm2026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035720/qm2026Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035720/qm2026Isup3.cml

checkCIF report

Comment top

Recently, many compounds containing a benzofuran ring system have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 3-chlorophenyl ring and the mean plane of the benzofuran fragment is 76.30 (5)° . The crystal packing (Fig.2) is stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C9—H9C···Cgⁱ, Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (514 mg, 2.3 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,5-dimethyl-1-benzofuran (317 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 68%, m.p. 396–397 K; Rf = 0.75 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Structure description top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of 3-(4-chlorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x, - y, - z + 1.]

3-(3-Chlorophenylsulfonyl)-2,5-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₃ClO₃S	Z = 2
M_r = 320.77	F(000) = 332
Triclinic, P1	D_x = 1.476 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1000 (4) Å	Cell parameters from 5186 reflections
b = 8.8622 (5) Å	θ = 2.4–27.9°
c = 10.6898 (6) Å	µ = 0.42 mm⁻¹
α = 84.023 (3)°	T = 173 K
β = 81.514 (3)°	Block, colourless
γ = 72.378 (3)°	0.28 × 0.27 × 0.19 mm
V = 721.90 (7) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3622 independent reflections
Radiation source: rotating anode	2951 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.051
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.579, T_max = 0.746	l = −14→14
13538 measured reflections

Refinement top

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0497P)² + 0.243P] where P = (F_o² + 2F_c²)/3
3622 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₆H₁₃ClO₃S	γ = 72.378 (3)°
M_r = 320.77	V = 721.90 (7) Å³
Triclinic, P1	Z = 2
a = 8.1000 (4) Å	Mo Kα radiation
b = 8.8622 (5) Å	µ = 0.42 mm⁻¹
c = 10.6898 (6) Å	T = 173 K
α = 84.023 (3)°	0.28 × 0.27 × 0.19 mm
β = 81.514 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3622 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2951 reflections with I > 2σ(I)
T_min = 0.579, T_max = 0.746	R_int = 0.051
13538 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.05	Δρ_max = 0.39 e Å⁻³
3622 reflections	Δρ_min = −0.40 e Å⁻³
192 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.33167 (5)	0.43504 (5)	0.29715 (4)	0.02475 (13)
Cl1	−0.08568 (7)	0.78553 (6)	−0.04210 (5)	0.04248 (16)
O1	0.49244 (16)	−0.00637 (14)	0.20581 (12)	0.0310 (3)
O2	0.45023 (15)	0.49763 (14)	0.20924 (13)	0.0328 (3)
O3	0.31247 (17)	0.46293 (15)	0.42888 (12)	0.0324 (3)
C1	0.3859 (2)	0.23236 (19)	0.28520 (16)	0.0239 (3)
C2	0.3302 (2)	0.12036 (19)	0.37751 (16)	0.0242 (3)
C3	0.2342 (2)	0.1260 (2)	0.49708 (16)	0.0272 (4)
H3	0.1872	0.2233	0.5372	0.033*
C4	0.2087 (2)	−0.0133 (2)	0.55658 (17)	0.0298 (4)
C5	0.2811 (2)	−0.1561 (2)	0.49675 (19)	0.0342 (4)
H5	0.2626	−0.2505	0.5389	0.041*
C6	0.3782 (2)	−0.1647 (2)	0.3793 (2)	0.0341 (4)
H6	0.4273	−0.2621	0.3395	0.041*
C7	0.3998 (2)	−0.0244 (2)	0.32300 (17)	0.0274 (4)
C8	0.4815 (2)	0.1509 (2)	0.18512 (17)	0.0273 (4)
C9	0.1031 (3)	−0.0119 (3)	0.68477 (19)	0.0404 (5)
H9A	0.1140	0.0730	0.7319	0.061*
H9B	0.1462	−0.1143	0.7316	0.061*
H9C	−0.0198	0.0063	0.6744	0.061*
C10	0.5727 (2)	0.1939 (2)	0.06278 (18)	0.0367 (4)
H10A	0.5343	0.3093	0.0459	0.055*
H10B	0.5455	0.1426	−0.0052	0.055*
H10C	0.6989	0.1584	0.0665	0.055*
C11	0.1232 (2)	0.51080 (19)	0.24554 (15)	0.0241 (3)
C12	−0.0193 (2)	0.4771 (2)	0.31850 (17)	0.0287 (4)
H12	−0.0056	0.4149	0.3963	0.034*
C13	−0.1810 (2)	0.5353 (2)	0.27665 (18)	0.0326 (4)
H13	−0.2789	0.5109	0.3250	0.039*
C14	−0.2017 (2)	0.6286 (2)	0.16502 (17)	0.0313 (4)
H14	−0.3133	0.6683	0.1362	0.038*
C15	−0.0585 (2)	0.6636 (2)	0.09564 (17)	0.0290 (4)
C16	0.1054 (2)	0.6038 (2)	0.13328 (16)	0.0277 (4)
H16	0.2037	0.6259	0.0835	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0225 (2)	0.0215 (2)	0.0316 (2)	−0.00858 (15)	−0.00493 (16)	0.00078 (16)
Cl1	0.0428 (3)	0.0451 (3)	0.0349 (3)	−0.0092 (2)	−0.0093 (2)	0.0141 (2)
O1	0.0274 (6)	0.0253 (6)	0.0376 (7)	−0.0053 (5)	0.0013 (5)	−0.0050 (5)
O2	0.0245 (6)	0.0294 (7)	0.0460 (8)	−0.0130 (5)	−0.0032 (5)	0.0051 (5)
O3	0.0383 (7)	0.0286 (6)	0.0335 (7)	−0.0114 (5)	−0.0106 (5)	−0.0027 (5)
C1	0.0210 (7)	0.0221 (7)	0.0294 (8)	−0.0071 (6)	−0.0048 (6)	0.0008 (6)
C2	0.0198 (7)	0.0225 (8)	0.0315 (9)	−0.0071 (6)	−0.0072 (6)	0.0010 (6)
C3	0.0259 (8)	0.0260 (8)	0.0300 (9)	−0.0075 (6)	−0.0059 (7)	0.0003 (7)
C4	0.0257 (8)	0.0330 (9)	0.0325 (9)	−0.0115 (7)	−0.0093 (7)	0.0067 (7)
C5	0.0314 (9)	0.0254 (9)	0.0469 (11)	−0.0114 (7)	−0.0093 (8)	0.0083 (8)
C6	0.0310 (9)	0.0222 (8)	0.0495 (12)	−0.0075 (7)	−0.0062 (8)	−0.0024 (8)
C7	0.0219 (8)	0.0256 (8)	0.0343 (9)	−0.0062 (6)	−0.0040 (7)	−0.0008 (7)
C8	0.0218 (8)	0.0256 (8)	0.0339 (9)	−0.0059 (6)	−0.0053 (7)	0.0001 (7)
C9	0.0420 (11)	0.0465 (11)	0.0343 (10)	−0.0199 (9)	−0.0036 (8)	0.0096 (9)
C10	0.0323 (9)	0.0402 (10)	0.0331 (10)	−0.0079 (8)	0.0025 (8)	0.0003 (8)
C11	0.0222 (8)	0.0223 (8)	0.0273 (8)	−0.0061 (6)	−0.0024 (6)	−0.0010 (6)
C12	0.0264 (8)	0.0293 (9)	0.0288 (9)	−0.0083 (7)	−0.0019 (7)	0.0047 (7)
C13	0.0237 (8)	0.0375 (10)	0.0349 (10)	−0.0095 (7)	0.0001 (7)	0.0023 (8)
C14	0.0241 (8)	0.0338 (9)	0.0330 (9)	−0.0034 (7)	−0.0054 (7)	−0.0011 (7)
C15	0.0307 (9)	0.0263 (8)	0.0270 (9)	−0.0046 (7)	−0.0045 (7)	0.0016 (7)
C16	0.0264 (8)	0.0257 (8)	0.0298 (9)	−0.0079 (7)	−0.0008 (7)	0.0012 (7)

Geometric parameters (Å, º) top

S1—O3	1.4328 (13)	C6—H6	0.9500
S1—O2	1.4355 (12)	C8—C10	1.478 (2)
S1—C1	1.7289 (17)	C9—H9A	0.9800
S1—C11	1.7659 (17)	C9—H9B	0.9800
Cl1—C15	1.7334 (18)	C9—H9C	0.9800
O1—C8	1.366 (2)	C10—H10A	0.9800
O1—C7	1.383 (2)	C10—H10B	0.9800
C1—C8	1.357 (2)	C10—H10C	0.9800
C1—C2	1.449 (2)	C11—C16	1.383 (2)
C2—C7	1.387 (2)	C11—C12	1.387 (2)
C2—C3	1.392 (2)	C12—C13	1.377 (3)
C3—C4	1.386 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.380 (3)
C4—C5	1.401 (3)	C13—H13	0.9500
C4—C9	1.504 (3)	C14—C15	1.381 (2)
C5—C6	1.376 (3)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.376 (2)
C6—C7	1.373 (3)	C16—H16	0.9500

O3—S1—O2	119.46 (8)	C4—C9—H9A	109.5
O3—S1—C1	107.56 (8)	C4—C9—H9B	109.5
O2—S1—C1	109.13 (8)	H9A—C9—H9B	109.5
O3—S1—C11	107.49 (8)	C4—C9—H9C	109.5
O2—S1—C11	107.47 (8)	H9A—C9—H9C	109.5
C1—S1—C11	104.80 (8)	H9B—C9—H9C	109.5
C8—O1—C7	106.97 (13)	C8—C10—H10A	109.5
C8—C1—C2	107.83 (15)	C8—C10—H10B	109.5
C8—C1—S1	126.08 (13)	H10A—C10—H10B	109.5
C2—C1—S1	126.02 (12)	C8—C10—H10C	109.5
C7—C2—C3	119.05 (16)	H10A—C10—H10C	109.5
C7—C2—C1	104.37 (15)	H10B—C10—H10C	109.5
C3—C2—C1	136.58 (16)	C16—C11—C12	121.36 (16)
C4—C3—C2	118.71 (16)	C16—C11—S1	119.09 (12)
C4—C3—H3	120.6	C12—C11—S1	119.55 (13)
C2—C3—H3	120.6	C13—C12—C11	119.07 (16)
C3—C4—C5	119.84 (16)	C13—C12—H12	120.5
C3—C4—C9	120.42 (17)	C11—C12—H12	120.5
C5—C4—C9	119.74 (17)	C12—C13—C14	120.52 (16)
C6—C5—C4	122.43 (17)	C12—C13—H13	119.7
C6—C5—H5	118.8	C14—C13—H13	119.7
C4—C5—H5	118.8	C13—C14—C15	119.29 (17)
C7—C6—C5	116.06 (17)	C13—C14—H14	120.4
C7—C6—H6	122.0	C15—C14—H14	120.4
C5—C6—H6	122.0	C16—C15—C14	121.53 (16)
C6—C7—O1	125.54 (16)	C16—C15—Cl1	119.16 (14)
C6—C7—C2	123.90 (16)	C14—C15—Cl1	119.31 (14)
O1—C7—C2	110.56 (15)	C15—C16—C11	118.19 (16)
C1—C8—O1	110.26 (15)	C15—C16—H16	120.9
C1—C8—C10	134.82 (17)	C11—C16—H16	120.9
O1—C8—C10	114.92 (15)

O3—S1—C1—C8	−151.41 (16)	C1—C2—C7—O1	0.08 (19)
O2—S1—C1—C8	−20.43 (19)	C2—C1—C8—O1	−0.2 (2)
C11—S1—C1—C8	94.41 (17)	S1—C1—C8—O1	−177.39 (12)
O3—S1—C1—C2	31.89 (17)	C2—C1—C8—C10	179.7 (2)
O2—S1—C1—C2	162.86 (14)	S1—C1—C8—C10	2.5 (3)
C11—S1—C1—C2	−82.29 (16)	C7—O1—C8—C1	0.2 (2)
C8—C1—C2—C7	0.06 (19)	C7—O1—C8—C10	−179.65 (15)
S1—C1—C2—C7	177.27 (13)	O3—S1—C11—C16	133.45 (14)
C8—C1—C2—C3	179.0 (2)	O2—S1—C11—C16	3.68 (16)
S1—C1—C2—C3	−3.8 (3)	C1—S1—C11—C16	−112.32 (14)
C7—C2—C3—C4	−1.3 (3)	O3—S1—C11—C12	−46.03 (16)
C1—C2—C3—C4	179.93 (18)	O2—S1—C11—C12	−175.80 (14)
C2—C3—C4—C5	0.9 (3)	C1—S1—C11—C12	68.19 (16)
C2—C3—C4—C9	−178.90 (17)	C16—C11—C12—C13	1.3 (3)
C3—C4—C5—C6	−0.1 (3)	S1—C11—C12—C13	−179.25 (14)
C9—C4—C5—C6	179.68 (18)	C11—C12—C13—C14	−1.4 (3)
C4—C5—C6—C7	−0.3 (3)	C12—C13—C14—C15	−0.2 (3)
C5—C6—C7—O1	179.85 (17)	C13—C14—C15—C16	1.9 (3)
C5—C6—C7—C2	−0.1 (3)	C13—C14—C15—Cl1	−178.12 (15)
C8—O1—C7—C6	179.81 (18)	C14—C15—C16—C11	−2.0 (3)
C8—O1—C7—C2	−0.20 (19)	Cl1—C15—C16—C11	178.02 (13)
C3—C2—C7—C6	0.9 (3)	C12—C11—C16—C15	0.4 (3)
C1—C2—C7—C6	−179.93 (17)	S1—C11—C16—C15	−179.09 (13)
C3—C2—C7—O1	−179.07 (15)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cgⁱ	0.98	2.73	3.663 (2)	159

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClO₃S
M_r	320.77
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.1000 (4), 8.8622 (5), 10.6898 (6)
α, β, γ (°)	84.023 (3), 81.514 (3), 72.378 (3)
V (Å³)	721.90 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.28 × 0.27 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.579, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13538, 3622, 2951
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.05
No. of reflections	3622
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···Cgⁱ	0.98	2.73	3.663 (2)	159.1

Symmetry code: (i) −x, −y, −z+1.

References

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