5-Chloro-3-cyclo­pentyl­sulfonyl-2-methyl-1-benzofuran

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

doi:10.1107/S160053681103933X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2805

https://doi.org/10.1107/S160053681103933X

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5-Chloro-3-cyclopentylsulfonyl-2-methyl-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 14 September 2011; accepted 25 September 2011; online 30 September 2011)

In the title compound, C₁₄H₁₅ClO₃S, the cyclopenyl ring adopts an envelope conformation. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds into dual chains propagating in [100]. The dual chains arise from pairs of the same or different hydrogen bonds between adjacent molecules.

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 the crystal structures of related compounds, see: Seo et al. (2011a ,b ).

Experimental

Crystal data

C₁₄H₁₅ClO₃S
M_r = 298.77
Triclinic, $[P \overline 1]$
a = 7.4833 (8) Å
b = 8.7888 (9) Å
c = 10.9061 (10) Å
α = 66.919 (5)°
β = 82.848 (6)°
γ = 82.689 (6)°
V = 652.31 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 173 K
0.39 × 0.27 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.844, T_max = 0.905
11884 measured reflections
3252 independent reflections
2721 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.143
S = 1.05
3252 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.95	2.51	3.420 (2)	160
C12—H12A⋯O2ⁱⁱ	0.99	2.59	3.557 (2)	167
C13—H13B⋯O3ⁱⁱ	0.99	2.61	3.516 (3)	153
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x+1, y, z.

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 datablocks global, I. DOI: https://doi.org/10.1107/S160053681103933X/cv5153sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103933X/cv5153Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103933X/cv5153Isup3.cml

checkCIF report

Comment top

Recently, many compounds containing a benzofuran moiety have received much attention because of 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 benzofuran derivatives containing either 3-cyclopentylsulfinyl (Seo et al., 2011a) or 3-cyclopentylsulfonyl (Seo et al., 2011b) substituents, we report herein the crystal structure of the title compound (I).

In (I) (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.005 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring is in the envelope form. In the crystal structure (Fig. 2), weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into dual chains propagated in [100] (Fig. 2).

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 the crystal structures of related compounds, see: Seo et al. (2011a,b).

Experimental top

77% 3-Chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclopentylsulfanyl-2-methyl-1-benzofuran (320 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 70%, m.p. 412–413 K; R_f = 0.46 (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 the crystal structures of related compounds, see: Seo et al. (2011a,b).

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···O hydrogen bonds (dotted lines) in the crystal structure of the title compound [symmetry codes: (i) - x, - y + 2, - z + 1; (ii) x + 1, y, z; (iii) x - 1, y, z.] H atoms non-participating in hydrogen-bonding were omitted for clarity.

5-Chloro-3-cyclopentylsulfonyl-2-methyl-1-benzofuran top

Crystal data top

C₁₄H₁₅ClO₃S	Z = 2
M_r = 298.77	F(000) = 312
Triclinic, P1	D_x = 1.521 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4833 (8) Å	Cell parameters from 5081 reflections
b = 8.7888 (9) Å	θ = 2.5–28.2°
c = 10.9061 (10) Å	µ = 0.45 mm⁻¹
α = 66.919 (5)°	T = 173 K
β = 82.848 (6)°	Block, colourless
γ = 82.689 (6)°	0.39 × 0.27 × 0.22 mm
V = 652.31 (11) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3252 independent reflections
Radiation source: rotating anode	2721 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.046
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.844, T_max = 0.905	l = −14→14
11884 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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F²) = 0.143	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3252 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₁₄H₁₅ClO₃S	γ = 82.689 (6)°
M_r = 298.77	V = 652.31 (11) Å³
Triclinic, P1	Z = 2
a = 7.4833 (8) Å	Mo Kα radiation
b = 8.7888 (9) Å	µ = 0.45 mm⁻¹
c = 10.9061 (10) Å	T = 173 K
α = 66.919 (5)°	0.39 × 0.27 × 0.22 mm
β = 82.848 (6)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3252 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2721 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.905	R_int = 0.046
11884 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.05	Δρ_max = 0.44 e Å⁻³
3252 reflections	Δρ_min = −0.73 e Å⁻³
173 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	0.01806 (6)	0.70534 (5)	0.73025 (4)	0.02070 (15)
Cl1	0.22626 (7)	0.92775 (6)	0.13290 (4)	0.03364 (17)
O1	0.26706 (18)	0.34648 (14)	0.62681 (11)	0.0261 (3)
O2	−0.07756 (18)	0.60437 (16)	0.85224 (11)	0.0291 (3)
O3	−0.08387 (17)	0.83205 (15)	0.62857 (11)	0.0257 (3)
C1	0.1369 (2)	0.5756 (2)	0.65566 (15)	0.0210 (3)
C2	0.1864 (2)	0.6199 (2)	0.51383 (15)	0.0209 (3)
C3	0.1721 (2)	0.7648 (2)	0.39920 (15)	0.0225 (4)
H3	0.1194	0.8673	0.4030	0.027*
C4	0.2388 (3)	0.7506 (2)	0.28003 (16)	0.0243 (4)
C5	0.3159 (3)	0.6020 (2)	0.27022 (17)	0.0276 (4)
H5	0.3586	0.5994	0.1853	0.033*
C6	0.3301 (3)	0.4594 (2)	0.38371 (17)	0.0274 (4)
H6	0.3818	0.3568	0.3797	0.033*
C7	0.2654 (2)	0.4727 (2)	0.50369 (15)	0.0221 (4)
C8	0.1883 (2)	0.4117 (2)	0.71738 (16)	0.0245 (4)
C9	0.1791 (3)	0.2926 (2)	0.85921 (17)	0.0321 (4)
H9A	0.1229	0.3503	0.9169	0.048*
H9B	0.3015	0.2468	0.8848	0.048*
H9C	0.1068	0.2023	0.8693	0.048*
C10	0.1818 (2)	0.8010 (2)	0.77215 (15)	0.0232 (4)
H10	0.1163	0.8755	0.8158	0.028*
C11	0.3143 (3)	0.6800 (2)	0.86896 (17)	0.0295 (4)
H11A	0.2577	0.6388	0.9618	0.035*
H11B	0.3568	0.5842	0.8436	0.035*
C12	0.4688 (3)	0.7835 (3)	0.85509 (18)	0.0328 (4)
H12A	0.5859	0.7157	0.8595	0.039*
H12B	0.4556	0.8253	0.9281	0.039*
C13	0.4615 (3)	0.9290 (2)	0.71898 (19)	0.0327 (4)
H13A	0.4423	1.0361	0.7310	0.039*
H13B	0.5758	0.9276	0.6629	0.039*
C14	0.3028 (3)	0.9064 (2)	0.65330 (16)	0.0278 (4)
H14A	0.2385	1.0147	0.6028	0.033*
H14B	0.3446	0.8483	0.5920	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0169 (3)	0.0228 (2)	0.0204 (2)	0.00049 (18)	−0.00042 (16)	−0.00706 (17)
Cl1	0.0423 (3)	0.0320 (3)	0.0211 (2)	−0.0046 (2)	−0.00045 (19)	−0.00445 (19)
O1	0.0293 (8)	0.0185 (6)	0.0285 (6)	0.0010 (5)	−0.0056 (5)	−0.0068 (5)
O2	0.0240 (7)	0.0365 (7)	0.0233 (6)	−0.0060 (6)	0.0040 (5)	−0.0084 (5)
O3	0.0214 (7)	0.0259 (6)	0.0272 (6)	0.0044 (5)	−0.0051 (5)	−0.0082 (5)
C1	0.0198 (9)	0.0212 (8)	0.0210 (7)	−0.0016 (7)	−0.0013 (6)	−0.0070 (6)
C2	0.0180 (9)	0.0215 (8)	0.0235 (7)	−0.0010 (7)	−0.0017 (6)	−0.0092 (6)
C3	0.0212 (9)	0.0217 (8)	0.0238 (7)	−0.0002 (7)	−0.0019 (6)	−0.0085 (6)
C4	0.0233 (10)	0.0263 (8)	0.0218 (7)	−0.0041 (7)	−0.0018 (6)	−0.0071 (6)
C5	0.0243 (10)	0.0352 (10)	0.0276 (8)	−0.0022 (8)	−0.0002 (7)	−0.0175 (8)
C6	0.0263 (10)	0.0258 (8)	0.0350 (9)	0.0027 (8)	−0.0045 (7)	−0.0176 (7)
C7	0.0209 (9)	0.0193 (7)	0.0250 (7)	−0.0007 (7)	−0.0041 (6)	−0.0070 (6)
C8	0.0221 (10)	0.0233 (8)	0.0272 (8)	−0.0024 (7)	−0.0039 (7)	−0.0079 (7)
C9	0.0375 (12)	0.0222 (8)	0.0295 (8)	−0.0025 (8)	−0.0084 (8)	−0.0007 (7)
C10	0.0202 (9)	0.0247 (8)	0.0245 (7)	0.0015 (7)	−0.0009 (6)	−0.0105 (7)
C11	0.0276 (11)	0.0326 (9)	0.0252 (8)	−0.0018 (8)	−0.0059 (7)	−0.0068 (7)
C12	0.0241 (11)	0.0447 (11)	0.0293 (9)	−0.0041 (9)	−0.0041 (7)	−0.0129 (8)
C13	0.0289 (12)	0.0274 (9)	0.0411 (10)	−0.0038 (8)	−0.0058 (8)	−0.0109 (8)
C14	0.0267 (11)	0.0265 (8)	0.0266 (8)	−0.0038 (8)	−0.0033 (7)	−0.0054 (7)

Geometric parameters (Å, º) top

S1—O2	1.4382 (12)	C8—C9	1.488 (2)
S1—O3	1.4415 (11)	C9—H9A	0.9800
S1—C1	1.7441 (16)	C9—H9B	0.9800
S1—C10	1.7664 (18)	C9—H9C	0.9800
Cl1—C4	1.7463 (17)	C10—C14	1.529 (2)
O1—C8	1.365 (2)	C10—C11	1.530 (2)
O1—C7	1.3662 (18)	C10—H10	1.0000
C1—C8	1.356 (2)	C11—C12	1.517 (3)
C1—C2	1.450 (2)	C11—H11A	0.9900
C2—C7	1.392 (2)	C11—H11B	0.9900
C2—C3	1.395 (2)	C12—C13	1.535 (3)
C3—C4	1.380 (2)	C12—H12A	0.9900
C3—H3	0.9500	C12—H12B	0.9900
C4—C5	1.397 (3)	C13—C14	1.531 (3)
C5—C6	1.378 (2)	C13—H13A	0.9900
C5—H5	0.9500	C13—H13B	0.9900
C6—C7	1.381 (2)	C14—H14A	0.9900
C6—H6	0.9500	C14—H14B	0.9900

O2—S1—O3	118.65 (8)	C8—C9—H9C	109.5
O2—S1—C1	108.48 (8)	H9A—C9—H9C	109.5
O3—S1—C1	106.51 (7)	H9B—C9—H9C	109.5
O2—S1—C10	108.07 (8)	C14—C10—C11	104.30 (15)
O3—S1—C10	108.11 (8)	C14—C10—S1	114.73 (12)
C1—S1—C10	106.39 (8)	C11—C10—S1	114.46 (12)
C8—O1—C7	106.90 (12)	C14—C10—H10	107.7
C8—C1—C2	107.01 (14)	C11—C10—H10	107.7
C8—C1—S1	126.67 (12)	S1—C10—H10	107.7
C2—C1—S1	126.15 (12)	C12—C11—C10	103.74 (15)
C7—C2—C3	120.01 (14)	C12—C11—H11A	111.0
C7—C2—C1	104.43 (14)	C10—C11—H11A	111.0
C3—C2—C1	135.56 (15)	C12—C11—H11B	111.0
C4—C3—C2	116.08 (15)	C10—C11—H11B	111.0
C4—C3—H3	122.0	H11A—C11—H11B	109.0
C2—C3—H3	122.0	C11—C12—C13	107.18 (15)
C3—C4—C5	123.68 (16)	C11—C12—H12A	110.3
C3—C4—Cl1	118.36 (13)	C13—C12—H12A	110.3
C5—C4—Cl1	117.96 (13)	C11—C12—H12B	110.3
C6—C5—C4	120.02 (15)	C13—C12—H12B	110.3
C6—C5—H5	120.0	H12A—C12—H12B	108.5
C4—C5—H5	120.0	C14—C13—C12	106.39 (17)
C5—C6—C7	116.75 (15)	C14—C13—H13A	110.5
C5—C6—H6	121.6	C12—C13—H13A	110.5
C7—C6—H6	121.6	C14—C13—H13B	110.5
O1—C7—C6	125.78 (14)	C12—C13—H13B	110.5
O1—C7—C2	110.78 (13)	H13A—C13—H13B	108.6
C6—C7—C2	123.44 (15)	C10—C14—C13	103.38 (14)
C1—C8—O1	110.88 (14)	C10—C14—H14A	111.1
C1—C8—C9	134.00 (15)	C13—C14—H14A	111.1
O1—C8—C9	115.11 (14)	C10—C14—H14B	111.1
C8—C9—H9A	109.5	C13—C14—H14B	111.1
C8—C9—H9B	109.5	H14A—C14—H14B	109.1
H9A—C9—H9B	109.5

O2—S1—C1—C8	−22.22 (19)	C1—C2—C7—O1	−0.2 (2)
O3—S1—C1—C8	−151.00 (17)	C3—C2—C7—C6	−1.1 (3)
C10—S1—C1—C8	93.83 (18)	C1—C2—C7—C6	179.06 (17)
O2—S1—C1—C2	152.39 (16)	C2—C1—C8—O1	0.0 (2)
O3—S1—C1—C2	23.61 (18)	S1—C1—C8—O1	175.43 (13)
C10—S1—C1—C2	−91.55 (17)	C2—C1—C8—C9	179.0 (2)
C8—C1—C2—C7	0.1 (2)	S1—C1—C8—C9	−5.5 (3)
S1—C1—C2—C7	−175.35 (14)	C7—O1—C8—C1	−0.1 (2)
C8—C1—C2—C3	−179.7 (2)	C7—O1—C8—C9	−179.37 (15)
S1—C1—C2—C3	4.8 (3)	O2—S1—C10—C14	176.93 (11)
C7—C2—C3—C4	0.3 (3)	O3—S1—C10—C14	−53.47 (13)
C1—C2—C3—C4	−179.85 (19)	C1—S1—C10—C14	60.60 (13)
C2—C3—C4—C5	0.5 (3)	O2—S1—C10—C11	56.38 (14)
C2—C3—C4—Cl1	−179.62 (13)	O3—S1—C10—C11	−174.02 (12)
C3—C4—C5—C6	−0.6 (3)	C1—S1—C10—C11	−59.95 (13)
Cl1—C4—C5—C6	179.48 (15)	C14—C10—C11—C12	37.10 (17)
C4—C5—C6—C7	−0.1 (3)	S1—C10—C11—C12	163.27 (12)
C8—O1—C7—C6	−179.05 (19)	C10—C11—C12—C13	−22.06 (19)
C8—O1—C7—C2	0.2 (2)	C11—C12—C13—C14	−1.1 (2)
C5—C6—C7—O1	−179.91 (17)	C11—C10—C14—C13	−37.65 (17)
C5—C6—C7—C2	0.9 (3)	S1—C10—C14—C13	−163.66 (12)
C3—C2—C7—O1	179.66 (15)	C12—C13—C14—C10	23.73 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.51	3.420 (2)	160
C12—H12A···O2ⁱⁱ	0.99	2.59	3.557 (2)	167
C13—H13B···O3ⁱⁱ	0.99	2.61	3.516 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅ClO₃S
M_r	298.77
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.4833 (8), 8.7888 (9), 10.9061 (10)
α, β, γ (°)	66.919 (5), 82.848 (6), 82.689 (6)
V (Å³)	652.31 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.39 × 0.27 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.844, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	11884, 3252, 2721
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.143, 1.05
No. of reflections	3252
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.73

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

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.51	3.420 (2)	160.2
C12—H12A···O2ⁱⁱ	0.99	2.59	3.557 (2)	166.7
C13—H13B···O3ⁱⁱ	0.99	2.61	3.516 (3)	152.7

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

References

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