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ISSN: 2056-9890

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

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[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For the crystal structures of related compounds, see: Seo et al. (2011a[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o1386.],b[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o1689.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15ClO3S

  • Mr = 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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.844, Tmax = 0.905

  • 11884 measured reflections

  • 3252 independent reflections

  • 2721 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.143

  • S = 1.05

  • 3252 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.73 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


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; Rf = 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.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) =1.2Ueq(C) for aryl, methine and methylene, and 1.5Ueq(C) for methyl H atoms.

Structure description 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).

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
[Figure 1] 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.
[Figure 2] 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
C14H15ClO3SZ = 2
Mr = 298.77F(000) = 312
Triclinic, P1Dx = 1.521 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4833 (8) ÅCell parameters from 5081 reflections
b = 8.7888 (9) Åθ = 2.5–28.2°
c = 10.9061 (10) ŵ = 0.45 mm1
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 anode2721 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.046
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.0°
φ and ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1111
Tmin = 0.844, Tmax = 0.905l = 1414
11884 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.143H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
3252 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.73 e Å3
Crystal data top
C14H15ClO3Sγ = 82.689 (6)°
Mr = 298.77V = 652.31 (11) Å3
Triclinic, P1Z = 2
a = 7.4833 (8) ÅMo Kα radiation
b = 8.7888 (9) ŵ = 0.45 mm1
c = 10.9061 (10) ÅT = 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)
Tmin = 0.844, Tmax = 0.905Rint = 0.046
11884 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.05Δρmax = 0.44 e Å3
3252 reflectionsΔρmin = 0.73 e Å3
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
xyzUiso*/Ueq
S10.01806 (6)0.70534 (5)0.73025 (4)0.02070 (15)
Cl10.22626 (7)0.92775 (6)0.13290 (4)0.03364 (17)
O10.26706 (18)0.34648 (14)0.62681 (11)0.0261 (3)
O20.07756 (18)0.60437 (16)0.85224 (11)0.0291 (3)
O30.08387 (17)0.83205 (15)0.62857 (11)0.0257 (3)
C10.1369 (2)0.5756 (2)0.65566 (15)0.0210 (3)
C20.1864 (2)0.6199 (2)0.51383 (15)0.0209 (3)
C30.1721 (2)0.7648 (2)0.39920 (15)0.0225 (4)
H30.11940.86730.40300.027*
C40.2388 (3)0.7506 (2)0.28003 (16)0.0243 (4)
C50.3159 (3)0.6020 (2)0.27022 (17)0.0276 (4)
H50.35860.59940.18530.033*
C60.3301 (3)0.4594 (2)0.38371 (17)0.0274 (4)
H60.38180.35680.37970.033*
C70.2654 (2)0.4727 (2)0.50369 (15)0.0221 (4)
C80.1883 (2)0.4117 (2)0.71738 (16)0.0245 (4)
C90.1791 (3)0.2926 (2)0.85921 (17)0.0321 (4)
H9A0.12290.35030.91690.048*
H9B0.30150.24680.88480.048*
H9C0.10680.20230.86930.048*
C100.1818 (2)0.8010 (2)0.77215 (15)0.0232 (4)
H100.11630.87550.81580.028*
C110.3143 (3)0.6800 (2)0.86896 (17)0.0295 (4)
H11A0.25770.63880.96180.035*
H11B0.35680.58420.84360.035*
C120.4688 (3)0.7835 (3)0.85509 (18)0.0328 (4)
H12A0.58590.71570.85950.039*
H12B0.45560.82530.92810.039*
C130.4615 (3)0.9290 (2)0.71898 (19)0.0327 (4)
H13A0.44231.03610.73100.039*
H13B0.57580.92760.66290.039*
C140.3028 (3)0.9064 (2)0.65330 (16)0.0278 (4)
H14A0.23851.01470.60280.033*
H14B0.34460.84830.59200.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0169 (3)0.0228 (2)0.0204 (2)0.00049 (18)0.00042 (16)0.00706 (17)
Cl10.0423 (3)0.0320 (3)0.0211 (2)0.0046 (2)0.00045 (19)0.00445 (19)
O10.0293 (8)0.0185 (6)0.0285 (6)0.0010 (5)0.0056 (5)0.0068 (5)
O20.0240 (7)0.0365 (7)0.0233 (6)0.0060 (6)0.0040 (5)0.0084 (5)
O30.0214 (7)0.0259 (6)0.0272 (6)0.0044 (5)0.0051 (5)0.0082 (5)
C10.0198 (9)0.0212 (8)0.0210 (7)0.0016 (7)0.0013 (6)0.0070 (6)
C20.0180 (9)0.0215 (8)0.0235 (7)0.0010 (7)0.0017 (6)0.0092 (6)
C30.0212 (9)0.0217 (8)0.0238 (7)0.0002 (7)0.0019 (6)0.0085 (6)
C40.0233 (10)0.0263 (8)0.0218 (7)0.0041 (7)0.0018 (6)0.0071 (6)
C50.0243 (10)0.0352 (10)0.0276 (8)0.0022 (8)0.0002 (7)0.0175 (8)
C60.0263 (10)0.0258 (8)0.0350 (9)0.0027 (8)0.0045 (7)0.0176 (7)
C70.0209 (9)0.0193 (7)0.0250 (7)0.0007 (7)0.0041 (6)0.0070 (6)
C80.0221 (10)0.0233 (8)0.0272 (8)0.0024 (7)0.0039 (7)0.0079 (7)
C90.0375 (12)0.0222 (8)0.0295 (8)0.0025 (8)0.0084 (8)0.0007 (7)
C100.0202 (9)0.0247 (8)0.0245 (7)0.0015 (7)0.0009 (6)0.0105 (7)
C110.0276 (11)0.0326 (9)0.0252 (8)0.0018 (8)0.0059 (7)0.0068 (7)
C120.0241 (11)0.0447 (11)0.0293 (9)0.0041 (9)0.0041 (7)0.0129 (8)
C130.0289 (12)0.0274 (9)0.0411 (10)0.0038 (8)0.0058 (8)0.0109 (8)
C140.0267 (11)0.0265 (8)0.0266 (8)0.0038 (8)0.0033 (7)0.0054 (7)
Geometric parameters (Å, º) top
S1—O21.4382 (12)C8—C91.488 (2)
S1—O31.4415 (11)C9—H9A0.9800
S1—C11.7441 (16)C9—H9B0.9800
S1—C101.7664 (18)C9—H9C0.9800
Cl1—C41.7463 (17)C10—C141.529 (2)
O1—C81.365 (2)C10—C111.530 (2)
O1—C71.3662 (18)C10—H101.0000
C1—C81.356 (2)C11—C121.517 (3)
C1—C21.450 (2)C11—H11A0.9900
C2—C71.392 (2)C11—H11B0.9900
C2—C31.395 (2)C12—C131.535 (3)
C3—C41.380 (2)C12—H12A0.9900
C3—H30.9500C12—H12B0.9900
C4—C51.397 (3)C13—C141.531 (3)
C5—C61.378 (2)C13—H13A0.9900
C5—H50.9500C13—H13B0.9900
C6—C71.381 (2)C14—H14A0.9900
C6—H60.9500C14—H14B0.9900
O2—S1—O3118.65 (8)C8—C9—H9C109.5
O2—S1—C1108.48 (8)H9A—C9—H9C109.5
O3—S1—C1106.51 (7)H9B—C9—H9C109.5
O2—S1—C10108.07 (8)C14—C10—C11104.30 (15)
O3—S1—C10108.11 (8)C14—C10—S1114.73 (12)
C1—S1—C10106.39 (8)C11—C10—S1114.46 (12)
C8—O1—C7106.90 (12)C14—C10—H10107.7
C8—C1—C2107.01 (14)C11—C10—H10107.7
C8—C1—S1126.67 (12)S1—C10—H10107.7
C2—C1—S1126.15 (12)C12—C11—C10103.74 (15)
C7—C2—C3120.01 (14)C12—C11—H11A111.0
C7—C2—C1104.43 (14)C10—C11—H11A111.0
C3—C2—C1135.56 (15)C12—C11—H11B111.0
C4—C3—C2116.08 (15)C10—C11—H11B111.0
C4—C3—H3122.0H11A—C11—H11B109.0
C2—C3—H3122.0C11—C12—C13107.18 (15)
C3—C4—C5123.68 (16)C11—C12—H12A110.3
C3—C4—Cl1118.36 (13)C13—C12—H12A110.3
C5—C4—Cl1117.96 (13)C11—C12—H12B110.3
C6—C5—C4120.02 (15)C13—C12—H12B110.3
C6—C5—H5120.0H12A—C12—H12B108.5
C4—C5—H5120.0C14—C13—C12106.39 (17)
C5—C6—C7116.75 (15)C14—C13—H13A110.5
C5—C6—H6121.6C12—C13—H13A110.5
C7—C6—H6121.6C14—C13—H13B110.5
O1—C7—C6125.78 (14)C12—C13—H13B110.5
O1—C7—C2110.78 (13)H13A—C13—H13B108.6
C6—C7—C2123.44 (15)C10—C14—C13103.38 (14)
C1—C8—O1110.88 (14)C10—C14—H14A111.1
C1—C8—C9134.00 (15)C13—C14—H14A111.1
O1—C8—C9115.11 (14)C10—C14—H14B111.1
C8—C9—H9A109.5C13—C14—H14B111.1
C8—C9—H9B109.5H14A—C14—H14B109.1
H9A—C9—H9B109.5
O2—S1—C1—C822.22 (19)C1—C2—C7—O10.2 (2)
O3—S1—C1—C8151.00 (17)C3—C2—C7—C61.1 (3)
C10—S1—C1—C893.83 (18)C1—C2—C7—C6179.06 (17)
O2—S1—C1—C2152.39 (16)C2—C1—C8—O10.0 (2)
O3—S1—C1—C223.61 (18)S1—C1—C8—O1175.43 (13)
C10—S1—C1—C291.55 (17)C2—C1—C8—C9179.0 (2)
C8—C1—C2—C70.1 (2)S1—C1—C8—C95.5 (3)
S1—C1—C2—C7175.35 (14)C7—O1—C8—C10.1 (2)
C8—C1—C2—C3179.7 (2)C7—O1—C8—C9179.37 (15)
S1—C1—C2—C34.8 (3)O2—S1—C10—C14176.93 (11)
C7—C2—C3—C40.3 (3)O3—S1—C10—C1453.47 (13)
C1—C2—C3—C4179.85 (19)C1—S1—C10—C1460.60 (13)
C2—C3—C4—C50.5 (3)O2—S1—C10—C1156.38 (14)
C2—C3—C4—Cl1179.62 (13)O3—S1—C10—C11174.02 (12)
C3—C4—C5—C60.6 (3)C1—S1—C10—C1159.95 (13)
Cl1—C4—C5—C6179.48 (15)C14—C10—C11—C1237.10 (17)
C4—C5—C6—C70.1 (3)S1—C10—C11—C12163.27 (12)
C8—O1—C7—C6179.05 (19)C10—C11—C12—C1322.06 (19)
C8—O1—C7—C20.2 (2)C11—C12—C13—C141.1 (2)
C5—C6—C7—O1179.91 (17)C11—C10—C14—C1337.65 (17)
C5—C6—C7—C20.9 (3)S1—C10—C14—C13163.66 (12)
C3—C2—C7—O1179.66 (15)C12—C13—C14—C1023.73 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O3i0.952.513.420 (2)160
C12—H12A···O2ii0.992.593.557 (2)167
C13—H13B···O3ii0.992.613.516 (3)153
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H15ClO3S
Mr298.77
Crystal system, space groupTriclinic, 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)
V3)652.31 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.45
Crystal size (mm)0.39 × 0.27 × 0.22
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.844, 0.905
No. of measured, independent and
observed [I > 2σ(I)] reflections
11884, 3252, 2721
Rint0.046
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.143, 1.05
No. of reflections3252
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C3—H3···O3i0.952.513.420 (2)160.2
C12—H12A···O2ii0.992.593.557 (2)166.7
C13—H13B···O3ii0.992.613.516 (3)152.7
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y, z.
 

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