organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Crystal structure of benzobi­cyclon

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 52828, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

Edited by J. Simpson, University of Otago, New Zealand (Received 27 November 2015; accepted 2 December 2015; online 9 December 2015)

In the title compound, C22H19ClO4S2 [systematic name: 3-(2-chloro-4-mesylbenzo­yl)-4-(phenyl­sulfan­yl)bi­cyclo­[3.2.1]oct-3-en-2-one], which is an unclassified herbicide, the dihedral angle between the plane of the phenyl and chloro­benzene rings is 19.9 (2)°. In the crystal, C—H⋯O hydrogen bonds link adjacent mol­ecules, generating two-dimensional networks extending parellel to (011).

1. Related literature

For information on the herbicidal properties of the title compound, see: Im et al. (2015[Im, S. J., Abd El-Aty, A. M., Lee, Y.-J., Rahman, M. M., Kim, S.-W., Choi, J.-H. & Shim, J.-H. (2015). Food Chem. 168, 404-409.]). For related crystal structures, see: Brown et al. (2007[Brown, P. M., Käppel, N., Murphy, P. J., Coles, S. J. & Hursthouse, M. B. (2007). Tetrahedron, 63, 1100-1106.]); Hou et al. (2010[Hou, Y.-J., Chu, W.-Y., Sui, J. & Sun, Z.-Z. (2010). Z. Kristallogr. 225, 465-466.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C22H19ClO4S2

  • Mr = 446.94

  • Monoclinic, P 21 /c

  • a = 15.5111 (8) Å

  • b = 10.7218 (6) Å

  • c = 12.0169 (6) Å

  • β = 91.449 (3)°

  • V = 1997.85 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 173 K

  • 0.15 × 0.11 × 0.06 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.687, Tmax = 0.746

  • 15850 measured reflections

  • 3504 independent reflections

  • 2584 reflections with I > 2σ(I)

  • Rint = 0.055

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.142

  • S = 1.07

  • 3504 reflections

  • 263 parameters

  • H-atom parameters constrained

  • Δρmax = 0.97 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1B⋯O4i 0.98 2.44 3.322 (4) 150
C1—H1C⋯O4ii 0.98 2.52 3.477 (5) 165
C3—H3⋯O2iii 0.95 2.53 3.422 (4) 157
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. 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: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Benzobicyclon is a newly developed compound with potent herbicidal activity against Scirpus juncoides, one of the most troublesome weeds in paddy fields. (Im et al., 2015). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angle between the plane of the phenyl and chlorobenzene rings is 19.9 (2)°. All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of similar compounds (Brown et al., 2007; Hou et al., 2010).

In the crystal structure (Fig. 2), intermolecular C1—H1B···O4 hydrogen bond link adjacent molecules, forming chains along the c-axis direction. These chains are linked by C1—H1C···O4 and C3—H3···O2 hydrogen bonds (Table 1), resulting in two-dimensional networks extending parellel to the (011) plane.

Related literature top

For information on the herbicidal properties of the title compound, see: Im et al. (2015). For related crystal structures, see: Brown et al. (2007); Hou et al. (2010).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2C12 gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 1.00 Å, Uiso = 1.2Ueq(C) for Csp3—H, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 groups, d(C—H) = 0.98 Å, Uiso = 1.2Ueq(C) for CH3 groups, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.

Structure description top

Benzobicyclon is a newly developed compound with potent herbicidal activity against Scirpus juncoides, one of the most troublesome weeds in paddy fields. (Im et al., 2015). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angle between the plane of the phenyl and chlorobenzene rings is 19.9 (2)°. All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of similar compounds (Brown et al., 2007; Hou et al., 2010).

In the crystal structure (Fig. 2), intermolecular C1—H1B···O4 hydrogen bond link adjacent molecules, forming chains along the c-axis direction. These chains are linked by C1—H1C···O4 and C3—H3···O2 hydrogen bonds (Table 1), resulting in two-dimensional networks extending parellel to the (011) plane.

For information on the herbicidal properties of the title compound, see: Im et al. (2015). For related crystal structures, see: Brown et al. (2007); Hou et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing viewed along the c axis. The intermolecular hydrogen bonds are shown as dashed lines.
3-(2-Chloro-4-mesylbenzoyl)-4-(phenylsulfanyl)bicyclo[3.2.1]oct-3-en-2-one top
Crystal data top
C22H19ClO4S2F(000) = 928
Mr = 446.94Dx = 1.486 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.5111 (8) ÅCell parameters from 2645 reflections
b = 10.7218 (6) Åθ = 2.6–24.7°
c = 12.0169 (6) ŵ = 0.43 mm1
β = 91.449 (3)°T = 173 K
V = 1997.85 (18) Å3Block, colourless
Z = 40.15 × 0.11 × 0.06 mm
Data collection top
Bruker APEXII CCD
diffractometer
2584 reflections with I > 2σ(I)
φ and ω scansRint = 0.055
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 25.0°, θmin = 2.3°
Tmin = 0.687, Tmax = 0.746h = 1818
15850 measured reflectionsk = 1112
3504 independent reflectionsl = 1412
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0619P)2 + 2.0045P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3504 reflectionsΔρmax = 0.97 e Å3
263 parametersΔρmin = 0.54 e Å3
Crystal data top
C22H19ClO4S2V = 1997.85 (18) Å3
Mr = 446.94Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.5111 (8) ŵ = 0.43 mm1
b = 10.7218 (6) ÅT = 173 K
c = 12.0169 (6) Å0.15 × 0.11 × 0.06 mm
β = 91.449 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
3504 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
2584 reflections with I > 2σ(I)
Tmin = 0.687, Tmax = 0.746Rint = 0.055
15850 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.07Δρmax = 0.97 e Å3
3504 reflectionsΔρmin = 0.54 e Å3
263 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.22882 (6)0.40049 (9)0.83242 (9)0.0464 (3)
S10.08667 (6)0.26508 (9)0.95779 (9)0.0361 (3)
S20.41445 (6)0.12501 (8)0.64532 (8)0.0324 (3)
O10.16416 (16)0.2346 (3)0.8963 (2)0.0495 (8)
O20.07793 (17)0.3867 (2)1.0065 (3)0.0499 (8)
O30.24478 (16)0.0592 (2)0.6713 (2)0.0429 (7)
O40.14394 (16)0.3801 (3)0.5647 (3)0.0479 (8)
C10.0691 (2)0.1524 (4)1.0616 (3)0.0401 (10)
H1A0.10830.16741.12280.060*
H1B0.00930.15761.08950.060*
H1C0.07990.06921.03040.060*
C20.0015 (2)0.2413 (3)0.8691 (3)0.0303 (8)
C30.0716 (2)0.3211 (3)0.8792 (3)0.0339 (9)
H30.07150.38840.93050.041*
C40.1417 (2)0.3002 (3)0.8126 (3)0.0309 (8)
C50.1442 (2)0.2011 (3)0.7389 (3)0.0290 (8)
C60.0730 (2)0.1218 (3)0.7314 (3)0.0335 (9)
H60.07360.05300.68160.040*
C70.0013 (2)0.1420 (3)0.7954 (3)0.0338 (9)
H70.04730.08830.78900.041*
C80.2214 (2)0.1671 (3)0.6715 (3)0.0302 (8)
C90.2696 (2)0.2642 (3)0.6103 (3)0.0336 (9)
C100.3565 (2)0.2546 (3)0.5982 (3)0.0310 (8)
C110.4045 (2)0.3595 (4)0.5419 (3)0.0382 (9)
H110.46560.33610.52740.046*
C120.3542 (4)0.3935 (5)0.4330 (3)0.0668 (16)
H12A0.33470.31910.39060.080*
H12B0.38700.44990.38450.080*
C130.2767 (3)0.4631 (4)0.4939 (5)0.0711 (17)
H130.24070.51440.44110.085*
C140.3207 (4)0.5376 (5)0.5754 (5)0.0755 (17)
H14A0.28380.54990.64050.091*
H14B0.33410.62040.54380.091*
C150.3992 (3)0.4753 (4)0.6092 (4)0.0622 (14)
H15A0.39830.45480.68950.075*
H15B0.44950.52950.59580.075*
C160.2224 (2)0.3702 (4)0.5594 (4)0.0466 (11)
C170.5234 (2)0.1795 (3)0.6555 (3)0.0299 (8)
C180.5496 (3)0.2579 (3)0.7411 (3)0.0404 (10)
H180.50850.28920.79140.048*
C190.6355 (3)0.2910 (4)0.7538 (4)0.0532 (12)
H190.65360.34600.81180.064*
C200.6948 (3)0.2430 (4)0.6807 (4)0.0566 (13)
H200.75400.26430.68960.068*
C210.6690 (3)0.1654 (4)0.5962 (4)0.0488 (12)
H210.71030.13360.54650.059*
C220.5831 (2)0.1329 (3)0.5825 (3)0.0374 (9)
H220.56520.07910.52360.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0325 (5)0.0437 (6)0.0632 (7)0.0172 (4)0.0084 (5)0.0109 (5)
S10.0220 (5)0.0359 (5)0.0509 (6)0.0007 (4)0.0085 (4)0.0012 (4)
S20.0273 (5)0.0273 (5)0.0430 (6)0.0021 (4)0.0086 (4)0.0007 (4)
O10.0215 (13)0.0641 (19)0.063 (2)0.0002 (12)0.0001 (13)0.0002 (15)
O20.0421 (16)0.0354 (15)0.073 (2)0.0006 (12)0.0196 (15)0.0119 (14)
O30.0372 (15)0.0298 (14)0.0624 (19)0.0013 (12)0.0170 (14)0.0004 (13)
O40.0221 (14)0.0543 (17)0.067 (2)0.0025 (12)0.0014 (13)0.0214 (15)
C10.030 (2)0.046 (2)0.045 (2)0.0030 (17)0.0105 (18)0.0022 (19)
C20.0229 (18)0.0305 (18)0.038 (2)0.0010 (14)0.0032 (16)0.0033 (16)
C30.0296 (19)0.0289 (18)0.043 (2)0.0007 (15)0.0015 (17)0.0017 (17)
C40.0235 (17)0.0294 (18)0.040 (2)0.0053 (15)0.0033 (16)0.0032 (16)
C50.0254 (18)0.0278 (18)0.034 (2)0.0000 (14)0.0047 (16)0.0064 (16)
C60.032 (2)0.0277 (18)0.041 (2)0.0078 (15)0.0045 (17)0.0026 (17)
C70.0230 (18)0.0325 (19)0.046 (2)0.0066 (15)0.0019 (17)0.0022 (17)
C80.0258 (18)0.0282 (19)0.037 (2)0.0045 (15)0.0044 (16)0.0028 (16)
C90.0239 (18)0.036 (2)0.041 (2)0.0005 (15)0.0052 (16)0.0093 (17)
C100.0284 (19)0.0329 (19)0.032 (2)0.0003 (15)0.0050 (16)0.0034 (16)
C110.0225 (18)0.044 (2)0.049 (2)0.0000 (16)0.0069 (17)0.0151 (19)
C120.107 (4)0.068 (3)0.026 (2)0.048 (3)0.012 (3)0.002 (2)
C130.026 (2)0.044 (3)0.141 (5)0.0005 (19)0.023 (3)0.043 (3)
C140.095 (4)0.061 (3)0.072 (4)0.008 (3)0.031 (3)0.018 (3)
C150.094 (4)0.047 (3)0.046 (3)0.030 (3)0.011 (3)0.000 (2)
C160.029 (2)0.048 (2)0.063 (3)0.0016 (18)0.005 (2)0.020 (2)
C170.0255 (18)0.0270 (18)0.037 (2)0.0048 (14)0.0025 (16)0.0080 (16)
C180.040 (2)0.037 (2)0.044 (2)0.0001 (17)0.0027 (19)0.0038 (19)
C190.049 (3)0.055 (3)0.055 (3)0.011 (2)0.012 (2)0.009 (2)
C200.027 (2)0.068 (3)0.074 (3)0.009 (2)0.007 (2)0.029 (3)
C210.033 (2)0.056 (3)0.058 (3)0.016 (2)0.013 (2)0.028 (2)
C220.031 (2)0.038 (2)0.044 (2)0.0097 (17)0.0096 (18)0.0064 (18)
Geometric parameters (Å, º) top
Cl1—C41.739 (3)C11—C151.485 (6)
S1—O11.432 (3)C11—C121.551 (6)
S1—O21.434 (3)C11—H111.0000
S1—C11.753 (4)C12—C131.607 (7)
S1—C21.774 (3)C12—H12A0.9900
S2—C101.742 (4)C12—H12B0.9900
S2—C171.790 (4)C13—C141.425 (8)
O3—C81.213 (4)C13—C161.534 (6)
O4—C161.226 (4)C13—H131.0000
C1—H1A0.9800C14—C151.437 (7)
C1—H1B0.9800C14—H14A0.9900
C1—H1C0.9800C14—H14B0.9900
C2—C71.385 (5)C15—H15A0.9900
C2—C31.386 (5)C15—H15B0.9900
C3—C41.384 (5)C17—C181.382 (5)
C3—H30.9500C17—C221.385 (5)
C4—C51.385 (5)C18—C191.383 (6)
C5—C61.395 (5)C18—H180.9500
C5—C81.508 (5)C19—C201.387 (6)
C6—C71.384 (5)C19—H190.9500
C6—H60.9500C20—C211.365 (7)
C7—H70.9500C20—H200.9500
C8—C91.487 (5)C21—C221.383 (6)
C9—C101.363 (5)C21—H210.9500
C9—C161.476 (5)C22—H220.9500
C10—C111.517 (5)
O1—S1—O2119.16 (18)C11—C12—C1395.2 (3)
O1—S1—C1108.84 (18)C11—C12—H12A112.7
O2—S1—C1108.9 (2)C13—C12—H12A112.7
O1—S1—C2107.89 (18)C11—C12—H12B112.7
O2—S1—C2108.04 (16)C13—C12—H12B112.7
C1—S1—C2102.72 (17)H12A—C12—H12B110.2
C10—S2—C17103.94 (16)C14—C13—C16105.7 (5)
S1—C1—H1A109.5C14—C13—C12102.8 (4)
S1—C1—H1B109.5C16—C13—C12111.0 (3)
H1A—C1—H1B109.5C14—C13—H13112.2
S1—C1—H1C109.5C16—C13—H13112.2
H1A—C1—H1C109.5C12—C13—H13112.2
H1B—C1—H1C109.5C13—C14—C15108.8 (4)
C7—C2—C3121.3 (3)C13—C14—H14A109.9
C7—C2—S1120.4 (3)C15—C14—H14A109.9
C3—C2—S1118.3 (3)C13—C14—H14B109.9
C4—C3—C2118.4 (3)C15—C14—H14B109.9
C4—C3—H3120.8H14A—C14—H14B108.3
C2—C3—H3120.8C14—C15—C11107.1 (4)
C3—C4—C5121.9 (3)C14—C15—H15A110.3
C3—C4—Cl1116.1 (3)C11—C15—H15A110.3
C5—C4—Cl1121.8 (3)C14—C15—H15B110.3
C4—C5—C6118.3 (3)C11—C15—H15B110.3
C4—C5—C8124.4 (3)H15A—C15—H15B108.6
C6—C5—C8117.2 (3)O4—C16—C9121.8 (3)
C7—C6—C5120.9 (3)O4—C16—C13121.9 (4)
C7—C6—H6119.5C9—C16—C13116.1 (3)
C5—C6—H6119.5C18—C17—C22120.2 (3)
C6—C7—C2119.1 (3)C18—C17—S2120.6 (3)
C6—C7—H7120.4C22—C17—S2119.0 (3)
C2—C7—H7120.4C17—C18—C19120.1 (4)
O3—C8—C9120.9 (3)C17—C18—H18119.9
O3—C8—C5118.2 (3)C19—C18—H18119.9
C9—C8—C5120.9 (3)C18—C19—C20119.2 (4)
C10—C9—C16119.7 (3)C18—C19—H19120.4
C10—C9—C8120.7 (3)C20—C19—H19120.4
C16—C9—C8119.6 (3)C21—C20—C19120.8 (4)
C9—C10—C11119.4 (3)C21—C20—H20119.6
C9—C10—S2121.9 (3)C19—C20—H20119.6
C11—C10—S2118.7 (3)C20—C21—C22120.3 (4)
C15—C11—C10110.0 (3)C20—C21—H21119.9
C15—C11—C12103.2 (4)C22—C21—H21119.9
C10—C11—C12107.9 (3)C21—C22—C17119.5 (4)
C15—C11—H11111.8C21—C22—H22120.3
C10—C11—H11111.8C17—C22—H22120.3
C12—C11—H11111.8
O1—S1—C2—C737.9 (4)C17—S2—C10—C1119.8 (3)
O2—S1—C2—C7167.9 (3)C9—C10—C11—C1564.1 (5)
C1—S1—C2—C777.0 (3)S2—C10—C11—C15116.0 (4)
O1—S1—C2—C3145.0 (3)C9—C10—C11—C1247.8 (5)
O2—S1—C2—C314.9 (4)S2—C10—C11—C12132.1 (3)
C1—S1—C2—C3100.1 (3)C15—C11—C12—C1342.9 (4)
C7—C2—C3—C40.8 (6)C10—C11—C12—C1373.5 (4)
S1—C2—C3—C4177.9 (3)C11—C12—C13—C1444.6 (4)
C2—C3—C4—C51.5 (6)C11—C12—C13—C1668.0 (5)
C2—C3—C4—Cl1178.0 (3)C16—C13—C14—C1586.1 (5)
C3—C4—C5—C60.9 (6)C12—C13—C14—C1530.4 (5)
Cl1—C4—C5—C6177.3 (3)C13—C14—C15—C112.1 (5)
C3—C4—C5—C8174.6 (3)C10—C11—C15—C1486.7 (4)
Cl1—C4—C5—C81.8 (5)C12—C11—C15—C1428.3 (4)
C4—C5—C6—C70.4 (6)C10—C9—C16—O4177.3 (4)
C8—C5—C6—C7176.2 (3)C8—C9—C16—O41.1 (7)
C5—C6—C7—C21.0 (6)C10—C9—C16—C130.7 (6)
C3—C2—C7—C60.5 (6)C8—C9—C16—C13177.6 (4)
S1—C2—C7—C6176.6 (3)C14—C13—C16—O4106.6 (5)
C4—C5—C8—O3131.3 (4)C12—C13—C16—O4142.6 (5)
C6—C5—C8—O344.2 (5)C14—C13—C16—C976.9 (5)
C4—C5—C8—C946.5 (5)C12—C13—C16—C933.9 (6)
C6—C5—C8—C9138.0 (4)C10—S2—C17—C1874.3 (3)
O3—C8—C9—C1031.3 (6)C10—S2—C17—C22111.6 (3)
C5—C8—C9—C10146.4 (4)C22—C17—C18—C190.5 (6)
O3—C8—C9—C16147.0 (4)S2—C17—C18—C19174.5 (3)
C5—C8—C9—C1635.3 (5)C17—C18—C19—C201.0 (6)
C16—C9—C10—C115.7 (6)C18—C19—C20—C211.0 (7)
C8—C9—C10—C11176.0 (3)C19—C20—C21—C220.4 (6)
C16—C9—C10—S2174.2 (3)C20—C21—C22—C170.1 (6)
C8—C9—C10—S24.1 (5)C18—C17—C22—C210.1 (5)
C17—S2—C10—C9160.3 (3)S2—C17—C22—C21174.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O4i0.982.443.322 (4)150
C1—H1C···O4ii0.982.523.477 (5)165
C3—H3···O2iii0.952.533.422 (4)157
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y1/2, z+3/2; (iii) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O4i0.982.443.322 (4)150.0
C1—H1C···O4ii0.982.523.477 (5)165.3
C3—H3···O2iii0.952.533.422 (4)156.8
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y1/2, z+3/2; (iii) x, y+1, z+2.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).

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