Crystal structure of benzobi­cyclon

Kang, G.; Kim, J.; Lim, H.; Kim, T.H.

doi:10.1107/S2056989015023221

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Page o1035

https://doi.org/10.1107/S2056989015023221

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Crystal structure of benzobicyclon

Gihaeng Kang,^a Jineun Kim,^a ^* Hansu Lim ^a and Tae Ho Kim ^a ^*

^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).

Keywords: crystal structure; benzobicyclon; bicyclo[3.2.1]oct-2-en-4-one; herbicide.

CCDC reference: 1440215

1. Related literature

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 ).

2. Experimental

2.1. Crystal data

C₂₂H₁₉ClO₄S₂
M_r = 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 ) T_min = 0.687, T_max = 0.746
15850 measured reflections
3504 independent reflections
2584 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; 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).

Supporting information

CCDC reference: 1440215

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015023221/sj5485sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023221/sj5485Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023221/sj5485Isup3.cml

checkCIF report

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.

Structure description 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).

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

	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.
	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

C₂₂H₁₉ClO₄S₂	F(000) = 928
M_r = 446.94	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.5111 (8) Å	Cell parameters from 2645 reflections
b = 10.7218 (6) Å	θ = 2.6–24.7°
c = 12.0169 (6) Å	µ = 0.43 mm⁻¹
β = 91.449 (3)°	T = 173 K
V = 1997.85 (18) Å³	Block, colourless
Z = 4	0.15 × 0.11 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	2584 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.055
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 25.0°, θ_min = 2.3°
T_min = 0.687, T_max = 0.746	h = −18→18
15850 measured reflections	k = −11→12
3504 independent reflections	l = −14→12

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0619P)² + 2.0045P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3504 reflections	Δρ_max = 0.97 e Å⁻³
263 parameters	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₂₂H₁₉ClO₄S₂	V = 1997.85 (18) Å³
M_r = 446.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.5111 (8) Å	µ = 0.43 mm⁻¹
b = 10.7218 (6) Å	T = 173 K
c = 12.0169 (6) Å	0.15 × 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)
T_min = 0.687, T_max = 0.746	R_int = 0.055
15850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.07	Δρ_max = 0.97 e Å⁻³
3504 reflections	Δρ_min = −0.54 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	0.22882 (6)	0.40049 (9)	0.83242 (9)	0.0464 (3)
S1	−0.08667 (6)	0.26508 (9)	0.95779 (9)	0.0361 (3)
S2	0.41445 (6)	0.12501 (8)	0.64532 (8)	0.0324 (3)
O1	−0.16416 (16)	0.2346 (3)	0.8963 (2)	0.0495 (8)
O2	−0.07793 (17)	0.3867 (2)	1.0065 (3)	0.0499 (8)
O3	0.24478 (16)	0.0592 (2)	0.6713 (2)	0.0429 (7)
O4	0.14394 (16)	0.3801 (3)	0.5647 (3)	0.0479 (8)
C1	−0.0691 (2)	0.1524 (4)	1.0616 (3)	0.0401 (10)
H1A	−0.1083	0.1674	1.1228	0.060*
H1B	−0.0093	0.1576	1.0895	0.060*
H1C	−0.0799	0.0692	1.0304	0.060*
C2	0.0015 (2)	0.2413 (3)	0.8691 (3)	0.0303 (8)
C3	0.0716 (2)	0.3211 (3)	0.8792 (3)	0.0339 (9)
H3	0.0715	0.3884	0.9305	0.041*
C4	0.1417 (2)	0.3002 (3)	0.8126 (3)	0.0309 (8)
C5	0.1442 (2)	0.2011 (3)	0.7389 (3)	0.0290 (8)
C6	0.0730 (2)	0.1218 (3)	0.7314 (3)	0.0335 (9)
H6	0.0736	0.0530	0.6816	0.040*
C7	0.0013 (2)	0.1420 (3)	0.7954 (3)	0.0338 (9)
H7	−0.0473	0.0883	0.7890	0.041*
C8	0.2214 (2)	0.1671 (3)	0.6715 (3)	0.0302 (8)
C9	0.2696 (2)	0.2642 (3)	0.6103 (3)	0.0336 (9)
C10	0.3565 (2)	0.2546 (3)	0.5982 (3)	0.0310 (8)
C11	0.4045 (2)	0.3595 (4)	0.5419 (3)	0.0382 (9)
H11	0.4656	0.3361	0.5274	0.046*
C12	0.3542 (4)	0.3935 (5)	0.4330 (3)	0.0668 (16)
H12A	0.3347	0.3191	0.3906	0.080*
H12B	0.3870	0.4499	0.3845	0.080*
C13	0.2767 (3)	0.4631 (4)	0.4939 (5)	0.0711 (17)
H13	0.2407	0.5144	0.4411	0.085*
C14	0.3207 (4)	0.5376 (5)	0.5754 (5)	0.0755 (17)
H14A	0.2838	0.5499	0.6405	0.091*
H14B	0.3341	0.6204	0.5438	0.091*
C15	0.3992 (3)	0.4753 (4)	0.6092 (4)	0.0622 (14)
H15A	0.3983	0.4548	0.6895	0.075*
H15B	0.4495	0.5295	0.5958	0.075*
C16	0.2224 (2)	0.3702 (4)	0.5594 (4)	0.0466 (11)
C17	0.5234 (2)	0.1795 (3)	0.6555 (3)	0.0299 (8)
C18	0.5496 (3)	0.2579 (3)	0.7411 (3)	0.0404 (10)
H18	0.5085	0.2892	0.7914	0.048*
C19	0.6355 (3)	0.2910 (4)	0.7538 (4)	0.0532 (12)
H19	0.6536	0.3460	0.8118	0.064*
C20	0.6948 (3)	0.2430 (4)	0.6807 (4)	0.0566 (13)
H20	0.7540	0.2643	0.6896	0.068*
C21	0.6690 (3)	0.1654 (4)	0.5962 (4)	0.0488 (12)
H21	0.7103	0.1336	0.5465	0.059*
C22	0.5831 (2)	0.1329 (3)	0.5825 (3)	0.0374 (9)
H22	0.5652	0.0791	0.5236	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0325 (5)	0.0437 (6)	0.0632 (7)	−0.0172 (4)	0.0084 (5)	−0.0109 (5)
S1	0.0220 (5)	0.0359 (5)	0.0509 (6)	−0.0007 (4)	0.0085 (4)	−0.0012 (4)
S2	0.0273 (5)	0.0273 (5)	0.0430 (6)	0.0021 (4)	0.0086 (4)	0.0007 (4)
O1	0.0215 (13)	0.0641 (19)	0.063 (2)	0.0002 (12)	−0.0001 (13)	−0.0002 (15)
O2	0.0421 (16)	0.0354 (15)	0.073 (2)	−0.0006 (12)	0.0196 (15)	−0.0119 (14)
O3	0.0372 (15)	0.0298 (14)	0.0624 (19)	−0.0013 (12)	0.0170 (14)	−0.0004 (13)
O4	0.0221 (14)	0.0543 (17)	0.067 (2)	0.0025 (12)	0.0014 (13)	0.0214 (15)
C1	0.030 (2)	0.046 (2)	0.045 (2)	−0.0030 (17)	0.0105 (18)	0.0022 (19)
C2	0.0229 (18)	0.0305 (18)	0.038 (2)	−0.0010 (14)	0.0032 (16)	0.0033 (16)
C3	0.0296 (19)	0.0289 (18)	0.043 (2)	−0.0007 (15)	0.0015 (17)	−0.0017 (17)
C4	0.0235 (17)	0.0294 (18)	0.040 (2)	−0.0053 (15)	0.0033 (16)	0.0032 (16)
C5	0.0254 (18)	0.0278 (18)	0.034 (2)	0.0000 (14)	0.0047 (16)	0.0064 (16)
C6	0.032 (2)	0.0277 (18)	0.041 (2)	−0.0078 (15)	0.0045 (17)	−0.0026 (17)
C7	0.0230 (18)	0.0325 (19)	0.046 (2)	−0.0066 (15)	0.0019 (17)	0.0022 (17)
C8	0.0258 (18)	0.0282 (19)	0.037 (2)	−0.0045 (15)	0.0044 (16)	0.0028 (16)
C9	0.0239 (18)	0.036 (2)	0.041 (2)	0.0005 (15)	0.0052 (16)	0.0093 (17)
C10	0.0284 (19)	0.0329 (19)	0.032 (2)	0.0003 (15)	0.0050 (16)	0.0034 (16)
C11	0.0225 (18)	0.044 (2)	0.049 (2)	0.0000 (16)	0.0069 (17)	0.0151 (19)
C12	0.107 (4)	0.068 (3)	0.026 (2)	−0.048 (3)	0.012 (3)	0.002 (2)
C13	0.026 (2)	0.044 (3)	0.141 (5)	0.0005 (19)	−0.023 (3)	0.043 (3)
C14	0.095 (4)	0.061 (3)	0.072 (4)	0.008 (3)	0.031 (3)	0.018 (3)
C15	0.094 (4)	0.047 (3)	0.046 (3)	−0.030 (3)	0.011 (3)	0.000 (2)
C16	0.029 (2)	0.048 (2)	0.063 (3)	0.0016 (18)	0.005 (2)	0.020 (2)
C17	0.0255 (18)	0.0270 (18)	0.037 (2)	0.0048 (14)	0.0025 (16)	0.0080 (16)
C18	0.040 (2)	0.037 (2)	0.044 (2)	0.0001 (17)	0.0027 (19)	0.0038 (19)
C19	0.049 (3)	0.055 (3)	0.055 (3)	−0.011 (2)	−0.012 (2)	0.009 (2)
C20	0.027 (2)	0.068 (3)	0.074 (3)	−0.009 (2)	−0.007 (2)	0.029 (3)
C21	0.033 (2)	0.056 (3)	0.058 (3)	0.016 (2)	0.013 (2)	0.028 (2)
C22	0.031 (2)	0.038 (2)	0.044 (2)	0.0097 (17)	0.0096 (18)	0.0064 (18)

Geometric parameters (Å, º) top

Cl1—C4	1.739 (3)	C11—C15	1.485 (6)
S1—O1	1.432 (3)	C11—C12	1.551 (6)
S1—O2	1.434 (3)	C11—H11	1.0000
S1—C1	1.753 (4)	C12—C13	1.607 (7)
S1—C2	1.774 (3)	C12—H12A	0.9900
S2—C10	1.742 (4)	C12—H12B	0.9900
S2—C17	1.790 (4)	C13—C14	1.425 (8)
O3—C8	1.213 (4)	C13—C16	1.534 (6)
O4—C16	1.226 (4)	C13—H13	1.0000
C1—H1A	0.9800	C14—C15	1.437 (7)
C1—H1B	0.9800	C14—H14A	0.9900
C1—H1C	0.9800	C14—H14B	0.9900
C2—C7	1.385 (5)	C15—H15A	0.9900
C2—C3	1.386 (5)	C15—H15B	0.9900
C3—C4	1.384 (5)	C17—C18	1.382 (5)
C3—H3	0.9500	C17—C22	1.385 (5)
C4—C5	1.385 (5)	C18—C19	1.383 (6)
C5—C6	1.395 (5)	C18—H18	0.9500
C5—C8	1.508 (5)	C19—C20	1.387 (6)
C6—C7	1.384 (5)	C19—H19	0.9500
C6—H6	0.9500	C20—C21	1.365 (7)
C7—H7	0.9500	C20—H20	0.9500
C8—C9	1.487 (5)	C21—C22	1.383 (6)
C9—C10	1.363 (5)	C21—H21	0.9500
C9—C16	1.476 (5)	C22—H22	0.9500
C10—C11	1.517 (5)

O1—S1—O2	119.16 (18)	C11—C12—C13	95.2 (3)
O1—S1—C1	108.84 (18)	C11—C12—H12A	112.7
O2—S1—C1	108.9 (2)	C13—C12—H12A	112.7
O1—S1—C2	107.89 (18)	C11—C12—H12B	112.7
O2—S1—C2	108.04 (16)	C13—C12—H12B	112.7
C1—S1—C2	102.72 (17)	H12A—C12—H12B	110.2
C10—S2—C17	103.94 (16)	C14—C13—C16	105.7 (5)
S1—C1—H1A	109.5	C14—C13—C12	102.8 (4)
S1—C1—H1B	109.5	C16—C13—C12	111.0 (3)
H1A—C1—H1B	109.5	C14—C13—H13	112.2
S1—C1—H1C	109.5	C16—C13—H13	112.2
H1A—C1—H1C	109.5	C12—C13—H13	112.2
H1B—C1—H1C	109.5	C13—C14—C15	108.8 (4)
C7—C2—C3	121.3 (3)	C13—C14—H14A	109.9
C7—C2—S1	120.4 (3)	C15—C14—H14A	109.9
C3—C2—S1	118.3 (3)	C13—C14—H14B	109.9
C4—C3—C2	118.4 (3)	C15—C14—H14B	109.9
C4—C3—H3	120.8	H14A—C14—H14B	108.3
C2—C3—H3	120.8	C14—C15—C11	107.1 (4)
C3—C4—C5	121.9 (3)	C14—C15—H15A	110.3
C3—C4—Cl1	116.1 (3)	C11—C15—H15A	110.3
C5—C4—Cl1	121.8 (3)	C14—C15—H15B	110.3
C4—C5—C6	118.3 (3)	C11—C15—H15B	110.3
C4—C5—C8	124.4 (3)	H15A—C15—H15B	108.6
C6—C5—C8	117.2 (3)	O4—C16—C9	121.8 (3)
C7—C6—C5	120.9 (3)	O4—C16—C13	121.9 (4)
C7—C6—H6	119.5	C9—C16—C13	116.1 (3)
C5—C6—H6	119.5	C18—C17—C22	120.2 (3)
C6—C7—C2	119.1 (3)	C18—C17—S2	120.6 (3)
C6—C7—H7	120.4	C22—C17—S2	119.0 (3)
C2—C7—H7	120.4	C17—C18—C19	120.1 (4)
O3—C8—C9	120.9 (3)	C17—C18—H18	119.9
O3—C8—C5	118.2 (3)	C19—C18—H18	119.9
C9—C8—C5	120.9 (3)	C18—C19—C20	119.2 (4)
C10—C9—C16	119.7 (3)	C18—C19—H19	120.4
C10—C9—C8	120.7 (3)	C20—C19—H19	120.4
C16—C9—C8	119.6 (3)	C21—C20—C19	120.8 (4)
C9—C10—C11	119.4 (3)	C21—C20—H20	119.6
C9—C10—S2	121.9 (3)	C19—C20—H20	119.6
C11—C10—S2	118.7 (3)	C20—C21—C22	120.3 (4)
C15—C11—C10	110.0 (3)	C20—C21—H21	119.9
C15—C11—C12	103.2 (4)	C22—C21—H21	119.9
C10—C11—C12	107.9 (3)	C21—C22—C17	119.5 (4)
C15—C11—H11	111.8	C21—C22—H22	120.3
C10—C11—H11	111.8	C17—C22—H22	120.3
C12—C11—H11	111.8

O1—S1—C2—C7	−37.9 (4)	C17—S2—C10—C11	19.8 (3)
O2—S1—C2—C7	−167.9 (3)	C9—C10—C11—C15	64.1 (5)
C1—S1—C2—C7	77.0 (3)	S2—C10—C11—C15	−116.0 (4)
O1—S1—C2—C3	145.0 (3)	C9—C10—C11—C12	−47.8 (5)
O2—S1—C2—C3	14.9 (4)	S2—C10—C11—C12	132.1 (3)
C1—S1—C2—C3	−100.1 (3)	C15—C11—C12—C13	−42.9 (4)
C7—C2—C3—C4	0.8 (6)	C10—C11—C12—C13	73.5 (4)
S1—C2—C3—C4	177.9 (3)	C11—C12—C13—C14	44.6 (4)
C2—C3—C4—C5	−1.5 (6)	C11—C12—C13—C16	−68.0 (5)
C2—C3—C4—Cl1	−178.0 (3)	C16—C13—C14—C15	86.1 (5)
C3—C4—C5—C6	0.9 (6)	C12—C13—C14—C15	−30.4 (5)
Cl1—C4—C5—C6	177.3 (3)	C13—C14—C15—C11	2.1 (5)
C3—C4—C5—C8	−174.6 (3)	C10—C11—C15—C14	−86.7 (4)
Cl1—C4—C5—C8	1.8 (5)	C12—C11—C15—C14	28.3 (4)
C4—C5—C6—C7	0.4 (6)	C10—C9—C16—O4	177.3 (4)
C8—C5—C6—C7	176.2 (3)	C8—C9—C16—O4	−1.1 (7)
C5—C6—C7—C2	−1.0 (6)	C10—C9—C16—C13	0.7 (6)
C3—C2—C7—C6	0.5 (6)	C8—C9—C16—C13	−177.6 (4)
S1—C2—C7—C6	−176.6 (3)	C14—C13—C16—O4	106.6 (5)
C4—C5—C8—O3	131.3 (4)	C12—C13—C16—O4	−142.6 (5)
C6—C5—C8—O3	−44.2 (5)	C14—C13—C16—C9	−76.9 (5)
C4—C5—C8—C9	−46.5 (5)	C12—C13—C16—C9	33.9 (6)
C6—C5—C8—C9	138.0 (4)	C10—S2—C17—C18	74.3 (3)
O3—C8—C9—C10	−31.3 (6)	C10—S2—C17—C22	−111.6 (3)
C5—C8—C9—C10	146.4 (4)	C22—C17—C18—C19	0.5 (6)
O3—C8—C9—C16	147.0 (4)	S2—C17—C18—C19	174.5 (3)
C5—C8—C9—C16	−35.3 (5)	C17—C18—C19—C20	−1.0 (6)
C16—C9—C10—C11	5.7 (6)	C18—C19—C20—C21	1.0 (7)
C8—C9—C10—C11	−176.0 (3)	C19—C20—C21—C22	−0.4 (6)
C16—C9—C10—S2	−174.2 (3)	C20—C21—C22—C17	−0.1 (6)
C8—C9—C10—S2	4.1 (5)	C18—C17—C22—C21	0.1 (5)
C17—S2—C10—C9	−160.3 (3)	S2—C17—C22—C21	−174.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, z+1/2; (ii) −x, y−1/2, −z+3/2; (iii) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4ⁱ	0.98	2.44	3.322 (4)	150.0
C1—H1C···O4ⁱⁱ	0.98	2.52	3.477 (5)	165.3
C3—H3···O2ⁱⁱⁱ	0.95	2.53	3.422 (4)	156.8

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