2,2′-[o-Phenylenebis(methylenethio)]bis(pyridine N-oxide)

Zhang, C.-Y.; Gao, Q.; Cui, Y.; Xie, Y.-B.

doi:10.1107/S160053680902073X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1482

doi:10.1107/S160053680902073X

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2,2′-[o-Phenylenebis(methylenethio)]bis(pyridine N-oxide)

Chao-Yan Zhang,^a Qian Gao,^a Yue Cui ^a and Ya-Bo Xie ^a ^*

^aCollege of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100022, People's Republic of China
^*Correspondence e-mail: xieyabo@bjut.edu.cn

(Received 27 May 2009; accepted 1 June 2009; online 6 June 2009)

In the title compound, C₁₈H₁₆N₂O₂S₂, the benzene ring makes dihedral angles of 7.41 and 86.59° with the two outer pyridine N-oxygen rings. Two short intramolecular C—H⋯S contacts occur. The crystal packing is stabilized by C—H⋯O hydrogen bonds, C—H⋯π interactions and weak π–π staking interactions [centroid–centroid distance 3.7596 (7) Å].

Related literature

For a related stucture, see: Han et al. (2005 ). For thioether compounds, see: Xie et al. (2005 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₂S₂
M_r = 356.47
Monoclinic, P 2₁ /n
a = 7.5075 (15) Å
b = 17.810 (4) Å
c = 12.480 (3) Å
β = 105.20 (3)°
V = 1610.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 K
0.34 × 0.28 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
9681 measured reflections
3782 independent reflections
3145 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.083
S = 1.02
3782 reflections
225 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1ⁱ	0.93	2.42	3.133 (2)	134
C5—H5A⋯O1ⁱⁱ	0.93	2.38	3.253 (2)	155
C8—H8A⋯S1	0.93	2.67	3.1105 (18)	110
C11—H11A⋯S2	0.93	2.47	2.9322 (18)	111
C15—H15A⋯O2ⁱⁱⁱ	0.93	2.58	3.461 (2)	158
C9—H9A⋯Cg2^iv	0.93	2.90	3.645 (2)	138
Symmetry codes: (i) -x-1, -y, -z; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x, -y, -z+1. Cg2 is the centroid of the N2/C1–C5 ring.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902073X/at2798sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902073X/at2798Isup2.hkl

checkCIF report

Comment top

Thioether-type ligands are attracting great attention as the conformational freedom, flexible multidentate bridging ligands (Xie et al., 2005). In continuation of the structural study of thioether-type ligands (Han et al., 2005), herein, we report the crystal sructure of the title compound.

The title compound (Fig. 1) was obtained by the reaction of 2-mercaptopyridine N-oxide and o-xylylene dibromide. In the asymmetric unit, the central benzene ring makes dihedral angles of 7.44 and 86.52° with the two outer pyridine N-oxygen rings and the crystal packing is stabilized by C—H···O and C—H..S hydrogen bonding, C—H···π interactions (Table 1) and weak π-π staking interactions [centroid-to-centroid distance 3.7596 (7) Å].

Related literature top

For a related stucture, see: Han et al. (2005). For thioether compounds, see: Xie et al. (2005). Cg2 is the centroid of the N2/C1–C5 ring.

Experimental top

2-Mercaptopyridine N-oxide (1.2719 g, 10.00 mmol) was added to a stirred solution of KOH (0.6091 g, 10.85 mmol) in ethanol (50 ml). After 30 min, o-xylylene dibromide (1.3206 g, 5.00 mmol) was added and the mixture was heated to 343 K for 6 h with vigorous stirring. The mixture was cooled to room temperature and the precipitate was filtered off and washed with ethanol and water, giving a white powder in 66.0% yield. Then, a solution of the powder in CHCl₃/CH₃CN with a molar ratio of 1:1 was filtered. Slow diffusion of ether into the filtrate yielded colourless prism crystals.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-hydrogen atoms.

2,2'-[o-Phenylenebis(methylenethio)]bis(pyridine N-oxide) top

Crystal data top

C₁₈H₁₆N₂O₂S₂	F(000) = 744
M_r = 356.47	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9866 reflections
a = 7.5075 (15) Å	θ = 2.0–27.9°
b = 17.810 (4) Å	µ = 0.34 mm⁻¹
c = 12.480 (3) Å	T = 293 K
β = 105.20 (3)°	Prism, colourless
V = 1610.3 (7) Å³	0.34 × 0.28 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3145 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 27.9°, θ_min = 2.0°
ω scans	h = −8→9
9681 measured reflections	k = −17→23
3782 independent reflections	l = −15→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0371P)² + 0.5053P] where P = (F_o² + 2F_c²)/3
3782 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₂S₂	V = 1610.3 (7) Å³
M_r = 356.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5075 (15) Å	µ = 0.34 mm⁻¹
b = 17.810 (4) Å	T = 293 K
c = 12.480 (3) Å	0.34 × 0.28 × 0.16 mm
β = 105.20 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3145 reflections with I > 2σ(I)
9681 measured reflections	R_int = 0.017
3782 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.25 e Å⁻³
3782 reflections	Δρ_min = −0.20 e Å⁻³
225 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.17377 (5)	0.17901 (2)	0.34399 (3)	0.03675 (11)
S2	−0.30419 (5)	−0.03050 (2)	−0.04963 (3)	0.03289 (10)
C7	−0.00609 (19)	0.04497 (8)	0.25080 (11)	0.0304 (3)
N1	−0.47078 (17)	−0.01887 (7)	−0.25627 (10)	0.0350 (3)
O1	−0.48428 (16)	−0.09127 (6)	−0.24087 (9)	0.0458 (3)
C14	−0.38096 (18)	0.02425 (8)	−0.16810 (11)	0.0308 (3)
C6	0.0423 (2)	0.12465 (8)	0.22786 (12)	0.0335 (3)
C1	0.0008 (2)	0.20710 (8)	0.40531 (11)	0.0324 (3)
C12	−0.11785 (18)	0.00251 (8)	0.16387 (11)	0.0301 (3)
C15	−0.3632 (2)	0.10057 (9)	−0.18273 (13)	0.0397 (3)
H15A	−0.3009	0.1304	−0.1235	0.048*
N2	0.06622 (19)	0.25129 (7)	0.49662 (10)	0.0402 (3)
C2	−0.1847 (2)	0.18976 (9)	0.37257 (13)	0.0388 (3)
H2A	−0.2299	0.1592	0.3111	0.047*
C11	−0.1519 (2)	−0.07213 (9)	0.18381 (13)	0.0421 (4)
H11A	−0.2260	−0.1007	0.1270	0.051*
C13	−0.19734 (19)	0.03928 (8)	0.05228 (11)	0.0318 (3)
H13A	−0.0999	0.0646	0.0285	0.038*
H13B	−0.2883	0.0765	0.0587	0.038*
O2	0.24350 (18)	0.26652 (7)	0.52668 (10)	0.0570 (3)
C8	0.0643 (2)	0.01115 (9)	0.35310 (12)	0.0402 (3)
H8A	0.1367	0.0392	0.4112	0.048*
C9	0.0293 (3)	−0.06342 (10)	0.37091 (14)	0.0500 (4)
H9A	0.0787	−0.0852	0.4401	0.060*
C18	−0.5444 (2)	0.01241 (10)	−0.35676 (13)	0.0456 (4)
H18A	−0.6060	−0.0178	−0.4157	0.055*
C5	−0.0505 (3)	0.27874 (9)	0.55340 (14)	0.0536 (5)
H5A	−0.0048	0.3091	0.6151	0.064*
C3	−0.3033 (3)	0.21749 (10)	0.43040 (16)	0.0511 (4)
H3A	−0.4284	0.2060	0.4084	0.061*
C17	−0.5296 (3)	0.08746 (11)	−0.37289 (14)	0.0527 (4)
H17A	−0.5807	0.1085	−0.4424	0.063*
C16	−0.4379 (3)	0.13227 (10)	−0.28521 (14)	0.0507 (4)
H16A	−0.4269	0.1836	−0.2955	0.061*
C10	−0.0783 (3)	−0.10491 (10)	0.28622 (14)	0.0512 (4)
H10A	−0.1019	−0.1552	0.2975	0.061*
C4	−0.2338 (3)	0.26248 (10)	0.52122 (17)	0.0584 (5)
H4A	−0.3125	0.2819	0.5608	0.070*
H6A	0.125 (2)	0.1237 (9)	0.1798 (14)	0.042 (4)*
H6B	−0.062 (2)	0.1528 (10)	0.1903 (14)	0.043 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03174 (19)	0.0384 (2)	0.0364 (2)	−0.00423 (14)	0.00247 (14)	−0.00293 (15)
S2	0.03698 (19)	0.03129 (19)	0.02808 (18)	0.00011 (14)	0.00442 (14)	−0.00330 (13)
C7	0.0319 (7)	0.0324 (7)	0.0271 (7)	0.0032 (5)	0.0081 (5)	−0.0001 (5)
N1	0.0348 (6)	0.0363 (7)	0.0308 (6)	−0.0028 (5)	0.0034 (5)	−0.0047 (5)
O1	0.0547 (7)	0.0324 (6)	0.0443 (6)	−0.0074 (5)	0.0022 (5)	−0.0070 (5)
C14	0.0285 (7)	0.0351 (7)	0.0271 (7)	−0.0009 (5)	0.0044 (5)	−0.0038 (5)
C6	0.0403 (8)	0.0321 (7)	0.0267 (7)	0.0001 (6)	0.0064 (6)	−0.0010 (5)
C1	0.0395 (8)	0.0268 (7)	0.0277 (7)	−0.0026 (6)	0.0033 (6)	−0.0006 (5)
C12	0.0308 (7)	0.0320 (7)	0.0276 (7)	0.0021 (5)	0.0078 (5)	−0.0003 (5)
C15	0.0450 (9)	0.0357 (8)	0.0354 (8)	−0.0046 (6)	0.0054 (6)	−0.0039 (6)
N2	0.0555 (8)	0.0280 (6)	0.0312 (6)	−0.0053 (6)	0.0009 (6)	−0.0017 (5)
C2	0.0385 (8)	0.0371 (8)	0.0390 (8)	−0.0029 (6)	0.0069 (6)	−0.0036 (6)
C11	0.0507 (9)	0.0357 (8)	0.0365 (8)	−0.0049 (7)	0.0053 (7)	0.0004 (6)
C13	0.0333 (7)	0.0323 (7)	0.0271 (7)	−0.0009 (5)	0.0031 (5)	−0.0019 (5)
O2	0.0580 (8)	0.0494 (7)	0.0497 (7)	−0.0150 (6)	−0.0107 (6)	−0.0095 (6)
C8	0.0462 (9)	0.0415 (8)	0.0283 (7)	0.0008 (7)	0.0015 (6)	0.0019 (6)
C9	0.0655 (11)	0.0444 (9)	0.0351 (9)	0.0038 (8)	0.0046 (8)	0.0130 (7)
C18	0.0472 (9)	0.0530 (10)	0.0289 (8)	−0.0032 (8)	−0.0037 (6)	−0.0035 (7)
C5	0.0920 (15)	0.0324 (8)	0.0374 (9)	0.0016 (9)	0.0186 (9)	−0.0065 (7)
C3	0.0484 (10)	0.0446 (9)	0.0644 (12)	0.0024 (8)	0.0223 (9)	0.0019 (8)
C17	0.0617 (11)	0.0541 (11)	0.0348 (9)	−0.0003 (9)	−0.0004 (7)	0.0086 (7)
C16	0.0653 (11)	0.0380 (9)	0.0447 (10)	−0.0039 (8)	0.0071 (8)	0.0055 (7)
C10	0.0695 (12)	0.0348 (8)	0.0467 (10)	−0.0019 (8)	0.0104 (8)	0.0093 (7)
C4	0.0828 (14)	0.0410 (10)	0.0630 (12)	0.0088 (9)	0.0398 (11)	−0.0010 (8)

Geometric parameters (Å, º) top

S1—C1	1.7442 (15)	C2—C3	1.376 (2)
S1—C6	1.8061 (15)	C2—H2A	0.9300
S2—C14	1.7384 (15)	C11—C10	1.382 (2)
S2—C13	1.8084 (14)	C11—H11A	0.9300
C7—C8	1.385 (2)	C13—H13A	0.9700
C7—C12	1.4055 (19)	C13—H13B	0.9700
C7—C6	1.511 (2)	C8—C9	1.383 (2)
N1—O1	1.3116 (16)	C8—H8A	0.9300
N1—C18	1.351 (2)	C9—C10	1.367 (2)
N1—C14	1.3660 (17)	C9—H9A	0.9300
C14—C15	1.383 (2)	C18—C17	1.361 (3)
C6—H6A	0.971 (17)	C18—H18A	0.9300
C6—H6B	0.942 (18)	C5—C4	1.360 (3)
C1—N2	1.3658 (18)	C5—H5A	0.9300
C1—C2	1.380 (2)	C3—C4	1.374 (3)
C12—C11	1.389 (2)	C3—H3A	0.9300
C12—C13	1.5128 (19)	C17—C16	1.383 (2)
C15—C16	1.376 (2)	C17—H17A	0.9300
C15—H15A	0.9300	C16—H16A	0.9300
N2—O2	1.3130 (18)	C10—H10A	0.9300
N2—C5	1.355 (2)	C4—H4A	0.9300

C1—S1—C6	101.12 (7)	C12—C11—H11A	119.3
C14—S2—C13	101.52 (7)	C12—C13—S2	110.19 (10)
C8—C7—C12	118.93 (13)	C12—C13—H13A	109.6
C8—C7—C6	122.05 (13)	S2—C13—H13A	109.6
C12—C7—C6	118.93 (12)	C12—C13—H13B	109.6
O1—N1—C18	120.85 (12)	S2—C13—H13B	109.6
O1—N1—C14	118.39 (12)	H13A—C13—H13B	108.1
C18—N1—C14	120.76 (13)	C9—C8—C7	121.54 (14)
N1—C14—C15	119.39 (13)	C9—C8—H8A	119.2
N1—C14—S2	110.69 (10)	C7—C8—H8A	119.2
C15—C14—S2	129.92 (11)	C10—C9—C8	119.57 (15)
C7—C6—S1	117.35 (10)	C10—C9—H9A	120.2
C7—C6—H6A	109.0 (10)	C8—C9—H9A	120.2
S1—C6—H6A	101.6 (10)	N1—C18—C17	120.86 (15)
C7—C6—H6B	112.7 (10)	N1—C18—H18A	119.6
S1—C6—H6B	108.7 (10)	C17—C18—H18A	119.6
H6A—C6—H6B	106.4 (14)	N2—C5—C4	120.81 (16)
N2—C1—C2	119.34 (14)	N2—C5—H5A	119.6
N2—C1—S1	112.67 (11)	C4—C5—H5A	119.6
C2—C1—S1	127.99 (12)	C4—C3—C2	118.96 (17)
C11—C12—C7	118.52 (13)	C4—C3—H3A	120.5
C11—C12—C13	122.19 (13)	C2—C3—H3A	120.5
C7—C12—C13	119.29 (12)	C18—C17—C16	119.52 (16)
C16—C15—C14	119.74 (14)	C18—C17—H17A	120.2
C16—C15—H15A	120.1	C16—C17—H17A	120.2
C14—C15—H15A	120.1	C15—C16—C17	119.72 (16)
O2—N2—C5	121.49 (14)	C15—C16—H16A	120.1
O2—N2—C1	118.23 (13)	C17—C16—H16A	120.1
C5—N2—C1	120.27 (14)	C9—C10—C11	119.92 (15)
C3—C2—C1	120.38 (15)	C9—C10—H10A	120.0
C3—C2—H2A	119.8	C11—C10—H10A	120.0
C1—C2—H2A	119.8	C5—C4—C3	120.23 (17)
C10—C11—C12	121.50 (15)	C5—C4—H4A	119.9
C10—C11—H11A	119.3	C3—C4—H4A	119.9

O1—N1—C14—C15	179.24 (13)	S1—C1—C2—C3	−179.40 (13)
C18—N1—C14—C15	−1.0 (2)	C7—C12—C11—C10	−0.2 (2)
O1—N1—C14—S2	−0.70 (16)	C13—C12—C11—C10	180.00 (15)
C18—N1—C14—S2	179.09 (12)	C11—C12—C13—S2	−9.11 (17)
C13—S2—C14—N1	−178.90 (10)	C7—C12—C13—S2	171.08 (10)
C13—S2—C14—C15	1.17 (16)	C14—S2—C13—C12	−179.41 (9)
C8—C7—C6—S1	−7.41 (19)	C12—C7—C8—C9	1.0 (2)
C12—C7—C6—S1	176.13 (10)	C6—C7—C8—C9	−175.47 (15)
C1—S1—C6—C7	−80.37 (12)	C7—C8—C9—C10	−0.5 (3)
C6—S1—C1—N2	−178.97 (10)	O1—N1—C18—C17	−179.67 (16)
C6—S1—C1—C2	1.27 (15)	C14—N1—C18—C17	0.5 (2)
C8—C7—C12—C11	−0.6 (2)	O2—N2—C5—C4	179.98 (16)
C6—C7—C12—C11	175.95 (13)	C1—N2—C5—C4	0.5 (2)
C8—C7—C12—C13	179.20 (13)	C1—C2—C3—C4	−0.1 (3)
C6—C7—C12—C13	−4.23 (19)	N1—C18—C17—C16	0.0 (3)
N1—C14—C15—C16	0.8 (2)	C14—C15—C16—C17	−0.3 (3)
S2—C14—C15—C16	−179.24 (13)	C18—C17—C16—C15	−0.1 (3)
C2—C1—N2—O2	179.46 (13)	C8—C9—C10—C11	−0.3 (3)
S1—C1—N2—O2	−0.33 (17)	C12—C11—C10—C9	0.7 (3)
C2—C1—N2—C5	−1.0 (2)	N2—C5—C4—C3	0.2 (3)
S1—C1—N2—C5	179.20 (12)	C2—C3—C4—C5	−0.4 (3)
N2—C1—C2—C3	0.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.93	2.42	3.133 (2)	134
C5—H5A···O1ⁱⁱ	0.93	2.38	3.253 (2)	155
C8—H8A···S1	0.93	2.67	3.1105 (18)	110
C11—H11A···S2	0.93	2.47	2.9322 (18)	111
C15—H15A···O2ⁱⁱⁱ	0.93	2.58	3.461 (2)	158
C9—H9A···Cg2^iv	0.93	2.90	3.645 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₂S₂
M_r	356.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.5075 (15), 17.810 (4), 12.480 (3)
β (°)	105.20 (3)
V (Å³)	1610.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.34 × 0.28 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9681, 3782, 3145
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.02
No. of reflections	3782
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.9300	2.4200	3.133 (2)	134.00
C5—H5A···O1ⁱⁱ	0.9300	2.3800	3.253 (2)	155.00
C8—H8A···S1	0.9300	2.6700	3.1105 (18)	110.00
C11—H11A···S2	0.9300	2.4700	2.9322 (18)	111.00
C15—H15A···O2ⁱⁱⁱ	0.9300	2.5800	3.461 (2)	158.00
C9—H9A···Cg2^iv	0.93	2.90	3.645 (2)	138

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

Acknowledgements

This work was supported Beijing Municipal Natural Science Foundation (grant No. 2082004).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Han, L., Wu, B. L., Xu, Y. Q., Wu, M. Y., Gong, Y. Q., Lou, B. Y., Chen, B. Q. & Hong, M. C. (2005). Inorg. Chim. Acta, 358, 2005–2013. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, Y. B., Li, J. R. & Bu, X. H. (2005). Polyhedron, 24, 413–418. Web of Science CSD CrossRef CAS Google Scholar