Crystal structure of N,N'-bis-[3-(methyl-sulfan-yl)prop-yl]-1,8:4,5-naphthalene-tetra-carb-oxy-lic di-imide.

The title compound, C22H22N2O4S2, was synthesized by the reaction of 1,4,5,8-naphthalene-tetra-carb-oxy-lic dianhydride with 3-(methyl-sulfan-yl)propyl-amine. The whole mol-ecule is generated by an inversion operation of the asymmetric unit. This mol-ecule has an anti form with the terminal methyl-thio-propyl groups above and below the aromatic di-imide plane, where four intra-molecular C-H⋯O and C-H⋯S hydrogen bonds are present and the O⋯H⋯S angle is 100.8°. DFT calculations revealed slight differences between the solid state and gas phase structures. In the crystal, C-H⋯O and C-H⋯S hydrogen bonds link the mol-ecules into chains along the [2 direction. adjacent chains are inter-connected by π-π inter-actions, forming a two-dimensional network parallel to the (001) plane. Each two-dimensional layer is further packed in an ABAB sequence along the c-axis direction. Hirshfeld surface analysis shows that van der Waals inter-actions make important contributions to the inter-molecular contacts. The most important contacts found in the Hirshfeld surface analysis are H⋯H (44.2%), H⋯O/O⋯H (18.2%), H⋯C/C⋯H (14.4%), and H⋯S/S⋯H (10.2%).

Chemical context

Naphthalene di­imide, which has an expanded π-electron-deficient plane has attracted considerable inter­est as an excellent organic linker material for the production of photochromic coordination polymers as a result of their photoinduced electron transfer from neutral organic moieties to stable anionic radicals (Liu et al., 2018 ▸). Aromatic imides are highly fluorescent residues that are used in the signal generation of sensors or on–off mol­ecular switches. They have also been used in the design of receptors (Claudio-Catalán et al., 2016 ▸) and sensors to recognize charged species and other guests (Landey-Álvarez et al., 2016 ▸). In addition, naphthalene di­imides are ideal for studying anionic⋯π inter­actions because the quadrupole moments are highly positive (Fang et al., 2015 ▸). We have extended our work on naphthalene di­imides to produce the title compound by the reaction of naphthalene­carb­oxy­lic dianhydride with methyl­thio­pyrimidine and report its crystal structure here.

Structural commentary

The title compound comprises a central naphthalene di­imide with terminal thio­propyl chains (Fig. 1 ▸). The mol­ecule lies on a crystallographic inversion center located at the centroid of the naphthalene ring system and the asymmetric unit is composed of one half of the mol­ecule. As expected, the naphthalene di­imide plane (N1/C5/O1/C6/C10/C7/C8/C11/C9/O2) is roughly planar with an r.m.s. deviation of 0.024 Å. The total distance between the terminal carbon atoms is 18.621 Å. Furthermore, this mol­ecule has an anti form as a result of the intra­molecular C4—H4A⋯O1 and C4—H4A⋯S1 hydrogen bonds (Table 1 ▸). The terminal methyl­thio­propyl­amine group is fixed at an O1⋯H4A⋯S1 angle of 100.8° by the aforementioned intra­molecular hydrogen bonds. The C3/C2/S1/C1 section of the methyl­thio­propyl substituent is almost parallel to the naphthalene di­imide unit with the C3/C2/S1/C1 mean plane inclined to the naphthalene di­imide plane at a dihedral angle of 13.1 (2)°.

Figure 1

The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius and yellow and green dashed lines represent intra­molecular C—H⋯S and C—H⋯O hydrogen bonds, respectively. Unlabelled atoms are generated by the symmetry operation (−x + 2, −y + 1, −z).

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯S1	0.99	2.84	3.300 (2)	109
C4—H4A⋯O1	0.99	2.32	2.688 (3)	101
C10—H10⋯O1i	0.95	2.39	3.316 (3)	164
C11—H11⋯S1ii	0.95	2.86	3.779 (2)	162

Symmetry codes: (i) ; (ii) .

Theoretical calculations

DFT calculations were performed using the GAUSSIAN09 software package (Frisch et al., 2009 ▸) and the calculated distances and angles were compared with experimental values from the X-ray diffraction studies. The overall structural calculation was performed using the B3LYP level theory with a 6–311++G** basis set. The parameters optimized for bond lengths and bond angles are in close agreement with experimental crystallographic data (Table 2 ▸). The terminal methyl­thio­propyl group is fixed by inter­nal hydrogen bonding in the crystal, whereas its inter­nal hydrogen bonds are broken in the gas-phase structural calculation. This can be confirmed by the fact that the O1⋯H4A⋯S1 angle of the methyl­thio­propyl group has changed from 100.8 to 122.0° (Fig. 2 ▸). However, even in the gas phase the mol­ecule has an anti form similar to that found in the solid state.

Table 2

Experimental and calculated bond lengths (Å)

Bond	X-ray	B3LYP (6–311++G**)
O1—C5	1.210 (3)	1.2158
O2—C9	1.221 (3)	1.2173
N1—C4	1.471 (3)	1.4779
N1—C5	1.404 (3)	1.4047
N1—C9	1.394 (3)	1.4029
S1—C1	1.785 (3)	1.8244
S1—C2	1.803 (2)	1.8399
C2—C3	1.523 (3)	1.5301
C3—C4	1.521 (3)	1.5341
C5—C6	1.479 (3)	1.4880
C6—C7	1.408 (3)	1.4135
C7—C8	1.415 (3)	1.4136
C8—C9	1.478 (3)	1.4877
C6—C10	1.381 (3)	1.3835
C8—C11	1.373 (3)	1.3835

Figure 2

Atom-by-atom superimposition of the calculated structure (blue) using B3LYP/6–311++G** and the X-ray structure (green) for the title compound.

Supra­molecular features

In the crystal, C—H⋯O and C—H⋯S hydrogen bonds (Table 1 ▸) link the mol­ecules, forming (11) and (10) rings (Fig. 3 ▸) and resulting in chains along the [20] direction. Adjacent chains are linked by inter­molecular π–π inter­actions between naphthalene di­imide rings [Cg1⋯Cg2 = 3.5756 (12) Å; Cg1 and Cg2 are the centroids of the C6/C7/C7iii/C8iii/C10/C11iii and C6iv/C7iv/C7v/C8v/C10iv/C11v rings, respectively; symmetry codes: (iii) −x + 2, −y + 1, −z; (iv) −x + 2, −y, −z; (v) x, y − 1, z]. These π–π inter­actions lead to a two-dimensional network structure parallel to the (001) plane (Fig. 4 ▸). The network structures are stacked in an alternating ABAB sequence along the c-axis direction (Fig. 5 ▸).

Figure 3

Inter­molecular C—H⋯S and C—H⋯O hydrogen bonds (yellow and green dashed lines) forming chains along the [20] direction with (11) and (10) motifs.

Figure 4

A packing diagram for the title compound, showing the two-dimensional network formed by C—H⋯S and C—H⋯O hydrogen bonds (yellow and green dashed lines) and π–π inter­actions (black dashed lines). H atoms not involved in inter­molecular inter­actions have been omitted for clarity.

Figure 5

Packing diagrams of the title compound showing (a) the ABAB stacking pattern and (b) the two-dimensional structure.

Hirshfeld surface analysis

Hirshfeld surface analysis was performed using CrystalExplorer (Turner et al., 2017 ▸) to qu­antify the various inter­molecular inter­actions in the mol­ecular packing of the title compound. The bright red dots in Fig. 6 ▸ showing the Hirshfeld surface mapped to the normalized contact distance (d norm) indicate the (11) and (10) loops, and the contact points of the inter­molecular C—H⋯O and C—H⋯S hydrogen bonds. The lighter red dot on the surface represents the π–π inter­action with adjacent mol­ecules. The white and blue colours that make up the majority of the surface indicate contact distances that are equal to or greater than the van der Waals radii.

Figure 6

A view of the Hirshfeld surface of the title compound mapped over d norm, showing the H⋯S and H⋯O contacts of the inter­molecular inter­actions using a fixed colour scale of −0.2580 (red) to 1.0789 (blue) a.u.

The C—H⋯O and C—H⋯S hydrogen bonds and π–π stacking inter­actions are identified in the two-dimensional fingerprint plots (Fig. 7 ▸ a–e), which show the H⋯H, H⋯C/C⋯H, H⋯O/ O⋯H, H⋯N/N⋯H, and H⋯S/S⋯H contacts. The relative contributions of the atomic contacts to the Hirshfeld surface are summarized in Table 3 ▸. These show that the dominant inter­action, accounting for 44.2% of the surface, is the H⋯H van der Waals inter­action. Substantial contributions are also made by H⋯O/O⋯H (18.3%), H⋯C/C⋯H (14.4%), and H⋯S/S⋯H (10.2%) contacts, which are indicated by two sharp peaks in each fingerprint plot. Lesser contributions from C⋯O/O⋯C, C⋯C, H⋯N/N⋯H, O⋯O, N⋯O/O⋯N, and C⋯S/S⋯C contacts are included in Table 3 ▸ for completeness.

Figure 7

(a) The full two-dimensional fingerprint plot for the title compound and those delineated into (b) H⋯H, (c) H⋯O/O⋯H, (d) H⋯C/C⋯H and (e) H⋯S/S⋯H contacts. The d i and d e values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface contacts.

Table 3

Percentage contributions of inter­atomic contacts to the Hirshfeld surface of the title compound.

Contact	Percentage contribution
H⋯H	44.2
H⋯O/O⋯H	18.3
H⋯C/C⋯H	14.4
H⋯S/S⋯H	10.2
C⋯O/O⋯C	5.6
C⋯C	4.5
H⋯N/N⋯H	1.4
O⋯O	0.5
N⋯O/O⋯N	0.4
C⋯S/S⋯C	0.4

Synthesis and crystallization

A mixture of 1,4,5,8-naphthalene­tetra­carb­oxy­lic dianhydride (6.70 g, 25.0 mmol) and 3-(methyl­sulfan­yl)propyl­amine (5.6 mL, 50.0 mmol) in toluene (5 mL) and quinoline (15 mL) was heated at 453 K with stirring for 1h. Upon cooling to room temperature, a golden yellow crude solid was filtered off and washed with diethyl ether. A golden yellow powder was obtained. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a di­chloro­methane solution of the title compound.

1H NMR (300 MHz, CDCl3): δ 8.77 (s, 2H, Ar), 4.33 (t, 2H, CH2N), 2.64 (t, 2H, CH2), 2.14 (s, 3H, CH3), 2.07 (t, 2H, CH2S). 13C NMR (75.4 MHz, CDCl3): δ 162.81, 130.99, 126.69, 126.57, 40.01, 31.61, 27.16 and 15.31. IR (ν, cm−1): 3344 (m); 3071 (m); 2916 (s); 2848 (s); 1999 (s); 1693 (s).

Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, updated February 2019; Groom et al., 2016 ▸) for naphthalene di­imide derivatives gave 31 hits for structures that include a terminal propyl group. The title compound was not found. Related compounds include a series of cyclo­alkyl-substituted naphthalene tetra­carb­oxy­lic di­imides (Kakinuma et al., 2013 ▸). Other terminal n-alkyl groups are known with 2,7-di­butyl­benzo[lmn][3,8]phenanthroline-1,3,6,8-tetra­one (Alvey et al., 2010 ▸), bis-N,N′-di­pentyl­naphthalene-1,4,5,8-tetra­carb­oxy­lic di­imide (Andric et al., 2004 ▸), N,N′-di-n-hexyl-1,4;5,8-naphthalene­tetra­carb­oxy­lic di­imide (Ofir et al., 2006 ▸), and N,N′-di(n-dodec­yl)naphthalene-4,5,8,9-tetra­carb­oxy­lic acid di­imide (Kozycz et al., 2015 ▸).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. All H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, U iso = 1.2U eq(C) for aromatic, d(C—H) = 0.99 Å, U iso = 1.2U eq(C) for methyl­ene, and d(C—H) = 0.98 Å, U iso = 1.5U eq(C) for the methyl H atoms.

Table 4

Experimental details

Crystal data
Chemical formula	C22H22N2O4S2
M r	442.53
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	173
a, b, c (Å)	8.0500 (2), 4.9407 (1), 24.9626 (7)
β (°)	94.333 (2)
V (Å3)	989.99 (4)
Z	2
Radiation type	Mo Kα
μ (mm−1)	0.30
Crystal size (mm)	0.23 × 0.05 × 0.04
Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 ▸)
T min, T max	0.676, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	5641, 1732, 1360
R int	0.046
(sin θ/λ)max (Å−1)	0.595
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.042, 0.101, 1.05
No. of reflections	1732
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.25, −0.26

Computer programs: APEX2 and SAINT (Bruker, 2014 ▸), SHELXS97 and SHELXTL (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸), DIAMOND (Brandenburg, 2010 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989019007771/sj5571sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019007771/sj5571Isup2.hkl

CCDC reference: 1919395

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H22N2O4S2	F(000) = 464
Mr = 442.53	Dx = 1.485 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0500 (2) Å	Cell parameters from 1676 reflections
b = 4.9407 (1) Å	θ = 3.1–26.1°
c = 24.9626 (7) Å	µ = 0.30 mm−1
β = 94.333 (2)°	T = 173 K
V = 989.99 (4) Å3	Rod, yellow
Z = 2	0.23 × 0.05 × 0.04 mm

Bruker APEXII CCD diffractometer	1360 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.046
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 25.0°, θmin = 1.6°
Tmin = 0.676, Tmax = 0.746	h = −9→9
5641 measured reflections	k = −5→5
1732 independent reflections	l = −29→25

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.3426P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1732 reflections	Δρmax = 0.25 e Å−3
137 parameters	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.25895 (9)	0.32924 (13)	0.17605 (3)	0.0356 (2)
O1	0.5336 (2)	0.2804 (3)	0.04996 (7)	0.0310 (4)
O2	0.8407 (2)	0.9669 (3)	0.12693 (6)	0.0326 (5)
N1	0.6852 (2)	0.6297 (4)	0.08708 (8)	0.0243 (5)
C1	0.0764 (4)	0.4611 (6)	0.20299 (12)	0.0458 (8)
H1A	0.0888	0.4506	0.2423	0.069*
H1B	−0.0207	0.3548	0.1895	0.069*
H1C	0.0609	0.6503	0.1919	0.069*
C2	0.4130 (3)	0.5621 (5)	0.20506 (10)	0.0273 (6)
H2A	0.3685	0.7488	0.2024	0.033*
H2B	0.4374	0.5191	0.2436	0.033*
C3	0.5728 (3)	0.5448 (5)	0.17623 (9)	0.0276 (6)
H3A	0.6650	0.6315	0.1985	0.033*
H3B	0.6023	0.3526	0.1710	0.033*
C4	0.5500 (3)	0.6857 (5)	0.12200 (10)	0.0274 (6)
H4A	0.4431	0.6269	0.1035	0.033*
H4B	0.5434	0.8834	0.1279	0.033*
C5	0.6592 (3)	0.4151 (4)	0.05056 (9)	0.0243 (6)
C6	0.7912 (3)	0.3668 (4)	0.01356 (9)	0.0214 (5)
C7	0.9374 (3)	0.5241 (4)	0.01778 (8)	0.0200 (5)
C8	0.9613 (3)	0.7304 (4)	0.05690 (9)	0.0228 (5)
C9	0.8287 (3)	0.7878 (4)	0.09317 (9)	0.0249 (6)
C10	0.7698 (3)	0.1661 (4)	−0.02484 (9)	0.0234 (5)
H10	0.6712	0.0598	−0.0273	0.028*
C11	1.1054 (3)	0.8802 (4)	0.06017 (9)	0.0242 (6)
H11	1.1210	1.0173	0.0868	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.0366 (5)	0.0304 (4)	0.0400 (4)	−0.0049 (3)	0.0038 (3)	−0.0064 (3)
O1	0.0268 (11)	0.0293 (9)	0.0371 (10)	−0.0088 (8)	0.0036 (8)	−0.0010 (8)
O2	0.0372 (11)	0.0284 (9)	0.0322 (10)	−0.0041 (8)	0.0025 (8)	−0.0113 (8)
N1	0.0252 (12)	0.0200 (10)	0.0273 (11)	−0.0021 (9)	0.0009 (9)	−0.0004 (8)
C1	0.0360 (19)	0.0483 (17)	0.0541 (19)	−0.0024 (14)	0.0104 (14)	0.0018 (15)
C2	0.0320 (16)	0.0220 (12)	0.0276 (13)	−0.0002 (11)	−0.0003 (11)	−0.0003 (10)
C3	0.0292 (15)	0.0272 (13)	0.0260 (13)	0.0017 (11)	−0.0011 (11)	−0.0019 (10)
C4	0.0254 (15)	0.0255 (13)	0.0314 (14)	0.0034 (11)	0.0038 (11)	0.0005 (11)
C5	0.0275 (15)	0.0199 (12)	0.0247 (13)	−0.0006 (11)	−0.0034 (10)	0.0039 (10)
C6	0.0237 (14)	0.0150 (11)	0.0248 (13)	0.0001 (10)	−0.0031 (10)	0.0028 (9)
C7	0.0226 (14)	0.0152 (11)	0.0214 (12)	−0.0006 (10)	−0.0037 (9)	0.0028 (9)
C8	0.0253 (14)	0.0178 (11)	0.0246 (13)	−0.0015 (10)	−0.0026 (10)	0.0028 (9)
C9	0.0284 (15)	0.0211 (12)	0.0246 (13)	0.0008 (10)	−0.0021 (10)	0.0034 (10)
C10	0.0220 (14)	0.0198 (12)	0.0273 (13)	−0.0028 (10)	−0.0065 (10)	0.0044 (10)
C11	0.0302 (15)	0.0177 (11)	0.0236 (13)	−0.0019 (10)	−0.0045 (10)	−0.0018 (9)

S1—C1	1.785 (3)	C3—H3B	0.9900
S1—C2	1.803 (2)	C4—H4A	0.9900
O1—C5	1.210 (3)	C4—H4B	0.9900
O2—C9	1.221 (3)	C5—C6	1.479 (3)
N1—C9	1.394 (3)	C6—C10	1.381 (3)
N1—C5	1.404 (3)	C6—C7	1.408 (3)
N1—C4	1.471 (3)	C7—C7i	1.413 (4)
C1—H1A	0.9800	C7—C8	1.415 (3)
C1—H1B	0.9800	C8—C11	1.373 (3)
C1—H1C	0.9800	C8—C9	1.478 (3)
C2—C3	1.523 (3)	C10—C11i	1.404 (3)
C2—H2A	0.9900	C10—H10	0.9500
C2—H2B	0.9900	C11—C10i	1.404 (3)
C3—C4	1.521 (3)	C11—H11	0.9500
C3—H3A	0.9900
C1—S1—C2	100.17 (12)	N1—C4—H4B	108.9
C9—N1—C5	125.2 (2)	C3—C4—H4B	108.9
C9—N1—C4	118.31 (19)	H4A—C4—H4B	107.7
C5—N1—C4	116.52 (19)	O1—C5—N1	120.4 (2)
S1—C1—H1A	109.5	O1—C5—C6	122.9 (2)
S1—C1—H1B	109.5	N1—C5—C6	116.7 (2)
H1A—C1—H1B	109.5	C10—C6—C7	120.5 (2)
S1—C1—H1C	109.5	C10—C6—C5	119.5 (2)
H1A—C1—H1C	109.5	C7—C6—C5	120.0 (2)
H1B—C1—H1C	109.5	C6—C7—C7i	119.5 (2)
C3—C2—S1	110.75 (16)	C6—C7—C8	121.3 (2)
C3—C2—H2A	109.5	C7i—C7—C8	119.3 (3)
S1—C2—H2A	109.5	C11—C8—C7	120.0 (2)
C3—C2—H2B	109.5	C11—C8—C9	120.4 (2)
S1—C2—H2B	109.5	C7—C8—C9	119.6 (2)
H2A—C2—H2B	108.1	O2—C9—N1	120.2 (2)
C4—C3—C2	110.2 (2)	O2—C9—C8	122.6 (2)
C4—C3—H3A	109.6	N1—C9—C8	117.2 (2)
C2—C3—H3A	109.6	C6—C10—C11i	119.7 (2)
C4—C3—H3B	109.6	C6—C10—H10	120.1
C2—C3—H3B	109.6	C11i—C10—H10	120.1
H3A—C3—H3B	108.1	C8—C11—C10i	121.1 (2)
N1—C4—C3	113.37 (19)	C8—C11—H11	119.5
N1—C4—H4A	108.9	C10i—C11—H11	119.5
C3—C4—H4A	108.9
C1—S1—C2—C3	−163.99 (17)	C6—C7—C8—C11	179.8 (2)
S1—C2—C3—C4	75.4 (2)	C7i—C7—C8—C11	−0.3 (4)
C9—N1—C4—C3	−84.9 (2)	C6—C7—C8—C9	−1.7 (3)
C5—N1—C4—C3	94.0 (2)	C7i—C7—C8—C9	178.1 (2)
C2—C3—C4—N1	−167.95 (19)	C5—N1—C9—O2	−178.5 (2)
C9—N1—C5—O1	176.4 (2)	C4—N1—C9—O2	0.3 (3)
C4—N1—C5—O1	−2.5 (3)	C5—N1—C9—C8	2.2 (3)
C9—N1—C5—C6	−4.1 (3)	C4—N1—C9—C8	−178.94 (19)
C4—N1—C5—C6	177.07 (18)	C11—C8—C9—O2	0.0 (3)
O1—C5—C6—C10	2.3 (3)	C7—C8—C9—O2	−178.4 (2)
N1—C5—C6—C10	−177.28 (19)	C11—C8—C9—N1	179.24 (19)
O1—C5—C6—C7	−177.5 (2)	C7—C8—C9—N1	0.8 (3)
N1—C5—C6—C7	3.0 (3)	C7—C6—C10—C11i	−0.4 (3)
C10—C6—C7—C7i	0.2 (4)	C5—C6—C10—C11i	179.8 (2)
C5—C6—C7—C7i	179.9 (2)	C7—C8—C11—C10i	0.5 (3)
C10—C6—C7—C8	−179.9 (2)	C9—C8—C11—C10i	−177.9 (2)
C5—C6—C7—C8	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···S1	0.99	2.84	3.300 (2)	109
C4—H4A···O1	0.99	2.32	2.688 (3)	101
C10—H10···O1ii	0.95	2.39	3.316 (3)	164
C11—H11···S1iii	0.95	2.86	3.779 (2)	162