Triethyl-ammonium (S)-(-)-O-[1-(2-naphth-yl)eth-yl] (4-meth-oxy-phen-yl)dithio-phospho-nate.

The crystal structure of the title compound, C(6)H(16)N(+)·C(19)H(18)O(2)PS(2) (-), consists of the dithio-phospho-nate anions and the triethyl-ammonium cations, which are linked by N-H⋯S hydrogen bonds and weak C-H⋯O hydrogen bonds. In the anion, the benzene ring is oriented with respect to the naphthalene ring system at a dihedral angle of 24.92 (5)°. In the crystal, weak C-H⋯π inter-actions also occur.

Related literature

For dithio­phospho­rus compounds and their complexes, see: Heiduc et al. (2006 ▶); Karakuş et al. (2007 ▶); Gataulina et al. (2008 ▶). For the roles of dithio­phospho­rus compounds in agricultural, industrial and medicinal products such as additives to lubricant oils, solvent extraction reagents for metals, floatation agents for minerals, pesticides and insecticides, see: Thomas et al. (2001 ▶); Gray et al. (2003 ▶). For the synthetic routes reported for dithio­phospho­rus-type ligands, see: Alberti et al. (2007 ▶). For the preparation of ferrocenyl and aryl­dithio­phospho­nates and their complexes with a range of transition metals, see: Gray et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H16N+·C19H18O2PS2 −

M = 475.62

Orthorhombic,

a = 9.3782 (3) Å

b = 12.3467 (5) Å

c = 21.9651 (8) Å

V = 2543.33 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 294 K

0.52 × 0.36 × 0.32 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.862, T max = 0.912

43596 measured reflections

6343 independent reflections

5946 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.06

6343 reflections

289 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 2752 Friedel pairs

Flack parameter: −0.01 (6)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015820/xu5201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015820/xu5201Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015820/xu5201Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H16N+·C19H18O2PS2−	F(000) = 1016
Mr = 475.62	Dx = 1.242 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9895 reflections
a = 9.3782 (3) Å	θ = 2.7–28.4°
b = 12.3467 (5) Å	µ = 0.29 mm−1
c = 21.9651 (8) Å	T = 294 K
V = 2543.33 (16) Å3	Block, colorless
Z = 4	0.52 × 0.36 × 0.32 mm

Bruker Kappa APEXII CCD area-detector diffractometer	6343 independent reflections
Radiation source: fine-focus sealed tube	5946 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→12
Tmin = 0.862, Tmax = 0.912	k = −15→16
43596 measured reflections	l = −29→29

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0477P)2 + 1.2869P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
6343 reflections	Δρmax = 0.78 e Å−3
289 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 2752 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (6)

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.

	x	y	z	Uiso*/Ueq
S1	0.60412 (5)	0.18821 (4)	0.04905 (2)	0.02652 (11)
S2	0.57588 (5)	0.14708 (4)	0.19936 (2)	0.02634 (11)
P1	0.48082 (5)	0.18524 (4)	0.12180 (2)	0.01859 (10)
O1	0.34594 (14)	0.10520 (11)	0.11076 (6)	0.0211 (3)
O2	0.14963 (18)	0.59555 (13)	0.14733 (7)	0.0327 (3)
N1	−0.09897 (17)	0.20257 (14)	0.15241 (7)	0.0233 (3)
H1	−0.187 (3)	0.190 (2)	0.1517 (11)	0.029 (6)*
C1	0.38210 (18)	0.31092 (15)	0.12904 (8)	0.0192 (3)
C2	0.3729 (2)	0.36634 (17)	0.18402 (8)	0.0235 (4)
H2	0.4193	0.3392	0.2182	0.028*
C3	0.2957 (2)	0.46103 (17)	0.18858 (9)	0.0264 (4)
H3	0.2904	0.4972	0.2257	0.032*
C4	0.2256 (2)	0.50278 (16)	0.13774 (9)	0.0235 (4)
C5	0.2361 (2)	0.44975 (16)	0.08213 (9)	0.0229 (4)
H5	0.1911	0.4777	0.0478	0.027*
C6	0.3143 (2)	0.35486 (17)	0.07823 (8)	0.0222 (4)
H6	0.3217	0.3197	0.0409	0.027*
C7	0.0639 (3)	0.6348 (2)	0.09831 (11)	0.0393 (5)
H7A	0.0105	0.6967	0.1117	0.059*
H7B	−0.0007	0.5790	0.0854	0.059*
H7C	0.1241	0.6551	0.0649	0.059*
C8	0.3722 (2)	−0.00862 (16)	0.09988 (10)	0.0261 (4)
H8	0.4752	−0.0209	0.0970	0.031*
C9	0.3140 (3)	−0.07059 (18)	0.15388 (11)	0.0331 (5)
H9A	0.3298	−0.1467	0.1480	0.050*
H9B	0.2136	−0.0571	0.1576	0.050*
H9C	0.3617	−0.0473	0.1903	0.050*
C10	0.3016 (2)	−0.03846 (18)	0.03867 (10)	0.0291 (4)
C11	0.2350 (2)	0.04142 (18)	0.00213 (10)	0.0295 (4)
H11	0.2360	0.1134	0.0146	0.035*
C12	0.1688 (2)	0.01411 (19)	−0.05147 (11)	0.0322 (4)
H12	0.1235	0.0672	−0.0744	0.039*
C13	0.1694 (2)	−0.09410 (19)	−0.07195 (10)	0.0308 (4)
C14	0.1044 (2)	−0.1237 (2)	−0.12876 (11)	0.0358 (5)
H14	0.0577	−0.0718	−0.1521	0.043*
C15	0.1116 (3)	−0.2262 (2)	−0.14773 (11)	0.0381 (5)
H15	0.0704	−0.2448	−0.1848	0.046*
C16	0.1806 (3)	−0.3082 (2)	−0.11267 (11)	0.0406 (5)
H16	0.1840	−0.3790	−0.1270	0.049*
C17	0.2415 (3)	−0.28267 (19)	−0.05816 (11)	0.0363 (5)
H17	0.2852	−0.3362	−0.0350	0.044*
C18	0.2382 (2)	−0.17606 (17)	−0.03732 (9)	0.0264 (4)
C19	0.3031 (2)	−0.14337 (19)	0.01921 (10)	0.0301 (4)
H19	0.3475	−0.1955	0.0432	0.036*
C20	−0.0239 (2)	0.14297 (19)	0.10174 (10)	0.0304 (4)
H20A	0.0780	0.1436	0.1093	0.037*
H20B	−0.0410	0.1803	0.0636	0.037*
C21	−0.0742 (3)	0.0270 (2)	0.09624 (13)	0.0425 (6)
H21A	−0.0452	−0.0130	0.1316	0.064*
H21B	−0.0330	−0.0053	0.0606	0.064*
H21C	−0.1763	0.0256	0.0930	0.064*
C22	−0.0597 (2)	0.16311 (18)	0.21476 (9)	0.0292 (4)
H22B	−0.0739	0.0854	0.2164	0.035*
H22A	−0.1235	0.1960	0.2442	0.035*
C23	0.0930 (2)	0.1883 (2)	0.23275 (10)	0.0356 (5)
H23A	0.1128	0.1572	0.2719	0.053*
H23B	0.1060	0.2653	0.2346	0.053*
H23C	0.1569	0.1582	0.2031	0.053*
C24	−0.0782 (2)	0.32156 (17)	0.14353 (10)	0.0305 (4)
H24A	−0.1139	0.3416	0.1036	0.037*
H24B	0.0230	0.3375	0.1445	0.037*
C25	−0.1526 (3)	0.3895 (2)	0.19115 (12)	0.0438 (6)
H25A	−0.1499	0.4643	0.1792	0.066*
H25B	−0.1051	0.3810	0.2296	0.066*
H25C	−0.2500	0.3665	0.1949	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0237 (2)	0.0337 (2)	0.0222 (2)	0.0015 (2)	0.00873 (17)	0.0038 (2)
S2	0.0195 (2)	0.0391 (3)	0.0204 (2)	0.00257 (18)	−0.00307 (17)	0.0067 (2)
P1	0.01450 (18)	0.0253 (2)	0.01599 (19)	−0.00017 (17)	0.00075 (15)	0.00270 (18)
O1	0.0184 (6)	0.0224 (6)	0.0225 (6)	−0.0001 (5)	0.0014 (5)	−0.0009 (5)
O2	0.0394 (8)	0.0292 (8)	0.0294 (8)	0.0085 (6)	−0.0055 (6)	−0.0048 (6)
N1	0.0169 (7)	0.0286 (9)	0.0245 (8)	−0.0022 (6)	0.0012 (6)	0.0043 (6)
C1	0.0180 (7)	0.0228 (8)	0.0167 (8)	−0.0016 (7)	−0.0001 (6)	0.0010 (7)
C2	0.0263 (9)	0.0282 (10)	0.0161 (8)	−0.0030 (7)	−0.0046 (6)	0.0013 (7)
C3	0.0322 (10)	0.0281 (10)	0.0190 (9)	−0.0016 (8)	−0.0033 (7)	−0.0057 (7)
C4	0.0233 (9)	0.0222 (9)	0.0248 (10)	−0.0021 (7)	−0.0008 (7)	−0.0013 (7)
C5	0.0236 (9)	0.0276 (10)	0.0176 (9)	0.0016 (7)	−0.0029 (7)	0.0024 (7)
C6	0.0227 (8)	0.0288 (9)	0.0150 (8)	0.0007 (7)	0.0002 (6)	−0.0009 (7)
C7	0.0469 (14)	0.0349 (12)	0.0360 (12)	0.0139 (11)	−0.0034 (10)	0.0013 (10)
C8	0.0228 (9)	0.0237 (9)	0.0317 (10)	0.0011 (7)	0.0058 (8)	−0.0022 (8)
C9	0.0378 (12)	0.0277 (11)	0.0338 (11)	0.0008 (9)	0.0010 (9)	0.0060 (9)
C10	0.0249 (9)	0.0300 (10)	0.0325 (11)	−0.0059 (8)	0.0099 (8)	−0.0050 (9)
C11	0.0312 (10)	0.0282 (10)	0.0292 (11)	0.0023 (8)	0.0028 (8)	−0.0004 (8)
C12	0.0323 (10)	0.0318 (11)	0.0324 (11)	0.0051 (9)	0.0000 (9)	0.0051 (9)
C13	0.0269 (10)	0.0309 (11)	0.0346 (11)	0.0006 (8)	0.0049 (8)	0.0011 (9)
C14	0.0275 (10)	0.0462 (13)	0.0336 (11)	−0.0018 (9)	−0.0005 (9)	−0.0022 (10)
C15	0.0341 (11)	0.0497 (14)	0.0304 (11)	−0.0024 (10)	−0.0062 (9)	−0.0061 (10)
C16	0.0425 (13)	0.0359 (12)	0.0432 (13)	−0.0048 (11)	−0.0009 (10)	−0.0022 (11)
C17	0.0392 (12)	0.0289 (11)	0.0409 (13)	0.0010 (9)	−0.0019 (10)	−0.0011 (9)
C18	0.0200 (8)	0.0276 (10)	0.0316 (10)	−0.0024 (7)	0.0021 (7)	0.0047 (8)
C19	0.0261 (10)	0.0301 (10)	0.0341 (11)	0.0026 (8)	−0.0016 (8)	0.0056 (9)
C20	0.0208 (9)	0.0390 (11)	0.0315 (10)	−0.0016 (8)	0.0026 (7)	−0.0054 (9)
C21	0.0301 (11)	0.0376 (13)	0.0597 (16)	0.0023 (10)	−0.0012 (11)	−0.0117 (11)
C22	0.0237 (9)	0.0366 (12)	0.0271 (9)	−0.0038 (8)	−0.0005 (7)	0.0099 (8)
C23	0.0259 (10)	0.0507 (13)	0.0302 (10)	−0.0059 (10)	−0.0052 (8)	0.0083 (10)
C24	0.0340 (10)	0.0279 (10)	0.0295 (9)	−0.0025 (9)	0.0022 (8)	0.0040 (8)
C25	0.0553 (15)	0.0315 (12)	0.0445 (14)	0.0017 (11)	0.0031 (12)	−0.0052 (11)

S1—P1	1.9726 (6)	C11—H11	0.9300
S2—P1	1.9798 (6)	C12—C13	1.410 (3)
P1—O1	1.6234 (14)	C12—H12	0.9300
P1—C1	1.8140 (19)	C13—C14	1.436 (3)
O1—C8	1.447 (2)	C13—C18	1.421 (3)
O2—C4	1.365 (2)	C14—C15	1.335 (4)
O2—C7	1.429 (3)	C14—H14	0.9300
N1—C20	1.509 (3)	C15—C16	1.427 (4)
N1—C22	1.500 (2)	C15—H15	0.9300
N1—C24	1.495 (3)	C16—C17	1.364 (3)
N1—H1	0.84 (3)	C16—H16	0.9300
C1—C2	1.391 (3)	C17—C18	1.394 (3)
C2—C3	1.379 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.441 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C3	1.395 (3)	C20—H20A	0.9700
C4—C5	1.390 (3)	C20—H20B	0.9700
C5—C6	1.385 (3)	C21—C20	1.513 (3)
C5—H5	0.9300	C21—H21A	0.9600
C6—C1	1.395 (2)	C21—H21B	0.9600
C6—H6	0.9300	C21—H21C	0.9600
C7—H7A	0.9600	C22—C23	1.518 (3)
C7—H7B	0.9600	C22—H22A	0.9700
C7—H7C	0.9600	C22—H22B	0.9700
C8—C9	1.513 (3)	C23—H23A	0.9600
C8—C10	1.543 (3)	C23—H23B	0.9600
C8—H8	0.9800	C23—H23C	0.9600
C9—H9A	0.9600	C24—H24A	0.9700
C9—H9B	0.9600	C24—H24B	0.9700
C9—H9C	0.9600	C25—C24	1.512 (3)
C10—C11	1.417 (3)	C25—H25A	0.9600
C10—C19	1.364 (3)	C25—H25B	0.9600
C11—C12	1.373 (3)	C25—H25C	0.9600
S1—P1—S2	115.95 (3)	C13—C12—H12	119.8
O1—P1—S1	110.31 (5)	C12—C13—C14	121.1 (2)
O1—P1—S2	109.54 (5)	C12—C13—C18	120.4 (2)
O1—P1—C1	97.83 (8)	C18—C13—C14	118.5 (2)
C1—P1—S1	110.75 (6)	C13—C14—H14	120.3
C1—P1—S2	110.97 (6)	C15—C14—C13	119.4 (2)
C8—O1—P1	118.90 (12)	C15—C14—H14	120.3
C4—O2—C7	117.52 (17)	C14—C15—C16	121.8 (2)
C20—N1—H1	110.5 (18)	C14—C15—H15	119.1
C22—N1—C20	113.63 (17)	C16—C15—H15	119.1
C22—N1—H1	101.4 (17)	C15—C16—H16	120.0
C24—N1—C20	108.81 (16)	C17—C16—C15	120.0 (2)
C24—N1—C22	113.99 (16)	C17—C16—H16	120.0
C24—N1—H1	108.2 (18)	C16—C17—C18	119.8 (2)
C2—C1—P1	121.93 (14)	C16—C17—H17	120.1
C2—C1—C6	118.37 (17)	C18—C17—H17	120.1
C6—C1—P1	119.70 (14)	C13—C18—C19	117.0 (2)
C1—C2—H2	119.6	C17—C18—C13	120.5 (2)
C3—C2—C1	120.87 (17)	C17—C18—C19	122.5 (2)
C3—C2—H2	119.6	C10—C19—C18	122.1 (2)
C2—C3—C4	120.19 (18)	C10—C19—H19	118.9
C2—C3—H3	119.9	C18—C19—H19	118.9
C4—C3—H3	119.9	N1—C20—C21	112.04 (19)
O2—C4—C3	115.63 (17)	N1—C20—H20A	109.2
O2—C4—C5	124.61 (18)	N1—C20—H20B	109.2
C5—C4—C3	119.75 (18)	C21—C20—H20A	109.2
C4—C5—H5	120.3	C21—C20—H20B	109.2
C6—C5—C4	119.39 (17)	H20A—C20—H20B	107.9
C6—C5—H5	120.3	C20—C21—H21B	109.5
C1—C6—H6	119.3	C20—C21—H21C	109.5
C5—C6—C1	121.41 (17)	C20—C21—H21A	109.5
C5—C6—H6	119.3	H21B—C21—H21A	109.5
O2—C7—H7A	109.5	H21B—C21—H21C	109.5
O2—C7—H7B	109.5	H21C—C21—H21A	109.5
O2—C7—H7C	109.5	N1—C22—C23	113.76 (17)
H7A—C7—H7B	109.5	N1—C22—H22B	108.8
H7A—C7—H7C	109.5	N1—C22—H22A	108.8
H7B—C7—H7C	109.5	C23—C22—H22A	108.8
O1—C8—C9	107.47 (16)	C23—C22—H22B	108.8
O1—C8—C10	107.62 (16)	H22B—C22—H22A	107.7
O1—C8—H8	109.2	C22—C23—H23A	109.5
C9—C8—C10	114.04 (18)	C22—C23—H23B	109.5
C9—C8—H8	109.2	C22—C23—H23C	109.5
C10—C8—H8	109.2	H23A—C23—H23B	109.5
C8—C9—H9A	109.5	H23A—C23—H23C	109.5
C8—C9—H9B	109.5	H23B—C23—H23C	109.5
C8—C9—H9C	109.5	N1—C24—C25	113.29 (18)
H9A—C9—H9B	109.5	N1—C24—H24A	108.9
H9A—C9—H9C	109.5	N1—C24—H24B	108.9
H9B—C9—H9C	109.5	C25—C24—H24A	108.9
C11—C10—C8	121.10 (18)	C25—C24—H24B	108.9
C19—C10—C8	119.7 (2)	H24A—C24—H24B	107.7
C19—C10—C11	119.2 (2)	C24—C25—H25A	109.5
C10—C11—H11	119.5	C24—C25—H25B	109.5
C12—C11—C10	120.9 (2)	C24—C25—H25C	109.5
C12—C11—H11	119.5	H25A—C25—H25B	109.5
C11—C12—C13	120.3 (2)	H25A—C25—H25C	109.5
C11—C12—H12	119.8	H25B—C25—H25C	109.5
S1—P1—O1—C8	62.17 (14)	C5—C6—C1—P1	179.00 (15)
S2—P1—O1—C8	−66.62 (14)	C5—C6—C1—C2	−1.7 (3)
C1—P1—O1—C8	177.78 (14)	O1—C8—C10—C11	3.9 (2)
S1—P1—C1—C2	−133.20 (14)	O1—C8—C10—C19	−176.08 (17)
S1—P1—C1—C6	46.06 (16)	C9—C8—C10—C11	123.0 (2)
S2—P1—C1—C2	−2.94 (17)	C9—C8—C10—C19	−57.0 (3)
S2—P1—C1—C6	176.32 (13)	C8—C10—C11—C12	−178.18 (19)
O1—P1—C1—C2	111.53 (16)	C19—C10—C11—C12	1.8 (3)
O1—P1—C1—C6	−69.20 (16)	C8—C10—C19—C18	179.61 (18)
P1—O1—C8—C9	113.03 (16)	C11—C10—C19—C18	−0.4 (3)
P1—O1—C8—C10	−123.74 (14)	C10—C11—C12—C13	−1.7 (3)
C7—O2—C4—C3	−173.5 (2)	C11—C12—C13—C14	−178.2 (2)
C7—O2—C4—C5	6.5 (3)	C11—C12—C13—C18	0.1 (3)
C22—N1—C20—C21	68.7 (2)	C12—C13—C14—C15	177.6 (2)
C24—N1—C20—C21	−163.15 (19)	C18—C13—C14—C15	−0.7 (3)
C20—N1—C22—C23	68.3 (2)	C12—C13—C18—C17	−178.6 (2)
C24—N1—C22—C23	−57.1 (2)	C12—C13—C18—C19	1.2 (3)
C20—N1—C24—C25	178.55 (19)	C14—C13—C18—C17	−0.3 (3)
C22—N1—C24—C25	−53.5 (2)	C14—C13—C18—C19	179.57 (19)
P1—C1—C2—C3	−179.18 (16)	C13—C14—C15—C16	0.9 (4)
C6—C1—C2—C3	1.6 (3)	C14—C15—C16—C17	0.0 (4)
C1—C2—C3—C4	−0.1 (3)	C15—C16—C17—C18	−1.0 (4)
O2—C4—C3—C2	178.63 (18)	C16—C17—C18—C13	1.2 (3)
C5—C4—C3—C2	−1.3 (3)	C16—C17—C18—C19	−178.7 (2)
O2—C4—C5—C6	−178.79 (19)	C13—C18—C19—C10	−1.1 (3)
C3—C4—C5—C6	1.1 (3)	C17—C18—C19—C10	178.7 (2)
C4—C5—C6—C1	0.4 (3)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C13/C18/C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2i	0.84 (3)	2.52 (3)	3.2911 (17)	154 (2)
C20—H20A···O1	0.97	2.56	3.505 (2)	166
C7—H7B···Cg2ii	0.96	2.90	3.6578 (28)	137
C24—H24B···Cg1iii	0.97	2.79	3.7496 (24)	171

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C13/C18/C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2i	0.84 (3)	2.52 (3)	3.2911 (17)	154 (2)
C20—H20A⋯O1	0.97	2.56	3.505 (2)	166
C7—H7B⋯Cg2ii	0.96	2.90	3.658 (3)	137
C24—H24B⋯Cg1iii	0.97	2.79	3.750 (2)	171

Symmetry codes: (i) ; (ii) ; (iii) .