S-[2-(2,2-Di­methyl­propanamido)-3-(tri­fluoro­meth­yl)phen­yl] N,N-diiso­propyl­dithio­carbamate

El-Hiti, G.A.; Smith, K.; Hegazy, A.S.; Alshammari, M.B.; Kariuki, B.M.

doi:10.1107/S2414314618000299

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x180029

https://doi.org/10.1107/S2414314618000299

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S-[2-(2,2-Dimethylpropanamido)-3-(trifluoromethyl)phenyl] N,N-diisopropyldithiocarbamate

Gamal A. El-Hiti,^a ^* Keith Smith,^b Amany S. Hegazy,^b Mohammed B. Alshammari ^c and Benson M. Kariuki ^b ‡

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK, and ^cChemistry Department, College of Sciences and Humanities, Prince Sattam bin Abdulaziz University, PO Box 83, Al-Kharij 11942, Saudi Arabia
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 4 January 2018; accepted 5 January 2018; online 12 January 2018)

In the title compound, C₁₉H₂₇F₃N₂OS₂, the dihedral angle between the benzene ring and dithiocarbamate group is 67.00 (9)° and a weak intramolecular N—H⋯S interaction generates an S(7) ring. The tert-butyl group is disordered over two orientations in a 0.628 (14):0.372 (14) ratio. In the crystal, inversion dimers linked by pairs of weak C—H⋯O interactions generate R₂²(20) loops and the aromatic rings of neighbouring pairs of molecules are involved in very weak π–π stacking interactions [centroid–centroid separation = 4.0042 (13) Å].

Keywords: crystal structure; intramolecular N—H⋯S interaction.

CCDC reference: 1814851

Structure description

Various N-(substituted phenyl)pivalamides can be substituted efficiently in reactions with lithium reagents followed by reaction with electrophiles (e.g.: Smith et al., 2015 ; Smith et al., 2012 ). Recently, the X-ray crystal structure of 4-(pivaloylamino)pyridin-3-yl N,N-diisopropyldithiocarbamate has been published (El-Hiti et al., 2014 ). We now describe the synthesis and structure of the title compound (Fig. 1).

Figure 1
The molecular structure, with displacement ellipsoids at the 50% probability level, showing both orientations of the disordered tert-butyl group.

An intramolecular N1—H1⋯S2 contact is observed (Table 1). The crystal packing is shown in Fig. 2 and features inversion dimers linked by weak C—H⋯O interactions and very weak aromatic π–π stacking interactions [centroid–centroid separation = 4.0042 (13) Å].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2	0.86	2.65	3.2576 (18)	129
C14—H14⋯O1ⁱ	0.98	2.35	3.097 (4)	132
Symmetry code: (i) -x+1, -y+1, -z+1.

Figure 2
Crystal packing, viewed down [100]. Hydrogen atoms have been omitted for clarity.

Synthesis and crystallization

N-(2-(trifluoromethyl)phenyl)pivalamide and n-butylltihium (two equivalents) in anhydrous tetrahydrofuran at 0°C was reacted with tetraisopropylthiuram disulfide (one equivalent). Crystallization of the crude product using ethyl acetate as solvent gave colourless blocks, m.p. 129–131°C.

The NMR spectrum indicates that the two iso-propyl groups are different, possibly due to restricted rotation about the N—C bond (Chatgilialoglu & Asmus, 1990 ). The NMR assignments are based on predicted chemical shifts and coupling patterns and have not been rigorously confirmed. ¹H NMR (500 MHz, CDCl₃): δ 7.84 (d, J = 7.8 Hz, 1 H, H-6), 7.74 (d, J = 7.8 Hz, 1 H, H-4), 7.72 (br s, exch., 1 H, NH), 7.48 (app. t, J = 7.8 Hz, 1 H, H-5), 4.99, 4.07 [2 br, 2 H, 2 CH(CH₃)₂], 1.66, 1.41 [2 br, 12 H, 2 CH(CH₃)₂], 1.31 [s, 9 H, C(CH₃)₃]; ¹³C NMR (125 MHz, CDCl₃): δ 192.4 (C=S), 177.8 (C=O), 140.6 (C-6), 140.5 (C-1), 133.6 (m, C-2), 130.4 (q, J = 30.1 Hz, C-3), 129.2 (q, J = 5.0 Hz, C-4), 128.1 (C-5), 123.2 (q, J = 274.0 Hz, CF₃), 56.5, 52.7 [2 CH(CH₃)₂], 39.1 [C(CH₃)₃], 27.4 [C(CH₃)₃], 20.2, 19.6 [2 CH(CH₃)₂]; EI–MS: m/z (%) = 420 (M⁺, 12), 259 (31), 244 (72), 219 (23), 144 (80), 102 (100), 100 (41), 57 (26); HRMS (EI): calculated for C₁₉H₂₇F₃N₂OS₂ (MH⁺): 420.1517; found: 420.1512.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The tert-butyl group is disordered and was modelled with two components with occupancies of 0.628 (14)/0.372 (14).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₂₇F₃N₂OS₂
M_r	420.54
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	10.0633 (3), 11.5253 (4), 11.8648 (3)
α, β, γ (°)	103.597 (2), 112.018 (3), 109.899 (3)
V (Å³)	1090.81 (6)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	2.53
Crystal size (mm)	0.36 × 0.21 × 0.20

Data collection
Diffractometer	Agilent SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.874, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	17158, 4349, 3933
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.135, 1.08
No. of reflections	4349
No. of parameters	282
No. of restraints	72
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.52
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS2013 (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1814851

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618000299/hb4200sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618000299/hb4200Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618000299/hb4200Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

S-[2-(2,2-Dimethylpropanamido)-3-(trifluoromethyl)phenyl] N,N-diisopropyldithiocarbamate top

Crystal data top

C₁₉H₂₇F₃N₂OS₂	Z = 2
M_r = 420.54	F(000) = 444
Triclinic, P1	D_x = 1.280 Mg m⁻³
a = 10.0633 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.5253 (4) Å	Cell parameters from 12098 reflections
c = 11.8648 (3) Å	θ = 4.4–74.0°
α = 103.597 (2)°	µ = 2.53 mm⁻¹
β = 112.018 (3)°	T = 296 K
γ = 109.899 (3)°	Block, colourless
V = 1090.81 (6) Å³	0.36 × 0.21 × 0.20 mm

Data collection top

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	3933 reflections with I > 2σ(I)
ω scans	R_int = 0.022
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	θ_max = 74.0°, θ_min = 4.4°
T_min = 0.874, T_max = 0.917	h = −12→12
17158 measured reflections	k = −13→14
4349 independent reflections	l = −14→14

Refinement top

Refinement on F²	72 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0682P)² + 0.462P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4349 reflections	Δρ_max = 0.70 e Å⁻³
282 parameters	Δρ_min = −0.52 e Å⁻³

Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) numerical absorption correction based on gaussian integration over a multifaceted crystal model empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times U_eq(C), and were allowed to spin about the C—C bond. The N—H bond was fixed at 0.86 Å and aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the U_eq for the atoms to which they are bonded.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5618 (2)	0.1992 (2)	0.6694 (2)	0.0492 (5)
C2	0.4617 (2)	0.23679 (19)	0.58578 (18)	0.0436 (4)
C3	0.4637 (2)	0.2317 (2)	0.46719 (19)	0.0458 (4)
C4	0.5665 (3)	0.1937 (2)	0.4360 (2)	0.0550 (5)
H4	0.5669	0.1905	0.3570	0.066*
C5	0.6685 (3)	0.1604 (2)	0.5223 (2)	0.0613 (6)
H5	0.7390	0.1365	0.5022	0.074*
C6	0.6659 (3)	0.1627 (2)	0.6372 (2)	0.0584 (5)
H6	0.7342	0.1396	0.6945	0.070*
C7	0.5636 (3)	0.1943 (3)	0.7954 (3)	0.0671 (6)
C8	0.4096 (2)	0.3958 (2)	0.7162 (2)	0.0482 (4)
C9	0.2774 (3)	0.4292 (3)	0.7235 (2)	0.0596 (6)
C10	0.3551 (12)	0.5554 (10)	0.8486 (7)	0.121 (3)	0.628 (14)
H10A	0.3875	0.5347	0.9252	0.181*	0.628 (14)
H10B	0.2782	0.5882	0.8444	0.181*	0.628 (14)
H10C	0.4491	0.6239	0.8561	0.181*	0.628 (14)
C11	0.1496 (12)	0.3079 (9)	0.7222 (14)	0.115 (3)	0.628 (14)
H11A	0.2034	0.2724	0.7790	0.172*	0.628 (14)
H11B	0.0788	0.2386	0.6326	0.172*	0.628 (14)
H11C	0.0867	0.3369	0.7542	0.172*	0.628 (14)
C12	0.1958 (10)	0.4518 (9)	0.5999 (6)	0.080 (2)	0.628 (14)
H12A	0.1168	0.4785	0.6048	0.121*	0.628 (14)
H12B	0.1424	0.3692	0.5214	0.121*	0.628 (14)
H12C	0.2765	0.5219	0.5954	0.121*	0.628 (14)
C10A	0.3656 (18)	0.5855 (7)	0.8072 (15)	0.095 (4)	0.372 (14)
H10D	0.3964	0.6315	0.7563	0.143*	0.372 (14)
H10E	0.4612	0.6105	0.8883	0.143*	0.372 (14)
H10F	0.2935	0.6107	0.8285	0.143*	0.372 (14)
C11A	0.2190 (19)	0.3623 (14)	0.8041 (16)	0.093 (3)	0.372 (14)
H11D	0.1357	0.3818	0.8098	0.140*	0.372 (14)
H11E	0.3089	0.3970	0.8924	0.140*	0.372 (14)
H11F	0.1757	0.2660	0.7609	0.140*	0.372 (14)
C12A	0.1355 (17)	0.391 (2)	0.5898 (8)	0.113 (5)	0.372 (14)
H12D	0.0662	0.2941	0.5481	0.169*	0.372 (14)
H12E	0.1759	0.4174	0.5335	0.169*	0.372 (14)
H12F	0.0746	0.4357	0.6030	0.169*	0.372 (14)
C13	0.1484 (2)	0.1780 (2)	0.28142 (18)	0.0441 (4)
C14	0.1219 (3)	0.3324 (2)	0.1703 (2)	0.0508 (5)
H14	0.2404	0.3683	0.2152	0.061*
C15	0.0900 (4)	0.4433 (3)	0.2300 (3)	0.0743 (7)
H15A	−0.0252	0.4126	0.1868	0.111*
H15B	0.1432	0.5219	0.2176	0.111*
H15C	0.1316	0.4660	0.3239	0.111*
C16	0.0630 (4)	0.2946 (3)	0.0227 (3)	0.0744 (7)
H16A	0.0758	0.2179	−0.0136	0.112*
H16B	0.1258	0.3700	0.0111	0.112*
H16C	−0.0499	0.2718	−0.0229	0.112*
C17	−0.1287 (2)	0.1370 (2)	0.1281 (2)	0.0564 (5)
H17	−0.1658	0.1857	0.0767	0.068*
C18	−0.1937 (3)	0.1447 (3)	0.2245 (3)	0.0773 (7)
H18A	−0.1688	0.0922	0.2731	0.116*
H18B	−0.3096	0.1093	0.1754	0.116*
H18C	−0.1438	0.2376	0.2859	0.116*
C19	−0.2022 (3)	−0.0068 (3)	0.0255 (3)	0.0786 (8)
H19A	−0.1534	−0.0057	−0.0302	0.118*
H19B	−0.3176	−0.0423	−0.0287	0.118*
H19C	−0.1821	−0.0630	0.0708	0.118*
N1	0.3565 (2)	0.27758 (18)	0.61456 (16)	0.0489 (4)
H1	0.2532	0.2247	0.5651	0.059*
N2	0.05355 (19)	0.21183 (17)	0.19727 (16)	0.0458 (4)
O1	0.55330 (19)	0.46862 (17)	0.79613 (18)	0.0683 (5)
F1	0.4313 (3)	0.1794 (3)	0.8007 (2)	0.1186 (8)
F2	0.6854 (3)	0.30527 (19)	0.90418 (15)	0.0974 (6)
F3	0.5919 (3)	0.09416 (18)	0.81723 (17)	0.0949 (6)
S1	0.36197 (6)	0.29820 (5)	0.36548 (5)	0.05110 (16)
S2	0.08666 (7)	0.04280 (5)	0.31403 (6)	0.05922 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (10)	0.0475 (10)	0.0471 (10)	0.0224 (8)	0.0137 (8)	0.0191 (8)
C2	0.0377 (9)	0.0446 (10)	0.0429 (9)	0.0205 (8)	0.0156 (7)	0.0158 (8)
C3	0.0396 (9)	0.0498 (10)	0.0429 (9)	0.0220 (8)	0.0163 (8)	0.0175 (8)
C4	0.0504 (11)	0.0603 (12)	0.0523 (11)	0.0289 (10)	0.0254 (9)	0.0168 (9)
C5	0.0500 (11)	0.0609 (13)	0.0695 (14)	0.0345 (10)	0.0259 (11)	0.0162 (11)
C6	0.0469 (11)	0.0541 (12)	0.0616 (13)	0.0289 (10)	0.0135 (10)	0.0201 (10)
C7	0.0670 (15)	0.0782 (16)	0.0636 (14)	0.0414 (13)	0.0255 (12)	0.0422 (13)
C8	0.0490 (11)	0.0556 (11)	0.0501 (10)	0.0288 (9)	0.0276 (9)	0.0268 (9)
C9	0.0616 (13)	0.0820 (16)	0.0579 (12)	0.0466 (12)	0.0374 (11)	0.0327 (12)
C10	0.105 (5)	0.167 (6)	0.072 (4)	0.092 (5)	0.033 (3)	−0.001 (4)
C11	0.101 (5)	0.152 (6)	0.173 (8)	0.079 (5)	0.107 (6)	0.099 (6)
C12	0.085 (4)	0.118 (5)	0.081 (3)	0.080 (4)	0.045 (3)	0.052 (3)
C10A	0.108 (6)	0.100 (6)	0.122 (8)	0.071 (5)	0.080 (7)	0.042 (5)
C11A	0.100 (7)	0.132 (7)	0.119 (7)	0.073 (5)	0.089 (6)	0.077 (6)
C12A	0.095 (8)	0.183 (12)	0.078 (6)	0.093 (8)	0.045 (5)	0.038 (7)
C13	0.0421 (9)	0.0462 (10)	0.0400 (9)	0.0224 (8)	0.0174 (8)	0.0148 (8)
C14	0.0446 (10)	0.0562 (11)	0.0546 (11)	0.0258 (9)	0.0217 (9)	0.0297 (9)
C15	0.0895 (19)	0.0542 (13)	0.0849 (18)	0.0357 (13)	0.0461 (16)	0.0308 (13)
C16	0.0861 (18)	0.0880 (18)	0.0624 (14)	0.0449 (16)	0.0399 (14)	0.0415 (14)
C17	0.0386 (10)	0.0569 (12)	0.0615 (12)	0.0209 (9)	0.0148 (9)	0.0256 (10)
C18	0.0533 (13)	0.0873 (19)	0.099 (2)	0.0336 (13)	0.0424 (14)	0.0440 (16)
C19	0.0589 (14)	0.0589 (14)	0.0694 (16)	0.0187 (12)	0.0026 (12)	0.0150 (12)
N1	0.0385 (8)	0.0600 (10)	0.0445 (8)	0.0250 (7)	0.0181 (7)	0.0179 (7)
N2	0.0384 (8)	0.0483 (9)	0.0467 (8)	0.0215 (7)	0.0163 (7)	0.0203 (7)
O1	0.0495 (9)	0.0578 (9)	0.0769 (11)	0.0219 (7)	0.0263 (8)	0.0105 (8)
F1	0.1074 (14)	0.208 (2)	0.1278 (16)	0.0988 (16)	0.0815 (13)	0.1291 (18)
F2	0.1329 (16)	0.0901 (12)	0.0533 (8)	0.0560 (12)	0.0331 (10)	0.0231 (8)
F3	0.1371 (16)	0.0857 (11)	0.0758 (10)	0.0685 (11)	0.0409 (10)	0.0520 (9)
S1	0.0404 (3)	0.0597 (3)	0.0505 (3)	0.0226 (2)	0.0177 (2)	0.0290 (2)
S2	0.0527 (3)	0.0490 (3)	0.0594 (3)	0.0190 (2)	0.0150 (2)	0.0265 (2)

Geometric parameters (Å, º) top

C1—C2	1.392 (3)	C10A—H10D	0.9600
C1—C6	1.394 (3)	C10A—H10E	0.9600
C1—C7	1.503 (3)	C10A—H10F	0.9600
C2—C3	1.402 (3)	C11A—H11D	0.9600
C2—N1	1.411 (3)	C11A—H11E	0.9600
C3—C4	1.385 (3)	C11A—H11F	0.9600
C3—S1	1.770 (2)	C12A—H12D	0.9600
C4—C5	1.384 (3)	C12A—H12E	0.9600
C4—H4	0.9300	C12A—H12F	0.9600
C5—C6	1.368 (4)	C13—N2	1.335 (2)
C5—H5	0.9300	C13—S2	1.664 (2)
C6—H6	0.9300	C13—S1	1.803 (2)
C7—F1	1.310 (3)	C14—N2	1.493 (3)
C7—F2	1.332 (3)	C14—C15	1.504 (4)
C7—F3	1.337 (3)	C14—C16	1.515 (3)
C8—O1	1.211 (3)	C14—H14	0.9800
C8—N1	1.359 (3)	C15—H15A	0.9600
C8—C9	1.532 (3)	C15—H15B	0.9600
C9—C10	1.507 (6)	C15—H15C	0.9600
C9—C12A	1.513 (7)	C16—H16A	0.9600
C9—C11A	1.520 (7)	C16—H16B	0.9600
C9—C12	1.522 (5)	C16—H16C	0.9600
C9—C11	1.536 (6)	C17—N2	1.498 (2)
C9—C10A	1.558 (7)	C17—C18	1.515 (4)
C10—H10A	0.9600	C17—C19	1.522 (4)
C10—H10B	0.9600	C17—H17	0.9800
C10—H10C	0.9600	C18—H18A	0.9600
C11—H11A	0.9600	C18—H18B	0.9600
C11—H11B	0.9600	C18—H18C	0.9600
C11—H11C	0.9600	C19—H19A	0.9600
C12—H12A	0.9600	C19—H19B	0.9600
C12—H12B	0.9600	C19—H19C	0.9600
C12—H12C	0.9600	N1—H1	0.8600

C2—C1—C6	120.0 (2)	H10D—C10A—H10F	109.5
C2—C1—C7	123.1 (2)	H10E—C10A—H10F	109.5
C6—C1—C7	116.90 (19)	C9—C11A—H11D	109.5
C1—C2—C3	118.57 (18)	C9—C11A—H11E	109.5
C1—C2—N1	122.61 (18)	H11D—C11A—H11E	109.5
C3—C2—N1	118.80 (17)	C9—C11A—H11F	109.5
C4—C3—C2	120.60 (19)	H11D—C11A—H11F	109.5
C4—C3—S1	116.70 (16)	H11E—C11A—H11F	109.5
C2—C3—S1	121.95 (15)	C9—C12A—H12D	109.5
C5—C4—C3	119.9 (2)	C9—C12A—H12E	109.5
C5—C4—H4	120.0	H12D—C12A—H12E	109.5
C3—C4—H4	120.0	C9—C12A—H12F	109.5
C6—C5—C4	120.1 (2)	H12D—C12A—H12F	109.5
C6—C5—H5	120.0	H12E—C12A—H12F	109.5
C4—C5—H5	120.0	N2—C13—S2	126.48 (15)
C5—C6—C1	120.7 (2)	N2—C13—S1	113.18 (14)
C5—C6—H6	119.6	S2—C13—S1	120.33 (11)
C1—C6—H6	119.6	N2—C14—C15	111.50 (19)
F1—C7—F2	105.7 (3)	N2—C14—C16	112.07 (19)
F1—C7—F3	107.3 (2)	C15—C14—C16	112.0 (2)
F2—C7—F3	103.7 (2)	N2—C14—H14	107.0
F1—C7—C1	115.9 (2)	C15—C14—H14	107.0
F2—C7—C1	112.5 (2)	C16—C14—H14	107.0
F3—C7—C1	110.9 (2)	C14—C15—H15A	109.5
O1—C8—N1	121.13 (19)	C14—C15—H15B	109.5
O1—C8—C9	122.8 (2)	H15A—C15—H15B	109.5
N1—C8—C9	116.04 (18)	C14—C15—H15C	109.5
C12A—C9—C11A	111.0 (6)	H15A—C15—H15C	109.5
C10—C9—C12	110.6 (5)	H15B—C15—H15C	109.5
C10—C9—C8	109.1 (4)	C14—C16—H16A	109.5
C12A—C9—C8	115.1 (6)	C14—C16—H16B	109.5
C11A—C9—C8	108.0 (5)	H16A—C16—H16B	109.5
C12—C9—C8	107.8 (3)	C14—C16—H16C	109.5
C10—C9—C11	111.3 (4)	H16A—C16—H16C	109.5
C12—C9—C11	108.8 (4)	H16B—C16—H16C	109.5
C8—C9—C11	109.1 (3)	N2—C17—C18	112.87 (19)
C12A—C9—C10A	109.8 (6)	N2—C17—C19	113.3 (2)
C11A—C9—C10A	107.0 (5)	C18—C17—C19	113.3 (2)
C8—C9—C10A	105.5 (6)	N2—C17—H17	105.5
C9—C10—H10A	109.5	C18—C17—H17	105.5
C9—C10—H10B	109.5	C19—C17—H17	105.5
H10A—C10—H10B	109.5	C17—C18—H18A	109.5
C9—C10—H10C	109.5	C17—C18—H18B	109.5
H10A—C10—H10C	109.5	H18A—C18—H18B	109.5
H10B—C10—H10C	109.5	C17—C18—H18C	109.5
C9—C11—H11A	109.5	H18A—C18—H18C	109.5
C9—C11—H11B	109.5	H18B—C18—H18C	109.5
H11A—C11—H11B	109.5	C17—C19—H19A	109.5
C9—C11—H11C	109.5	C17—C19—H19B	109.5
H11A—C11—H11C	109.5	H19A—C19—H19B	109.5
H11B—C11—H11C	109.5	C17—C19—H19C	109.5
C9—C12—H12A	109.5	H19A—C19—H19C	109.5
C9—C12—H12B	109.5	H19B—C19—H19C	109.5
H12A—C12—H12B	109.5	C8—N1—C2	123.57 (17)
C9—C12—H12C	109.5	C8—N1—H1	118.2
H12A—C12—H12C	109.5	C2—N1—H1	118.2
H12B—C12—H12C	109.5	C13—N2—C14	122.25 (16)
C9—C10A—H10D	109.5	C13—N2—C17	123.01 (17)
C9—C10A—H10E	109.5	C14—N2—C17	114.67 (16)
H10D—C10A—H10E	109.5	C3—S1—C13	105.47 (9)
C9—C10A—H10F	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.86	2.65	3.2576 (18)	129
C14—H14···O1ⁱ	0.98	2.35	3.097 (4)	132

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

‡Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.

Funding information

The project was supported by King Saud University, Deanship of Scientific Research, Research Chairs. We thank the EPSRC for the grant which supplied the MS instrumentation used in this study.

References

Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA. Google Scholar
Chatgilialoglu, C. & Asmus, K.-D. (1990). Sulfur-Centered Reactive Intermediates in Chemistry and Biology. Vol. 179, NATO–ASI Series. New York and London: Plenum. Google Scholar
El-Hiti, G. A., Smith, K., Hegazy, A. S., Baashen, M. & Kariuki, B. M. (2014). Acta Cryst. E70, o1069–o1070. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Smith, K., El-Hiti, G. A. & Alshammari, M. B. (2012). J. Org. Chem. 77, 11210–11215. Web of Science CrossRef CAS PubMed Google Scholar
Smith, K., El-Hiti, G. A., Hegazy, A. S., Alshammari, M. B. & Masmali, A. M. (2015). ARKIVOC iv, 19–47. Google Scholar

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