(1Z,2E)-1-(3,4-Diphenyl-2,3-di­hydro-1,3-thia­zol-2-yl­idene)-2-(1-p-tolyl­ethyl­idene)hydrazine

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Hassan, A.A.; Albayati, M.R.

doi:10.1107/S1600536813020254

(1Z,2E)-1-(3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene)-2-(1-p-tolylethylidene)hydrazine

S. K. Mohamed, J. T. Mague, M. Akkurt, A. A. Hassan and M. R. Albayati

In the title compound, C₂₄H₂₁N₃S, the thiazole ring makes dihedral angles of 52.03 (6), 62.63 (6) and 12.35 (6)°, respectively, with the two phenyl rings and the benzene ring. In the crystal, weak C—H

π interactions occur between inversion-related molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813020254/xu5722sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813020254/xu5722Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813020254/xu5722Isup3.cml Supplementary material

CCDC reference: 961836

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.119
Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B   ..  S1      ..       3.03 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ? Do !
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         34
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          ! Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

1,3-Thiazole containing compounds are a great class of sulfur heterocyclic molecules due to their vital interest in pharmaceutical and industrial chemistry. Numerous of synthesized active thiazole scaffold molecules having diverse of biologically activities have been reported (Ramla et al., 2006; Popsavin et al., 2007; Kumar et al., 2007; Pandeya et al., 1999; Narayana et al., 2004; Shiradkar et al., 2007; Amin et al., 2008; Shih & Ying, 2004; Andreani et al., 1987). In addition, thiazole compounds have not only found in natural molecules such as Thiamin (vitamin B1) but also have been found in many drugs such as Abafungin (antifungal drug), Bleomycine and Tiazofurin (antineoplastic drug), Ritonavir (antiretroviral drug) and Sulfathiazol (antimicrobial drug) (Siddiqui et al., 2009).

In the title compound (I), (Fig. 1), the (S1/N1/C1–C3) thiazole ring is essentially planar with a maximum deviation of -0.006 (1) Å for C2. The dihedral angles between the thiazole ring, and the phenyl rings (C4–C9 and C10–C15) and the benzene ring (C18—C23) are 52.03 (6), 62.63 (6) and 12.35 (6)°, respectively.

In the crystal structure, the title molecules pack in a layer structure with the layers approximately parallel to [101] and held together by a combination of C—H···S hydrogen bonds (Table 1 and Fig. 2) and C—H···π interactions (Fig. 3: H15···Cg1 = 2.71 Å; C15—H15···Cg1 = 160° and H16a···Cg2 = 2.77 Å; C16—H16a···Cg2 = 143° where Cg1 is the centroid of the ring C18–C23 at 1 - x, 1 - y, 1 - z and Cg2 is the centroid of the ring C18–C23 at 2 - x, 1 - y, 1 - z).

Related literature top

For the syntheses and bioactivity of thiazole-containing compounds, see: Siddiqui et al. (2009); Ramla et al. (2006); Popsavin et al. (2007); Kumar et al. (2007); Pandeya et al. (1999); Narayana et al. (2004); Shiradkar et al. (2007); Amin et al. (2008); Shih & Ying (2004); Andreani et al. (1987).

Experimental top

A solution of 283 mg (1 mmol) (2E)-2-[1-(4-methylphenyl)ethylidene]-N-phenylhydrazinecarbothioamide in 15 ml e thanol was added dropwise to a solution of 199 mg (1 mmol) 2-bromo-1-phenylethanone in 20 ml e thanol and few drops of piperidine. The reaction mixture was stirred and refluxed for 6 h. On cooling the solid product was precipitated, filtered off and recrystallized from ethanol to furnish translucent yellow blocks (M.p. 509 - 511 K) suitable for X-ray diffraction.

IR [ν, cm^-1,KBr]: 3052 (Ar—CH), 2941, 2863 (Ali – CH), 1594 (Ar—C=C), 1350(C=S); ¹H– NMR [δ, p.p.m., CDCl₃]: 1.26, 1.65, 1.94 and 2.20 (10H, cyclohexane – CH₂), 7.707,7.51, 7.55 (SH, Ar –H); ¹³C–NMR [δ, p.p.m., CDCl₃]: 23.58, 24.52 and 33.90 (cyclohexane- CH₂), 112.19 (spiro Cx b), 127.81, 129.87, 130.22 (Ar- CH), 135.07 (Ar-c), 187.83 (C=S).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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, 2012) and DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. Closeup view (down b) of the C—H···π interactions.

(1Z,2E)-1-(3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene)-2-(1-p-tolylethylidene)hydrazine top

Crystal data top

C₂₄H₂₁N₃S	Z = 2
M_r = 383.51	F(000) = 404
Triclinic, P1	D_x = 1.273 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9370 (8) Å	Cell parameters from 9946 reflections
b = 10.7587 (11) Å	θ = 2.5–29.1°
c = 11.9325 (13) Å	µ = 0.18 mm⁻¹
α = 94.922 (2)°	T = 150 K
β = 97.436 (2)°	Block, translucent yellow
γ = 95.383 (2)°	0.30 × 0.15 × 0.12 mm
V = 1000.95 (18) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	4870 independent reflections
Radiation source: fine-focus sealed tube	4287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 28.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −10→10
T_min = 0.83, T_max = 0.98	k = −14→13
17908 measured reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.119	W = 1/[Σ²(FO²) + (0.0663P)² + 0.2395P] WHERE P = (FO² + 2FC²)/3
S = 1.06	(Δ/σ)_max < 0.001
4870 reflections	Δρ_max = 0.33 e Å⁻³
255 parameters	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₂₁N₃S	γ = 95.383 (2)°
M_r = 383.51	V = 1000.95 (18) Å³
Triclinic, P1	Z = 2
a = 7.9370 (8) Å	Mo Kα radiation
b = 10.7587 (11) Å	µ = 0.18 mm⁻¹
c = 11.9325 (13) Å	T = 150 K
α = 94.922 (2)°	0.30 × 0.15 × 0.12 mm
β = 97.436 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	4870 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	4287 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.98	R_int = 0.034
17908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
4870 reflections	Δρ_min = −0.30 e Å⁻³
255 parameters

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at ϕ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in ϕ, collected at ω = -30.00 and 210.00°. The scan time was 20 sec/frame.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.39566 (4)	0.41513 (3)	0.16060 (3)	0.0296 (1)
N1	0.40562 (13)	0.65478 (10)	0.15561 (9)	0.0266 (3)
N2	0.58080 (15)	0.59963 (11)	0.31261 (10)	0.0320 (3)
N3	0.63650 (14)	0.49413 (11)	0.36084 (9)	0.0304 (3)
C1	0.27238 (16)	0.47641 (12)	0.05087 (11)	0.0294 (3)
C2	0.28971 (15)	0.60194 (12)	0.06040 (10)	0.0250 (3)
C3	0.47515 (15)	0.56729 (12)	0.22097 (10)	0.0269 (3)
C4	0.18436 (15)	0.68175 (12)	−0.00790 (10)	0.0250 (3)
C5	0.16266 (16)	0.66568 (13)	−0.12623 (11)	0.0299 (4)
C6	0.05372 (18)	0.73637 (14)	−0.18849 (12)	0.0353 (4)
C7	−0.03595 (18)	0.82156 (13)	−0.13387 (13)	0.0371 (4)
C8	−0.01560 (18)	0.83778 (13)	−0.01614 (13)	0.0354 (4)
C9	0.09520 (17)	0.76964 (12)	0.04655 (11)	0.0298 (3)
C10	0.46544 (15)	0.78546 (12)	0.17887 (11)	0.0268 (3)
C11	0.54876 (16)	0.84599 (12)	0.10073 (11)	0.0296 (4)
C12	0.60307 (18)	0.97346 (14)	0.12303 (12)	0.0357 (4)
C13	0.5727 (2)	1.03903 (14)	0.22148 (14)	0.0417 (5)
C14	0.4910 (2)	0.97690 (16)	0.30020 (14)	0.0445 (5)
C15	0.43855 (18)	0.84986 (14)	0.27966 (12)	0.0361 (4)
C16	0.72732 (18)	0.64349 (13)	0.53188 (11)	0.0338 (4)
C17	0.70933 (16)	0.51734 (13)	0.46504 (11)	0.0281 (3)
C18	0.78315 (15)	0.41138 (13)	0.51776 (10)	0.0283 (4)
C19	0.89132 (17)	0.43040 (14)	0.62146 (11)	0.0323 (4)
C20	0.97073 (17)	0.33273 (15)	0.66605 (11)	0.0347 (4)
C21	0.94400 (18)	0.21266 (15)	0.61090 (12)	0.0357 (4)
C22	0.83119 (19)	0.19244 (15)	0.50894 (12)	0.0371 (4)
C23	0.75304 (17)	0.28937 (14)	0.46339 (11)	0.0328 (4)
C24	1.0340 (3)	0.10791 (18)	0.65903 (15)	0.0536 (6)
H1	0.20060	0.42600	−0.00920	0.0350*
H5	0.22240	0.60630	−0.16440	0.0360*
H6	0.04080	0.72610	−0.26910	0.0420*
H7	−0.11130	0.86890	−0.17690	0.0440*
H8	−0.07780	0.89580	0.02150	0.0430*
H9	0.11080	0.78260	0.12710	0.0360*
H11	0.56870	0.80090	0.03250	0.0360*
H12	0.66140	1.01550	0.07020	0.0430*
H13	0.60740	1.12650	0.23550	0.0500*
H14	0.47120	1.02200	0.36840	0.0530*
H15	0.38460	0.80710	0.33410	0.0430*
H16A	0.84650	0.68030	0.54040	0.0510*
H16B	0.69340	0.63410	0.60710	0.0510*
H16C	0.65380	0.69850	0.49190	0.0510*
H19	0.91060	0.51160	0.66190	0.0390*
H20	1.04510	0.34850	0.73600	0.0420*
H22	0.80820	0.11030	0.47050	0.0440*
H23	0.67750	0.27310	0.39400	0.0390*
H24A	1.14520	0.10640	0.63190	0.0800*
H24B	0.96450	0.02770	0.63440	0.0800*
H24C	1.05080	0.12150	0.74220	0.0800*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0294 (2)	0.0278 (2)	0.0296 (2)	−0.0005 (1)	−0.0006 (1)	0.0023 (1)
N1	0.0260 (5)	0.0270 (5)	0.0233 (5)	−0.0051 (4)	−0.0028 (4)	0.0006 (4)
N2	0.0311 (5)	0.0341 (6)	0.0279 (5)	−0.0028 (4)	−0.0036 (4)	0.0043 (4)
N3	0.0277 (5)	0.0358 (6)	0.0255 (5)	−0.0031 (4)	−0.0008 (4)	0.0040 (4)
C1	0.0282 (6)	0.0294 (6)	0.0273 (6)	−0.0009 (5)	−0.0031 (5)	−0.0007 (5)
C2	0.0221 (5)	0.0291 (6)	0.0213 (5)	−0.0028 (4)	0.0002 (4)	−0.0010 (4)
C3	0.0238 (5)	0.0312 (6)	0.0243 (6)	−0.0028 (5)	0.0020 (4)	0.0027 (5)
C4	0.0213 (5)	0.0258 (6)	0.0253 (6)	−0.0045 (4)	−0.0002 (4)	0.0004 (4)
C5	0.0262 (6)	0.0337 (7)	0.0265 (6)	−0.0027 (5)	−0.0002 (5)	−0.0026 (5)
C6	0.0334 (7)	0.0401 (8)	0.0277 (6)	−0.0067 (6)	−0.0064 (5)	0.0051 (5)
C7	0.0299 (6)	0.0306 (7)	0.0480 (8)	−0.0027 (5)	−0.0052 (6)	0.0112 (6)
C8	0.0319 (6)	0.0249 (6)	0.0491 (8)	0.0002 (5)	0.0068 (6)	0.0031 (6)
C9	0.0300 (6)	0.0275 (6)	0.0300 (6)	−0.0030 (5)	0.0043 (5)	−0.0008 (5)
C10	0.0234 (5)	0.0276 (6)	0.0260 (6)	−0.0037 (4)	−0.0022 (4)	−0.0004 (5)
C11	0.0292 (6)	0.0315 (7)	0.0258 (6)	−0.0018 (5)	0.0006 (5)	0.0007 (5)
C12	0.0333 (7)	0.0338 (7)	0.0369 (7)	−0.0064 (5)	−0.0017 (6)	0.0071 (6)
C13	0.0401 (8)	0.0297 (7)	0.0491 (9)	−0.0065 (6)	−0.0044 (6)	−0.0044 (6)
C14	0.0436 (8)	0.0439 (9)	0.0404 (8)	−0.0039 (7)	0.0045 (6)	−0.0158 (6)
C15	0.0331 (7)	0.0413 (8)	0.0306 (7)	−0.0064 (6)	0.0059 (5)	−0.0057 (6)
C16	0.0362 (7)	0.0374 (7)	0.0252 (6)	−0.0020 (6)	0.0002 (5)	0.0017 (5)
C17	0.0236 (5)	0.0349 (7)	0.0240 (6)	−0.0047 (5)	0.0021 (4)	0.0024 (5)
C18	0.0235 (6)	0.0380 (7)	0.0225 (6)	−0.0024 (5)	0.0041 (5)	0.0035 (5)
C19	0.0313 (6)	0.0379 (7)	0.0248 (6)	−0.0064 (5)	0.0009 (5)	0.0030 (5)
C20	0.0291 (6)	0.0480 (8)	0.0256 (6)	−0.0024 (6)	0.0001 (5)	0.0085 (6)
C21	0.0317 (7)	0.0482 (8)	0.0301 (7)	0.0097 (6)	0.0088 (5)	0.0077 (6)
C22	0.0386 (7)	0.0406 (8)	0.0321 (7)	0.0076 (6)	0.0068 (6)	−0.0027 (6)
C23	0.0317 (6)	0.0414 (8)	0.0235 (6)	0.0031 (5)	0.0009 (5)	−0.0024 (5)
C24	0.0609 (11)	0.0606 (11)	0.0427 (9)	0.0267 (9)	0.0043 (8)	0.0063 (8)

Geometric parameters (Å, º) top

S1—C1	1.7447 (13)	C19—C20	1.385 (2)
S1—C3	1.7559 (13)	C20—C21	1.383 (2)
N1—C2	1.4074 (16)	C21—C22	1.402 (2)
N1—C3	1.3823 (16)	C21—C24	1.505 (3)
N1—C10	1.4328 (17)	C22—C23	1.378 (2)
N2—N3	1.3983 (17)	C1—H1	0.9500
N2—C3	1.2894 (17)	C5—H5	0.9500
N3—C17	1.2946 (17)	C6—H6	0.9500
C1—C2	1.3381 (18)	C7—H7	0.9500
C2—C4	1.4762 (18)	C8—H8	0.9500
C4—C5	1.3938 (18)	C9—H9	0.9500
C4—C9	1.3986 (18)	C11—H11	0.9500
C5—C6	1.390 (2)	C12—H12	0.9500
C6—C7	1.383 (2)	C13—H13	0.9500
C7—C8	1.387 (2)	C14—H14	0.9500
C8—C9	1.384 (2)	C15—H15	0.9500
C10—C11	1.3834 (18)	C16—H16A	0.9800
C10—C15	1.3868 (19)	C16—H16B	0.9800
C11—C12	1.391 (2)	C16—H16C	0.9800
C12—C13	1.378 (2)	C19—H19	0.9500
C13—C14	1.391 (2)	C20—H20	0.9500
C14—C15	1.382 (2)	C22—H22	0.9500
C16—C17	1.4990 (19)	C23—H23	0.9500
C17—C18	1.4804 (19)	C24—H24A	0.9800
C18—C19	1.3996 (18)	C24—H24B	0.9800
C18—C23	1.399 (2)	C24—H24C	0.9800

C1—S1—C3	90.54 (6)	S1—C1—H1	124.00
C2—N1—C3	113.96 (10)	C2—C1—H1	124.00
C2—N1—C10	124.82 (11)	C4—C5—H5	120.00
C3—N1—C10	120.84 (10)	C6—C5—H5	120.00
N3—N2—C3	110.94 (11)	C5—C6—H6	120.00
N2—N3—C17	113.90 (11)	C7—C6—H6	120.00
S1—C1—C2	112.82 (10)	C6—C7—H7	120.00
N1—C2—C1	112.76 (11)	C8—C7—H7	120.00
N1—C2—C4	120.69 (11)	C7—C8—H8	120.00
C1—C2—C4	125.95 (11)	C9—C8—H8	120.00
S1—C3—N1	109.91 (9)	C4—C9—H9	120.00
S1—C3—N2	128.02 (10)	C8—C9—H9	120.00
N1—C3—N2	122.07 (12)	C10—C11—H11	120.00
C2—C4—C5	121.26 (11)	C12—C11—H11	120.00
C2—C4—C9	119.58 (11)	C11—C12—H12	120.00
C5—C4—C9	119.02 (12)	C13—C12—H12	120.00
C4—C5—C6	120.09 (12)	C12—C13—H13	120.00
C5—C6—C7	120.45 (13)	C14—C13—H13	120.00
C6—C7—C8	119.83 (13)	C13—C14—H14	120.00
C7—C8—C9	120.12 (13)	C15—C14—H14	120.00
C4—C9—C8	120.47 (12)	C10—C15—H15	120.00
N1—C10—C11	119.80 (11)	C14—C15—H15	120.00
N1—C10—C15	119.42 (12)	C17—C16—H16A	109.00
C11—C10—C15	120.78 (12)	C17—C16—H16B	109.00
C10—C11—C12	119.34 (12)	C17—C16—H16C	109.00
C11—C12—C13	120.31 (13)	H16A—C16—H16B	109.00
C12—C13—C14	119.87 (14)	H16A—C16—H16C	109.00
C13—C14—C15	120.31 (15)	H16B—C16—H16C	109.00
C10—C15—C14	119.35 (13)	C18—C19—H19	119.00
N3—C17—C16	124.23 (12)	C20—C19—H19	119.00
N3—C17—C18	116.36 (12)	C19—C20—H20	119.00
C16—C17—C18	119.37 (11)	C21—C20—H20	119.00
C17—C18—C19	121.26 (12)	C21—C22—H22	119.00
C17—C18—C23	121.15 (11)	C23—C22—H22	119.00
C19—C18—C23	117.54 (12)	C18—C23—H23	119.00
C18—C19—C20	121.03 (13)	C22—C23—H23	120.00
C19—C20—C21	121.36 (13)	C21—C24—H24A	109.00
C20—C21—C22	117.72 (14)	C21—C24—H24B	109.00
C20—C21—C24	120.83 (13)	C21—C24—H24C	109.00
C22—C21—C24	121.45 (15)	H24A—C24—H24B	110.00
C21—C22—C23	121.27 (14)	H24A—C24—H24C	109.00
C18—C23—C22	121.02 (12)	H24B—C24—H24C	109.00

C3—S1—C1—C2	−0.49 (11)	C2—C4—C9—C8	−174.46 (12)
C1—S1—C3—N1	−0.21 (9)	C5—C4—C9—C8	1.3 (2)
C1—S1—C3—N2	179.04 (13)	C4—C5—C6—C7	−1.0 (2)
C3—N1—C2—C1	−1.24 (15)	C5—C6—C7—C8	0.8 (2)
C3—N1—C2—C4	170.45 (11)	C6—C7—C8—C9	0.5 (2)
C10—N1—C2—C1	171.65 (11)	C7—C8—C9—C4	−1.6 (2)
C10—N1—C2—C4	−16.66 (18)	N1—C10—C11—C12	178.63 (12)
C2—N1—C3—S1	0.84 (13)	C15—C10—C11—C12	−1.2 (2)
C2—N1—C3—N2	−178.47 (12)	N1—C10—C15—C14	−177.75 (13)
C10—N1—C3—S1	−172.37 (9)	C11—C10—C15—C14	2.1 (2)
C10—N1—C3—N2	8.33 (18)	C10—C11—C12—C13	−0.6 (2)
C2—N1—C10—C11	−58.30 (17)	C11—C12—C13—C14	1.5 (2)
C2—N1—C10—C15	121.54 (14)	C12—C13—C14—C15	−0.6 (2)
C3—N1—C10—C11	114.13 (14)	C13—C14—C15—C10	−1.2 (2)
C3—N1—C10—C15	−66.03 (16)	N3—C17—C18—C19	168.14 (12)
C3—N2—N3—C17	−164.53 (12)	N3—C17—C18—C23	−9.15 (18)
N3—N2—C3—S1	2.76 (17)	C16—C17—C18—C19	−9.91 (18)
N3—N2—C3—N1	−178.07 (11)	C16—C17—C18—C23	172.80 (12)
N2—N3—C17—C16	2.60 (18)	C17—C18—C19—C20	−174.87 (12)
N2—N3—C17—C18	−175.34 (11)	C23—C18—C19—C20	2.51 (19)
S1—C1—C2—N1	1.06 (14)	C17—C18—C23—C22	175.55 (13)
S1—C1—C2—C4	−170.11 (10)	C19—C18—C23—C22	−1.8 (2)
N1—C2—C4—C5	136.04 (13)	C18—C19—C20—C21	−1.1 (2)
N1—C2—C4—C9	−48.28 (17)	C19—C20—C21—C22	−1.1 (2)
C1—C2—C4—C5	−53.44 (19)	C19—C20—C21—C24	178.69 (15)
C1—C2—C4—C9	122.24 (15)	C20—C21—C22—C23	1.8 (2)
C2—C4—C5—C6	175.69 (12)	C24—C21—C22—C23	−178.01 (15)
C9—C4—C5—C6	0.0 (2)	C21—C22—C23—C18	−0.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···S1ⁱ	0.98	3.03	4.0031 (14)	175
C16—H16C···N2	0.98	2.28	2.7053 (18)	105
C15—H15···Cg4ⁱ	0.95	2.71	3.6170 (16)	160
C16—H16A···Cg4ⁱⁱ	0.98	2.77	3.5984 (16)	143

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