5-(Adamantan-1-yl)-3-[(4-benzyl-piperazin-1-yl)meth-yl]-1,3,4-oxadiazole-2(3H)-thione.

The mol-ecule of the title compound, C(24)H(32)N(4)OS, is a functionalized 1,3,4-oxadiazole-2-thione with substituted piperazine and adamantanyl substituents attached at the 3- and 5-positions, respectively, of the oxadiazole spacer with an approximately C-shaped conformation. In the crystal, mol-ecules form dimers via C-H⋯S inter-action. The piperazine ring has a chair conformation; the substituents S, methyl-ene C and adamantane C of the essentially planar oxadiazole ring are approximately in the same plane, with distances of -0.046 (2), -0.085 (5) and 0.003 (4) Å, respectively. The dihedral angle between the planes of the phenyl and oxadiazole rings is 31.3 (3)°.

Related literature

For the biological activity of adamantyl-1,3,4-oxadiazole derivatives, see: Kadi et al. (2007 ▶, 2010 ▶); Al-Deeb et al. (2006 ▶), Vernier et al. (1969 ▶), El-Emam & Ibrahim (1991 ▶). For the synthesis of the title compound, see: El-Emam et al. (2004 ▶). For related adamantane structures, see: Almutairi et al. (2012 ▶); Al-Tamimi et al. (2010 ▶); Al-Abdullah et al. (2012 ▶). For related 1,3,4-oxadiazole structures, see: Fun et al. (2011 ▶); El-Emam et al. (2012 ▶).

Experimental

Crystal data

C24H32N4OS

M = 424.61

Monoclinic,

a = 11.6417 (9) Å

b = 17.198 (2) Å

c = 12.774 (1) Å

β = 115.06 (1)°

V = 2316.8 (4) Å3

Z = 4

Cu Kα radiation

μ = 1.41 mm−1

T = 293 K

0.11 × 0.09 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.857, T max = 0.975

9969 measured reflections

4368 independent reflections

2049 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.219

S = 1.01

4368 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶), PARST95 (Nardelli, 1995 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027249/ff2070sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027249/ff2070Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027249/ff2070Isup3.cml

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

C24H32N4OS	F(000) = 912
Mr = 424.61	Dx = 1.217 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 1030 reflections
a = 11.6417 (9) Å	θ = 3.8–70.6°
b = 17.198 (2) Å	µ = 1.41 mm−1
c = 12.774 (1) Å	T = 293 K
β = 115.06 (1)°	Prismatic, colourless
V = 2316.8 (4) Å3	0.11 × 0.09 × 0.02 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4368 independent reflections
Radiation source: fine-focus sealed tube	2049 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 10.2673 pixels mm-1	θmax = 70.7°, θmin = 4.2°
ω scans	h = −14→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −17→21
Tmin = 0.857, Tmax = 0.975	l = −15→15
9969 measured reflections

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0727P)2] where P = (Fo2 + 2Fc2)/3
4368 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. Absorption correction: CrysAlis PRO (Oxford Diffraction, 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
S1	0.87513 (13)	0.09736 (11)	0.58610 (13)	0.1011 (6)
O1	0.6438 (3)	0.15777 (18)	0.4778 (2)	0.0621 (8)
N3	0.8803 (3)	0.1628 (2)	0.2778 (3)	0.0581 (9)
N4	0.8057 (3)	0.0547 (2)	0.0914 (3)	0.0577 (9)
N2	0.7676 (3)	0.1910 (2)	0.3997 (3)	0.0588 (9)
N1	0.6514 (3)	0.2280 (2)	0.3359 (3)	0.0579 (9)
C1	0.5809 (4)	0.2066 (2)	0.3858 (3)	0.0502 (9)
C15	0.4469 (3)	0.2263 (2)	0.3571 (3)	0.0489 (9)
C6	0.7735 (4)	0.1783 (3)	0.1668 (4)	0.0606 (11)
H6A	0.7655	0.2339	0.1527	0.073*
H6B	0.6957	0.1599	0.1688	0.073*
C9	0.6932 (4)	0.0165 (3)	−0.1133 (4)	0.0623 (11)
C7	0.7926 (4)	0.1384 (3)	0.0711 (4)	0.0639 (11)
H7A	0.7208	0.1488	−0.0020	0.077*
H7B	0.8682	0.1586	0.0667	0.077*
C5	0.9163 (4)	0.0404 (3)	0.2003 (4)	0.0670 (12)
H5A	0.9917	0.0603	0.1952	0.080*
H5B	0.9271	−0.0152	0.2143	0.080*
C4	0.9009 (4)	0.0790 (3)	0.2991 (4)	0.0612 (11)
H4A	0.8293	0.0564	0.3080	0.073*
H4B	0.9763	0.0704	0.3701	0.073*
C16	0.4394 (4)	0.2710 (3)	0.4570 (4)	0.0722 (13)
H16A	0.4883	0.3186	0.4707	0.087*
H16B	0.4749	0.2398	0.5268	0.087*
C2	0.7658 (4)	0.1489 (3)	0.4861 (4)	0.0637 (11)
C8	0.8150 (4)	0.0136 (3)	−0.0047 (4)	0.0712 (13)
H8A	0.8372	−0.0403	0.0170	0.085*
H8B	0.8825	0.0366	−0.0200	0.085*
C3	0.8766 (4)	0.2065 (3)	0.3718 (4)	0.0651 (12)
H3A	0.8764	0.2613	0.3541	0.078*
H3B	0.9540	0.1961	0.4402	0.078*
C21	0.2521 (4)	0.2984 (4)	0.2190 (4)	0.0848 (16)
H21	0.2164	0.3313	0.1499	0.102*
C17	0.2980 (5)	0.2908 (3)	0.4275 (4)	0.0810 (15)
H17	0.2919	0.3189	0.4917	0.097*
C14	0.6870 (5)	0.0445 (3)	−0.2163 (4)	0.0781 (14)
H14	0.7604	0.0629	−0.2196	0.094*
C24	0.3926 (4)	0.2767 (4)	0.2486 (4)	0.0810 (15)
H24A	0.3967	0.2486	0.1844	0.097*
H24B	0.4427	0.3237	0.2610	0.097*
C10	0.5819 (4)	−0.0092 (3)	−0.1108 (4)	0.0698 (12)
H10	0.5831	−0.0273	−0.0417	0.084*
C19	0.2511 (5)	0.3400 (3)	0.3222 (5)	0.0881 (16)
H19A	0.3037	0.3861	0.3374	0.106*
H19B	0.1653	0.3566	0.3046	0.106*
C22	0.1798 (5)	0.2217 (4)	0.1996 (5)	0.098 (2)
H22A	0.0905	0.2324	0.1760	0.118*
H22B	0.1883	0.1931	0.1377	0.118*
C11	0.4697 (5)	−0.0085 (3)	−0.2086 (5)	0.0816 (15)
H11	0.3960	−0.0268	−0.2055	0.098*
C12	0.4655 (6)	0.0190 (3)	−0.3111 (5)	0.0928 (18)
H12	0.3895	0.0193	−0.3773	0.111*
C23	0.3697 (4)	0.1522 (3)	0.3371 (5)	0.0806 (15)
H23A	0.4032	0.1204	0.4064	0.097*
H23B	0.3751	0.1226	0.2747	0.097*
C20	0.2280 (5)	0.1735 (4)	0.3056 (5)	0.0895 (17)
H20	0.1774	0.1259	0.2921	0.107*
C18	0.2269 (5)	0.2162 (4)	0.4060 (5)	0.0908 (17)
H18A	0.2641	0.1837	0.4743	0.109*
H18B	0.1398	0.2269	0.3922	0.109*
C13	0.5746 (7)	0.0460 (3)	−0.3148 (5)	0.0962 (19)
H13	0.5727	0.0652	−0.3835	0.115*

	U11	U22	U33	U12	U13	U23
S1	0.0724 (8)	0.1413 (14)	0.0814 (9)	0.0392 (9)	0.0245 (7)	0.0333 (9)
O1	0.0553 (16)	0.078 (2)	0.0531 (16)	0.0100 (15)	0.0228 (13)	0.0091 (15)
N3	0.0456 (17)	0.062 (2)	0.065 (2)	0.0015 (16)	0.0219 (16)	−0.0016 (18)
N4	0.0491 (17)	0.060 (2)	0.058 (2)	0.0056 (16)	0.0174 (16)	0.0011 (17)
N2	0.0415 (17)	0.071 (2)	0.063 (2)	0.0038 (16)	0.0215 (15)	0.0008 (18)
N1	0.0446 (17)	0.066 (2)	0.063 (2)	0.0033 (16)	0.0225 (16)	0.0017 (18)
C1	0.046 (2)	0.053 (2)	0.047 (2)	−0.0005 (18)	0.0147 (17)	−0.0036 (18)
C15	0.0444 (19)	0.056 (2)	0.044 (2)	−0.0053 (17)	0.0167 (16)	−0.0058 (18)
C6	0.052 (2)	0.062 (3)	0.063 (3)	0.005 (2)	0.020 (2)	0.005 (2)
C9	0.061 (3)	0.063 (3)	0.063 (3)	−0.001 (2)	0.026 (2)	−0.006 (2)
C7	0.058 (2)	0.064 (3)	0.069 (3)	0.002 (2)	0.027 (2)	0.009 (2)
C5	0.048 (2)	0.061 (3)	0.077 (3)	0.003 (2)	0.012 (2)	−0.003 (2)
C4	0.045 (2)	0.067 (3)	0.060 (3)	0.0044 (19)	0.0115 (18)	0.004 (2)
C16	0.050 (2)	0.096 (4)	0.066 (3)	0.001 (2)	0.021 (2)	−0.016 (3)
C2	0.047 (2)	0.076 (3)	0.062 (3)	0.009 (2)	0.018 (2)	0.001 (2)
C8	0.055 (2)	0.084 (3)	0.072 (3)	0.001 (2)	0.025 (2)	−0.006 (3)
C3	0.041 (2)	0.081 (3)	0.072 (3)	−0.005 (2)	0.023 (2)	−0.009 (2)
C21	0.058 (3)	0.129 (5)	0.061 (3)	0.007 (3)	0.020 (2)	0.020 (3)
C17	0.076 (3)	0.105 (4)	0.070 (3)	0.003 (3)	0.037 (3)	−0.015 (3)
C14	0.099 (4)	0.068 (3)	0.078 (3)	−0.008 (3)	0.047 (3)	0.001 (3)
C24	0.064 (3)	0.110 (4)	0.070 (3)	0.018 (3)	0.029 (2)	0.020 (3)
C10	0.064 (3)	0.074 (3)	0.070 (3)	−0.004 (2)	0.028 (2)	0.001 (2)
C19	0.083 (3)	0.085 (4)	0.103 (4)	0.019 (3)	0.046 (3)	0.002 (3)
C22	0.062 (3)	0.140 (5)	0.070 (3)	0.017 (3)	0.005 (3)	−0.025 (4)
C11	0.059 (3)	0.074 (3)	0.096 (4)	−0.003 (2)	0.018 (3)	−0.008 (3)
C12	0.088 (4)	0.073 (3)	0.083 (4)	0.010 (3)	0.002 (3)	−0.015 (3)
C23	0.061 (3)	0.071 (3)	0.101 (4)	−0.010 (2)	0.025 (3)	−0.005 (3)
C20	0.072 (3)	0.091 (4)	0.107 (5)	−0.023 (3)	0.038 (3)	−0.016 (4)
C18	0.064 (3)	0.123 (5)	0.089 (4)	−0.004 (3)	0.035 (3)	0.012 (4)
C13	0.134 (5)	0.077 (4)	0.069 (4)	0.009 (4)	0.034 (4)	0.004 (3)

S1—C2	1.631 (4)	C8—H8B	0.9700
O1—C1	1.376 (5)	C3—H3A	0.9700
O1—C2	1.387 (5)	C3—H3B	0.9700
N3—C3	1.432 (6)	C21—C19	1.504 (8)
N3—C6	1.461 (5)	C21—C22	1.528 (9)
N3—C4	1.468 (6)	C21—C24	1.560 (7)
N4—C7	1.459 (6)	C21—H21	0.9800
N4—C8	1.460 (6)	C17—C19	1.484 (8)
N4—C5	1.462 (5)	C17—C18	1.487 (8)
N2—C2	1.327 (6)	C17—H17	0.9800
N2—N1	1.403 (5)	C14—C13	1.379 (8)
N2—C3	1.480 (5)	C14—H14	0.9300
N1—C1	1.287 (5)	C24—H24A	0.9700
C1—C15	1.483 (5)	C24—H24B	0.9700
C15—C23	1.518 (6)	C10—C11	1.374 (6)
C15—C16	1.524 (6)	C10—H10	0.9300
C15—C24	1.526 (6)	C19—H19A	0.9700
C6—C7	1.498 (6)	C19—H19B	0.9700
C6—H6A	0.9700	C22—C20	1.481 (8)
C6—H6B	0.9700	C22—H22A	0.9700
C9—C14	1.372 (7)	C22—H22B	0.9700
C9—C10	1.382 (6)	C11—C12	1.373 (8)
C9—C8	1.508 (6)	C11—H11	0.9300
C7—H7A	0.9700	C12—C13	1.371 (8)
C7—H7B	0.9700	C12—H12	0.9300
C5—C4	1.503 (6)	C23—C20	1.566 (7)
C5—H5A	0.9700	C23—H23A	0.9700
C5—H5B	0.9700	C23—H23B	0.9700
C4—H4A	0.9700	C20—C18	1.483 (8)
C4—H4B	0.9700	C20—H20	0.9800
C16—C17	1.562 (7)	C18—H18A	0.9700
C16—H16A	0.9700	C18—H18B	0.9700
C16—H16B	0.9700	C13—H13	0.9300
C8—H8A	0.9700
C1—O1—C2	106.8 (3)	N2—C3—H3B	108.2
C3—N3—C6	113.7 (3)	H3A—C3—H3B	107.4
C3—N3—C4	114.8 (4)	C19—C21—C22	110.2 (5)
C6—N3—C4	111.3 (3)	C19—C21—C24	107.3 (4)
C7—N4—C8	111.5 (4)	C22—C21—C24	106.3 (5)
C7—N4—C5	108.6 (3)	C19—C21—H21	111.0
C8—N4—C5	111.7 (3)	C22—C21—H21	111.0
C2—N2—N1	112.3 (3)	C24—C21—H21	111.0
C2—N2—C3	128.0 (4)	C19—C17—C18	111.2 (4)
N1—N2—C3	119.5 (4)	C19—C17—C16	106.8 (4)
C1—N1—N2	104.0 (3)	C18—C17—C16	107.7 (5)
N1—C1—O1	112.2 (3)	C19—C17—H17	110.4
N1—C1—C15	129.5 (4)	C18—C17—H17	110.4
O1—C1—C15	118.3 (3)	C16—C17—H17	110.4
C1—C15—C23	109.6 (4)	C9—C14—C13	121.7 (5)
C1—C15—C16	109.7 (3)	C9—C14—H14	119.1
C23—C15—C16	108.9 (4)	C13—C14—H14	119.1
C1—C15—C24	110.0 (3)	C15—C24—C21	110.2 (4)
C23—C15—C24	109.6 (4)	C15—C24—H24A	109.6
C16—C15—C24	109.0 (4)	C21—C24—H24A	109.6
N3—C6—C7	110.4 (4)	C15—C24—H24B	109.6
N3—C6—H6A	109.6	C21—C24—H24B	109.6
C7—C6—H6A	109.6	H24A—C24—H24B	108.1
N3—C6—H6B	109.6	C11—C10—C9	121.0 (5)
C7—C6—H6B	109.6	C11—C10—H10	119.5
H6A—C6—H6B	108.1	C9—C10—H10	119.5
C14—C9—C10	117.7 (4)	C17—C19—C21	112.8 (5)
C14—C9—C8	122.7 (5)	C17—C19—H19A	109.0
C10—C9—C8	119.5 (4)	C21—C19—H19A	109.0
N4—C7—C6	110.3 (4)	C17—C19—H19B	109.0
N4—C7—H7A	109.6	C21—C19—H19B	109.0
C6—C7—H7A	109.6	H19A—C19—H19B	107.8
N4—C7—H7B	109.6	C20—C22—C21	111.5 (4)
C6—C7—H7B	109.6	C20—C22—H22A	109.3
H7A—C7—H7B	108.1	C21—C22—H22A	109.3
N4—C5—C4	110.7 (4)	C20—C22—H22B	109.3
N4—C5—H5A	109.5	C21—C22—H22B	109.3
C4—C5—H5A	109.5	H22A—C22—H22B	108.0
N4—C5—H5B	109.5	C12—C11—C10	120.4 (5)
C4—C5—H5B	109.5	C12—C11—H11	119.8
H5A—C5—H5B	108.1	C10—C11—H11	119.8
N3—C4—C5	110.3 (4)	C13—C12—C11	119.3 (5)
N3—C4—H4A	109.6	C13—C12—H12	120.3
C5—C4—H4A	109.6	C11—C12—H12	120.3
N3—C4—H4B	109.6	C15—C23—C20	109.3 (4)
C5—C4—H4B	109.6	C15—C23—H23A	109.8
H4A—C4—H4B	108.1	C20—C23—H23A	109.8
C15—C16—C17	109.7 (3)	C15—C23—H23B	109.8
C15—C16—H16A	109.7	C20—C23—H23B	109.8
C17—C16—H16A	109.7	H23A—C23—H23B	108.3
C15—C16—H16B	109.7	C22—C20—C18	112.0 (5)
C17—C16—H16B	109.7	C22—C20—C23	108.4 (5)
H16A—C16—H16B	108.2	C18—C20—C23	106.7 (5)
N2—C2—O1	104.7 (3)	C22—C20—H20	109.9
N2—C2—S1	131.7 (3)	C18—C20—H20	109.9
O1—C2—S1	123.6 (4)	C23—C20—H20	109.9
N4—C8—C9	112.4 (4)	C20—C18—C17	112.2 (5)
N4—C8—H8A	109.1	C20—C18—H18A	109.2
C9—C8—H8A	109.1	C17—C18—H18A	109.2
N4—C8—H8B	109.1	C20—C18—H18B	109.2
C9—C8—H8B	109.1	C17—C18—H18B	109.2
H8A—C8—H8B	107.9	H18A—C18—H18B	107.9
N3—C3—N2	116.2 (3)	C12—C13—C14	119.8 (6)
N3—C3—H3A	108.2	C12—C13—H13	120.1
N2—C3—H3A	108.2	C14—C13—H13	120.1
N3—C3—H3B	108.2
C2—N2—N1—C1	−0.5 (5)	C4—N3—C3—N2	−67.1 (5)
C3—N2—N1—C1	−175.9 (4)	C2—N2—C3—N3	102.8 (5)
N2—N1—C1—O1	−0.1 (4)	N1—N2—C3—N3	−82.5 (5)
N2—N1—C1—C15	−179.5 (4)	C15—C16—C17—C19	−60.8 (6)
C2—O1—C1—N1	0.7 (4)	C15—C16—C17—C18	58.7 (6)
C2—O1—C1—C15	−179.9 (3)	C10—C9—C14—C13	−1.0 (8)
N1—C1—C15—C23	123.4 (5)	C8—C9—C14—C13	179.4 (5)
O1—C1—C15—C23	−55.9 (5)	C1—C15—C24—C21	−179.3 (4)
N1—C1—C15—C16	−117.1 (5)	C23—C15—C24—C21	60.1 (6)
O1—C1—C15—C16	63.5 (5)	C16—C15—C24—C21	−59.0 (5)
N1—C1—C15—C24	2.8 (6)	C19—C21—C24—C15	58.0 (6)
O1—C1—C15—C24	−176.5 (4)	C22—C21—C24—C15	−59.9 (6)
C3—N3—C6—C7	172.9 (4)	C14—C9—C10—C11	1.5 (7)
C4—N3—C6—C7	−55.5 (5)	C8—C9—C10—C11	−178.9 (5)
C8—N4—C7—C6	175.8 (3)	C18—C17—C19—C21	−54.3 (6)
C5—N4—C7—C6	−60.7 (5)	C16—C17—C19—C21	62.9 (6)
N3—C6—C7—N4	58.8 (5)	C22—C21—C19—C17	53.6 (6)
C7—N4—C5—C4	60.2 (5)	C24—C21—C19—C17	−61.7 (6)
C8—N4—C5—C4	−176.4 (4)	C19—C21—C22—C20	−53.4 (6)
C3—N3—C4—C5	−174.3 (3)	C24—C21—C22—C20	62.6 (6)
C6—N3—C4—C5	54.7 (5)	C9—C10—C11—C12	−1.0 (8)
N4—C5—C4—N3	−57.3 (5)	C10—C11—C12—C13	−0.2 (9)
C1—C15—C16—C17	−179.2 (4)	C1—C15—C23—C20	−179.4 (4)
C23—C15—C16—C17	−59.3 (5)	C16—C15—C23—C20	60.7 (5)
C24—C15—C16—C17	60.3 (5)	C24—C15—C23—C20	−58.5 (6)
N1—N2—C2—O1	0.9 (5)	C21—C22—C20—C18	54.6 (6)
C3—N2—C2—O1	175.8 (4)	C21—C22—C20—C23	−62.8 (6)
N1—N2—C2—S1	−178.2 (4)	C15—C23—C20—C22	59.6 (6)
C3—N2—C2—S1	−3.3 (8)	C15—C23—C20—C18	−61.2 (6)
C1—O1—C2—N2	−0.9 (4)	C22—C20—C18—C17	−55.2 (6)
C1—O1—C2—S1	178.3 (3)	C23—C20—C18—C17	63.3 (6)
C7—N4—C8—C9	−67.9 (5)	C19—C17—C18—C20	54.3 (6)
C5—N4—C8—C9	170.4 (4)	C16—C17—C18—C20	−62.4 (6)
C14—C9—C8—N4	124.2 (5)	C11—C12—C13—C14	0.7 (9)
C10—C9—C8—N4	−55.3 (6)	C9—C14—C13—C12	−0.1 (9)
C6—N3—C3—N2	62.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···S1i	0.97	2.97	3.652 (5)	128 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯S1i	0.97	2.97	3.652 (5)	128 (1)

Symmetry code: (i) .