3-(Adamantan-1-yl)-4-ethyl-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione.

The title compound, C(25)H(35)N(5)S, has an approximately C-shaped conformation. The dihedral angle between the triazole and phenyl planes is 79.5 (2)°. The crystal structure consists of infinite chains parallel to the b axis, constructed by C-H⋯S hydrogen bonds between translation-related mol-ecules. Adjacent chains are linked via weak C-H⋯C inter-actions between the adamantyl and phenyl groups.

Related literature

For the biological activity of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Vernier et al. (1969 ▶); Al-Deeb et al. (2006 ▶); Al-Omar et al. (2010 ▶); El-Emam & Ibrahim (1991 ▶); El-Emam et al. (2004 ▶); Kadi et al. (2007 ▶, 2010 ▶). For related adamantyl-1,2,4-triazole structures, see: Al-Tamimi et al. (2010 ▶); Al-Abdullah et al. (2012 ▶); El-Emam et al. (2012 ▶); Lahsasni et al. (2012 ▶).

Experimental

Crystal data

C25H35N5S

M = 437.65

Orthorhombic,

a = 27.382 (4) Å

b = 6.5083 (7) Å

c = 13.369 (2) Å

V = 2382.4 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.36 mm−1

T = 293 K

0.16 × 0.06 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.919, T max = 1.000

5844 measured reflections

3016 independent reflections

1828 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.128

S = 1.00

3016 reflections

282 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 632 Friedel pairs

Flack parameter: 0.00 (4)

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 ▶); data reduction: CrysAlis RED; 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 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202990X/fy2061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202990X/fy2061Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202990X/fy2061Isup3.cml

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

C25H35N5S	F(000) = 944
Mr = 437.65	Dx = 1.220 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2n	Cell parameters from 728 reflections
a = 27.382 (4) Å	θ = 3.7–70.5°
b = 6.5083 (7) Å	µ = 1.36 mm−1
c = 13.369 (2) Å	T = 293 K
V = 2382.4 (5) Å3	Prism, colourless
Z = 4	0.16 × 0.06 × 0.02 mm

Oxford Diffraction Xcalibur Gemini R diffractometer	3016 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
Detector resolution: 10.2673 pixels mm-1	θmax = 70.7°, θmin = 4.6°
ω scans	h = −27→32
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→7
Tmin = 0.919, Tmax = 1.000	l = −9→16
5844 measured reflections

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0292P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3016 reflections	Δρmax = 0.17 e Å−3
282 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: Flack (1983), 632 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (4)

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	0.47530 (6)	0.0990 (2)	0.88657 (13)	0.0661 (4)
N1	0.40642 (17)	0.4993 (7)	1.0508 (3)	0.0559 (11)
N2	0.42569 (16)	0.4251 (7)	0.9622 (3)	0.0533 (11)
N3	0.44288 (16)	0.2016 (7)	1.0746 (3)	0.0495 (10)
N4	0.37594 (16)	0.5467 (7)	0.8271 (4)	0.0536 (11)
N5	0.30519 (17)	0.5670 (7)	0.6693 (3)	0.0540 (11)
C1	0.41610 (19)	0.3589 (8)	1.1182 (4)	0.0486 (12)
C2	0.39947 (19)	0.3789 (8)	1.2243 (4)	0.0498 (12)
C3	0.3646 (2)	0.1977 (9)	1.2515 (5)	0.0634 (15)
H3A	0.3370	0.1958	1.2060	0.076*
H3B	0.3819	0.0681	1.2452	0.076*
C4	0.3465 (3)	0.2256 (11)	1.3600 (5)	0.0765 (19)
H4	0.3253	0.1100	1.3776	0.092*
C5	0.3177 (2)	0.4225 (11)	1.3669 (6)	0.0805 (19)
H5A	0.3045	0.4378	1.4339	0.097*
H5B	0.2906	0.4186	1.3202	0.097*
C6	0.3508 (3)	0.6039 (11)	1.3427 (5)	0.0764 (19)
H6	0.3323	0.7322	1.3478	0.092*
C7	0.3692 (2)	0.5759 (9)	1.2349 (5)	0.0671 (16)
H7A	0.3416	0.5701	1.1897	0.081*
H7B	0.3891	0.6932	1.2162	0.081*
C8	0.4414 (2)	0.3859 (11)	1.2987 (4)	0.0672 (16)
H8A	0.4627	0.4999	1.2824	0.081*
H8B	0.4602	0.2601	1.2937	0.081*
C9	0.4223 (3)	0.4110 (12)	1.4070 (5)	0.082 (2)
H9	0.4499	0.4153	1.4537	0.099*
C10	0.3897 (3)	0.2300 (12)	1.4314 (5)	0.092 (2)
H10A	0.3781	0.2413	1.4997	0.110*
H10B	0.4081	0.1033	1.4254	0.110*
C11	0.3934 (3)	0.6097 (11)	1.4138 (5)	0.089 (2)
H11A	0.3815	0.6282	1.4816	0.107*
H11B	0.4143	0.7250	1.3975	0.107*
C12	0.4659 (2)	0.0198 (9)	1.1198 (5)	0.0650 (17)
H12A	0.4599	−0.0992	1.0779	0.078*
H12B	0.4514	−0.0060	1.1848	0.078*
C13	0.5207 (2)	0.0501 (14)	1.1319 (6)	0.096 (3)
H13A	0.5352	−0.0745	1.1563	0.143*
H13B	0.5267	0.1593	1.1786	0.143*
H13C	0.5348	0.0847	1.0683	0.143*
C14	0.4485 (2)	0.2439 (8)	0.9739 (4)	0.0487 (12)
C15	0.42363 (18)	0.5519 (8)	0.8724 (4)	0.0561 (14)
H15A	0.4318	0.6926	0.8895	0.067*
H15B	0.4477	0.5031	0.8246	0.067*
C16	0.3704 (2)	0.3810 (9)	0.7556 (5)	0.0640 (15)
H16A	0.3784	0.2514	0.7875	0.077*
H16B	0.3929	0.4013	0.7004	0.077*
C17	0.3181 (2)	0.3728 (9)	0.7154 (5)	0.0670 (17)
H17A	0.3153	0.2632	0.6666	0.080*
H17B	0.2957	0.3436	0.7699	0.080*
C18	0.3126 (2)	0.7352 (11)	0.7401 (5)	0.077 (2)
H18A	0.2907	0.7184	0.7964	0.092*
H18B	0.3049	0.8646	0.7078	0.092*
C19	0.3642 (2)	0.7407 (10)	0.7770 (5)	0.0707 (17)
H19A	0.3863	0.7619	0.7211	0.085*
H19B	0.3683	0.8540	0.8234	0.085*
C20	0.2619 (2)	0.5739 (9)	0.6120 (4)	0.0587 (14)
C21	0.2322 (2)	0.4026 (11)	0.5996 (4)	0.0650 (16)
H21	0.2393	0.2810	0.6331	0.078*
C22	0.1913 (2)	0.4140 (12)	0.5361 (5)	0.0732 (18)
H22	0.1719	0.2983	0.5260	0.088*
C23	0.1798 (2)	0.5956 (12)	0.4890 (5)	0.0775 (19)
H23	0.1523	0.6035	0.4482	0.093*
C24	0.2089 (3)	0.7651 (12)	0.5023 (5)	0.0766 (19)
H24	0.2006	0.8880	0.4711	0.092*
C25	0.2496 (2)	0.7563 (10)	0.5605 (4)	0.0688 (16)
H25	0.2695	0.8714	0.5665	0.083*

	U11	U22	U33	U12	U13	U23
S1	0.0731 (8)	0.0694 (8)	0.0558 (8)	0.0032 (8)	0.0078 (9)	−0.0078 (9)
N1	0.061 (3)	0.059 (3)	0.048 (3)	0.003 (2)	0.000 (2)	−0.004 (2)
N2	0.059 (2)	0.056 (3)	0.045 (2)	0.000 (2)	0.003 (2)	0.003 (2)
N3	0.053 (2)	0.050 (2)	0.046 (2)	0.002 (2)	−0.003 (2)	−0.005 (2)
N4	0.056 (2)	0.053 (3)	0.052 (2)	0.001 (2)	−0.006 (2)	0.001 (2)
N5	0.058 (3)	0.048 (2)	0.056 (3)	−0.001 (2)	−0.010 (2)	0.004 (2)
C1	0.048 (3)	0.046 (3)	0.051 (3)	−0.001 (2)	−0.005 (3)	0.005 (2)
C2	0.051 (3)	0.047 (3)	0.052 (3)	−0.001 (3)	−0.002 (3)	−0.003 (2)
C3	0.073 (4)	0.059 (3)	0.058 (4)	−0.006 (3)	0.010 (3)	−0.007 (3)
C4	0.102 (5)	0.066 (4)	0.062 (4)	−0.014 (4)	0.024 (4)	−0.007 (3)
C5	0.078 (4)	0.087 (5)	0.077 (5)	−0.008 (4)	0.023 (4)	−0.015 (4)
C6	0.089 (4)	0.070 (4)	0.070 (4)	0.012 (4)	0.016 (4)	−0.011 (3)
C7	0.085 (4)	0.054 (3)	0.063 (4)	0.011 (3)	0.008 (3)	−0.004 (3)
C8	0.066 (3)	0.082 (4)	0.055 (4)	−0.000 (3)	−0.005 (3)	−0.011 (3)
C9	0.090 (4)	0.106 (5)	0.051 (4)	0.007 (5)	−0.012 (4)	−0.012 (4)
C10	0.133 (7)	0.087 (5)	0.056 (4)	0.025 (5)	0.017 (5)	0.003 (4)
C11	0.117 (6)	0.078 (4)	0.072 (5)	−0.007 (5)	0.012 (4)	−0.030 (3)
C12	0.082 (4)	0.057 (3)	0.056 (3)	0.018 (3)	0.007 (4)	0.010 (3)
C13	0.072 (4)	0.143 (7)	0.072 (4)	0.038 (5)	0.004 (4)	0.019 (5)
C14	0.048 (3)	0.055 (3)	0.043 (3)	−0.006 (3)	0.001 (3)	0.000 (2)
C15	0.058 (3)	0.063 (3)	0.048 (3)	−0.002 (3)	−0.000 (3)	0.010 (3)
C16	0.071 (3)	0.049 (3)	0.072 (4)	0.005 (3)	−0.010 (3)	−0.004 (3)
C17	0.077 (4)	0.051 (3)	0.073 (4)	−0.002 (3)	−0.015 (3)	0.006 (3)
C18	0.083 (4)	0.063 (4)	0.084 (5)	0.015 (4)	−0.019 (4)	−0.009 (4)
C19	0.084 (4)	0.058 (4)	0.070 (4)	0.000 (4)	−0.012 (4)	0.005 (3)
C20	0.059 (3)	0.062 (3)	0.055 (3)	0.006 (3)	0.001 (3)	−0.001 (3)
C21	0.061 (3)	0.071 (4)	0.062 (4)	−0.006 (3)	−0.002 (3)	0.003 (3)
C22	0.061 (3)	0.089 (5)	0.070 (4)	0.001 (4)	−0.006 (3)	−0.005 (4)
C23	0.069 (4)	0.099 (6)	0.064 (4)	0.020 (4)	−0.011 (3)	−0.011 (4)
C24	0.086 (5)	0.082 (5)	0.062 (4)	0.023 (4)	−0.018 (4)	−0.001 (4)
C25	0.077 (4)	0.064 (4)	0.065 (4)	0.007 (3)	−0.012 (4)	0.006 (3)

S1—C14	1.670 (6)	C9—C11	1.520 (10)
N1—C1	1.311 (7)	C9—H9	0.9800
N1—N2	1.384 (6)	C10—H10A	0.9700
N2—C14	1.344 (7)	C10—H10B	0.9700
N2—C15	1.459 (7)	C11—H11A	0.9700
N3—C14	1.383 (7)	C11—H11B	0.9700
N3—C1	1.388 (7)	C12—C13	1.522 (9)
N3—C12	1.471 (7)	C12—H12A	0.9700
N4—C15	1.440 (7)	C12—H12B	0.9700
N4—C16	1.449 (7)	C13—H13A	0.9600
N4—C19	1.465 (7)	C13—H13B	0.9600
N5—C20	1.412 (7)	C13—H13C	0.9600
N5—C17	1.450 (8)	C15—H15A	0.9700
N5—C18	1.461 (8)	C15—H15B	0.9700
C1—C2	1.495 (8)	C16—C17	1.530 (8)
C2—C8	1.518 (8)	C16—H16A	0.9700
C2—C7	1.533 (8)	C16—H16B	0.9700
C2—C3	1.560 (8)	C17—H17A	0.9700
C3—C4	1.544 (8)	C17—H17B	0.9700
C3—H3A	0.9700	C18—C19	1.496 (9)
C3—H3B	0.9700	C18—H18A	0.9700
C4—C5	1.509 (9)	C18—H18B	0.9700
C4—C10	1.520 (10)	C19—H19A	0.9700
C4—H4	0.9800	C19—H19B	0.9700
C5—C6	1.525 (9)	C20—C21	1.390 (8)
C5—H5A	0.9700	C20—C25	1.413 (8)
C5—H5B	0.9700	C21—C22	1.408 (9)
C6—C11	1.504 (10)	C21—H21	0.9300
C6—C7	1.538 (9)	C22—C23	1.376 (10)
C6—H6	0.9800	C22—H22	0.9300
C7—H7A	0.9700	C23—C24	1.373 (10)
C7—H7B	0.9700	C23—H23	0.9300
C8—C9	1.548 (9)	C24—C25	1.361 (9)
C8—H8A	0.9700	C24—H24	0.9300
C8—H8B	0.9700	C25—H25	0.9300
C9—C10	1.514 (11)
C1—N1—N2	105.6 (4)	C6—C11—C9	110.2 (6)
C14—N2—N1	112.6 (4)	C6—C11—H11A	109.6
C14—N2—C15	127.6 (5)	C9—C11—H11A	109.6
N1—N2—C15	119.5 (4)	C6—C11—H11B	109.6
C14—N3—C1	108.7 (4)	C9—C11—H11B	109.6
C14—N3—C12	120.9 (5)	H11A—C11—H11B	108.1
C1—N3—C12	130.3 (4)	N3—C12—C13	111.2 (5)
C15—N4—C16	112.9 (5)	N3—C12—H12A	109.4
C15—N4—C19	111.8 (5)	C13—C12—H12A	109.4
C16—N4—C19	108.5 (5)	N3—C12—H12B	109.4
C20—N5—C17	117.6 (5)	C13—C12—H12B	109.4
C20—N5—C18	116.4 (5)	H12A—C12—H12B	108.0
C17—N5—C18	110.1 (5)	C12—C13—H13A	109.5
N1—C1—N3	109.4 (5)	C12—C13—H13B	109.5
N1—C1—C2	122.0 (5)	H13A—C13—H13B	109.5
N3—C1—C2	128.6 (5)	C12—C13—H13C	109.5
C1—C2—C8	113.2 (4)	H13A—C13—H13C	109.5
C1—C2—C7	108.9 (5)	H13B—C13—H13C	109.5
C8—C2—C7	108.8 (5)	N2—C14—N3	103.6 (5)
C1—C2—C3	110.0 (4)	N2—C14—S1	128.2 (4)
C8—C2—C3	109.4 (5)	N3—C14—S1	128.1 (4)
C7—C2—C3	106.3 (5)	N4—C15—N2	111.6 (4)
C4—C3—C2	109.0 (5)	N4—C15—H15A	109.3
C4—C3—H3A	109.9	N2—C15—H15A	109.3
C2—C3—H3A	109.9	N4—C15—H15B	109.3
C4—C3—H3B	109.9	N2—C15—H15B	109.3
C2—C3—H3B	109.9	H15A—C15—H15B	108.0
H3A—C3—H3B	108.3	N4—C16—C17	110.8 (5)
C5—C4—C10	110.7 (6)	N4—C16—H16A	109.5
C5—C4—C3	109.0 (6)	C17—C16—H16A	109.5
C10—C4—C3	110.0 (6)	N4—C16—H16B	109.5
C5—C4—H4	109.0	C17—C16—H16B	109.5
C10—C4—H4	109.0	H16A—C16—H16B	108.1
C3—C4—H4	109.0	N5—C17—C16	110.3 (5)
C4—C5—C6	109.4 (5)	N5—C17—H17A	109.6
C4—C5—H5A	109.8	C16—C17—H17A	109.6
C6—C5—H5A	109.8	N5—C17—H17B	109.6
C4—C5—H5B	109.8	C16—C17—H17B	109.6
C6—C5—H5B	109.8	H17A—C17—H17B	108.1
H5A—C5—H5B	108.2	N5—C18—C19	111.3 (5)
C11—C6—C5	110.3 (6)	N5—C18—H18A	109.4
C11—C6—C7	110.0 (5)	C19—C18—H18A	109.4
C5—C6—C7	107.6 (6)	N5—C18—H18B	109.4
C11—C6—H6	109.6	C19—C18—H18B	109.4
C5—C6—H6	109.6	H18A—C18—H18B	108.0
C7—C6—H6	109.6	N4—C19—C18	109.7 (6)
C2—C7—C6	111.2 (5)	N4—C19—H19A	109.7
C2—C7—H7A	109.4	C18—C19—H19A	109.7
C6—C7—H7A	109.4	N4—C19—H19B	109.7
C2—C7—H7B	109.4	C18—C19—H19B	109.7
C6—C7—H7B	109.4	H19A—C19—H19B	108.2
H7A—C7—H7B	108.0	C21—C20—N5	122.0 (5)
C2—C8—C9	111.2 (5)	C21—C20—C25	118.4 (5)
C2—C8—H8A	109.4	N5—C20—C25	119.4 (6)
C9—C8—H8A	109.4	C20—C21—C22	119.7 (6)
C2—C8—H8B	109.4	C20—C21—H21	120.1
C9—C8—H8B	109.4	C22—C21—H21	120.1
H8A—C8—H8B	108.0	C23—C22—C21	120.2 (7)
C10—C9—C11	110.0 (7)	C23—C22—H22	119.9
C10—C9—C8	108.5 (6)	C21—C22—H22	119.9
C11—C9—C8	108.8 (6)	C24—C23—C22	119.9 (6)
C10—C9—H9	109.9	C24—C23—H23	120.0
C11—C9—H9	109.9	C22—C23—H23	120.0
C8—C9—H9	109.9	C25—C24—C23	121.1 (7)
C9—C10—C4	109.8 (6)	C25—C24—H24	119.5
C9—C10—H10A	109.7	C23—C24—H24	119.5
C4—C10—H10A	109.7	C24—C25—C20	120.6 (7)
C9—C10—H10B	109.7	C24—C25—H25	119.7
C4—C10—H10B	109.7	C20—C25—H25	119.7
H10A—C10—H10B	108.2
C1—N1—N2—C14	−1.9 (6)	C10—C9—C11—C6	−58.7 (7)
C1—N1—N2—C15	−176.4 (5)	C8—C9—C11—C6	60.0 (8)
N2—N1—C1—N3	2.4 (6)	C14—N3—C12—C13	74.2 (7)
N2—N1—C1—C2	−177.8 (5)	C1—N3—C12—C13	−101.9 (7)
C14—N3—C1—N1	−2.2 (6)	N1—N2—C14—N3	0.5 (6)
C12—N3—C1—N1	174.2 (5)	C15—N2—C14—N3	174.4 (5)
C14—N3—C1—C2	178.0 (5)	N1—N2—C14—S1	178.2 (4)
C12—N3—C1—C2	−5.6 (9)	C15—N2—C14—S1	−7.9 (9)
N1—C1—C2—C8	−118.6 (6)	C1—N3—C14—N2	1.0 (6)
N3—C1—C2—C8	61.1 (8)	C12—N3—C14—N2	−175.9 (5)
N1—C1—C2—C7	2.5 (7)	C1—N3—C14—S1	−176.7 (4)
N3—C1—C2—C7	−177.7 (5)	C12—N3—C14—S1	6.4 (8)
N1—C1—C2—C3	118.7 (6)	C16—N4—C15—N2	−88.9 (6)
N3—C1—C2—C3	−61.5 (7)	C19—N4—C15—N2	148.5 (5)
C1—C2—C3—C4	−178.0 (5)	C14—N2—C15—N4	107.8 (6)
C8—C2—C3—C4	57.1 (7)	N1—N2—C15—N4	−78.7 (6)
C7—C2—C3—C4	−60.2 (7)	C15—N4—C16—C17	175.9 (5)
C2—C3—C4—C5	62.4 (7)	C19—N4—C16—C17	−59.7 (6)
C2—C3—C4—C10	−59.2 (7)	C20—N5—C17—C16	168.3 (5)
C10—C4—C5—C6	58.4 (7)	C18—N5—C17—C16	−55.2 (7)
C3—C4—C5—C6	−62.7 (8)	N4—C16—C17—N5	57.9 (7)
C4—C5—C6—C11	−58.6 (7)	C20—N5—C18—C19	−165.7 (5)
C4—C5—C6—C7	61.4 (8)	C17—N5—C18—C19	57.2 (7)
C1—C2—C7—C6	179.7 (5)	C15—N4—C19—C18	−174.4 (5)
C8—C2—C7—C6	−56.5 (7)	C16—N4—C19—C18	60.4 (6)
C3—C2—C7—C6	61.2 (6)	N5—C18—C19—N4	−59.8 (7)
C11—C6—C7—C2	58.1 (8)	C17—N5—C20—C21	0.2 (8)
C5—C6—C7—C2	−62.1 (7)	C18—N5—C20—C21	−133.6 (6)
C1—C2—C8—C9	178.9 (5)	C17—N5—C20—C25	−176.0 (6)
C7—C2—C8—C9	57.6 (7)	C18—N5—C20—C25	50.2 (7)
C3—C2—C8—C9	−58.2 (7)	N5—C20—C21—C22	−175.6 (5)
C2—C8—C9—C10	59.9 (8)	C25—C20—C21—C22	0.6 (8)
C2—C8—C9—C11	−59.7 (8)	C20—C21—C22—C23	−2.1 (9)
C11—C9—C10—C4	58.0 (7)	C21—C22—C23—C24	1.3 (10)
C8—C9—C10—C4	−60.8 (8)	C22—C23—C24—C25	1.0 (10)
C5—C4—C10—C9	−58.6 (7)	C23—C24—C25—C20	−2.5 (10)
C3—C4—C10—C9	61.9 (8)	C21—C20—C25—C24	1.7 (9)
C5—C6—C11—C9	58.9 (7)	N5—C20—C25—C24	178.0 (6)
C7—C6—C11—C9	−59.6 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···S1i	0.97	2.90	3.836 (5)	162
C5—H5A···C20ii	0.97	2.80	3.750 (6)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯S1i	0.97	2.90	3.836 (5)	162
C5—H5A⋯C20ii	0.97	2.80	3.750 (6)	167

Symmetry codes: (i) ; (ii) .