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

In the title compound, C26H37N5S, the piperazine ring adopts a chair conformation with the exocyclic N-C bonds in pseudo-equatorial orientations. The piperazine ring (all atoms) subtends dihedral angles of 79.47 (9) and 73.07 (9)° with the triazole and benzene rings, respectively, resulting in an approximate U-shape for the mol-ecule. No significant inter-molecular inter-actions are observed in the crystal.

Related literature

For the pharmacological properties of adamantane derivatives and adamantyl-1,2,4-triazoles, see: Vernier et al. (1969 ▶); El-Emam et al. (2004 ▶, 2013 ▶); Al-Deeb et al. (2006 ▶); 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 ▶). For the synthesis of the starting material, see El-Emam & Ibrahim (1991 ▶). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H37N5S

M = 451.67

Triclinic,

a = 10.5618 (2) Å

b = 11.2123 (2) Å

c = 11.3084 (2) Å

α = 89.974 (1)°

β = 77.619 (1)°

γ = 70.842 (1)°

V = 1232.03 (4) Å3

Z = 2

Cu Kα radiation

μ = 1.33 mm−1

T = 296 K

0.69 × 0.51 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.460, T max = 0.626

13169 measured reflections

4319 independent reflections

3986 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.117

S = 1.08

4319 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813031127/hb7161sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031127/hb7161Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031127/hb7161Isup3.cml

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

C26H37N5S	Z = 2
Mr = 451.67	F(000) = 488
Triclinic, P1	Dx = 1.218 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 10.5618 (2) Å	Cell parameters from 6190 reflections
b = 11.2123 (2) Å	θ = 4.0–69.3°
c = 11.3084 (2) Å	µ = 1.33 mm−1
α = 89.974 (1)°	T = 296 K
β = 77.619 (1)°	Block, colourless
γ = 70.842 (1)°	0.69 × 0.51 × 0.39 mm
V = 1232.03 (4) Å3

Bruker APEXII CCD diffractometer	4319 independent reflections
Radiation source: fine-focus sealed tube	3986 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 67.5°, θmin = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.460, Tmax = 0.626	k = −13→13
13169 measured reflections	l = −12→10

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.2192P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
4319 reflections	Δρmax = 0.22 e Å−3
291 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (5)

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	0.22677 (5)	0.18527 (4)	0.13850 (5)	0.06851 (17)
N1	−0.34170 (12)	0.23635 (12)	0.02812 (11)	0.0489 (3)
N2	−0.16540 (13)	0.16685 (11)	0.19435 (11)	0.0477 (3)
N3	−0.03907 (13)	0.29271 (11)	0.26359 (12)	0.0486 (3)
N4	−0.13337 (13)	0.40759 (11)	0.31410 (11)	0.0485 (3)
N5	0.06528 (12)	0.42739 (11)	0.22592 (12)	0.0476 (3)
C1	−0.3188 (2)	0.16668 (18)	−0.27179 (17)	0.0688 (5)
H1A	−0.2913	0.0807	−0.2598	0.083*
C2	−0.2848 (2)	0.2056 (2)	−0.38571 (18)	0.0802 (6)
H2A	−0.2331	0.1456	−0.4498	0.096*
C3	−0.3260 (2)	0.3322 (2)	−0.40656 (17)	0.0704 (5)
H3A	−0.3028	0.3579	−0.4841	0.084*
C4	−0.4019 (2)	0.41987 (18)	−0.31105 (17)	0.0654 (4)
H4A	−0.4310	0.5056	−0.3240	0.078*
C5	−0.43506 (17)	0.38159 (17)	−0.19630 (16)	0.0599 (4)
H5A	−0.4859	0.4419	−0.1323	0.072*
C6	−0.39358 (15)	0.25397 (16)	−0.17470 (15)	0.0537 (4)
C7	−0.42804 (17)	0.21280 (18)	−0.04912 (16)	0.0594 (4)
H7A	−0.5240	0.2581	−0.0122	0.071*
H7B	−0.4154	0.1231	−0.0542	0.071*
C8	−0.39368 (16)	0.21841 (17)	0.15458 (15)	0.0567 (4)
H8A	−0.3900	0.1312	0.1624	0.068*
H8B	−0.4889	0.2726	0.1813	0.068*
C9	−0.30821 (16)	0.25001 (16)	0.23323 (15)	0.0560 (4)
H9A	−0.3131	0.3376	0.2266	0.067*
H9B	−0.3441	0.2393	0.3175	0.067*
C10	−0.11059 (15)	0.17746 (15)	0.06677 (14)	0.0524 (4)
H10A	−0.0178	0.1175	0.0415	0.063*
H10B	−0.1064	0.2620	0.0557	0.063*
C11	−0.20000 (16)	0.15135 (17)	−0.01097 (16)	0.0578 (4)
H11A	−0.1641	0.1624	−0.0951	0.069*
H11B	−0.1976	0.0643	−0.0054	0.069*
C12	−0.07720 (17)	0.17719 (14)	0.27078 (15)	0.0517 (4)
H12A	0.0066	0.1044	0.2506	0.062*
H12B	−0.1222	0.1729	0.3542	0.062*
C13	0.08395 (16)	0.30056 (14)	0.20895 (14)	0.0492 (3)
C14	0.17668 (16)	0.47676 (15)	0.17788 (17)	0.0597 (4)
H14A	0.2618	0.4197	0.1937	0.072*
H14B	0.1571	0.5583	0.2201	0.072*
C15	0.1955 (2)	0.49166 (19)	0.04371 (19)	0.0760 (5)
H15A	0.2609	0.5345	0.0186	0.114*
H15B	0.1090	0.5404	0.0264	0.114*
H15C	0.2287	0.4097	0.0006	0.114*
C16	−0.06822 (15)	0.48847 (13)	0.28983 (13)	0.0449 (3)
C17	−0.13467 (15)	0.62762 (13)	0.33107 (14)	0.0464 (3)
C18	−0.07200 (18)	0.66332 (15)	0.43095 (16)	0.0575 (4)
H18A	−0.0833	0.6123	0.4991	0.069*
H18B	0.0257	0.6464	0.3997	0.069*
C19	−0.1432 (2)	0.80408 (16)	0.47337 (18)	0.0678 (5)
H19A	−0.1015	0.8264	0.5357	0.081*
C20	−0.1263 (2)	0.88384 (16)	0.3662 (2)	0.0720 (5)
H20A	−0.1692	0.9730	0.3933	0.086*
H20B	−0.0292	0.8678	0.3323	0.086*
C21	−0.1921 (2)	0.85163 (16)	0.27002 (18)	0.0675 (5)
H21A	−0.1816	0.9042	0.2018	0.081*
C22	−0.3438 (2)	0.87674 (18)	0.3226 (2)	0.0792 (6)
H22A	−0.3861	0.8562	0.2608	0.095*
H22B	−0.3893	0.9657	0.3495	0.095*
C23	−0.36012 (19)	0.79624 (18)	0.4289 (2)	0.0737 (5)
H23A	−0.4583	0.8124	0.4628	0.088*
C24	−0.28947 (17)	0.65544 (16)	0.38466 (19)	0.0651 (5)
H24A	−0.3317	0.6342	0.3233	0.078*
H24B	−0.3014	0.6036	0.4520	0.078*
C25	−0.2958 (2)	0.82930 (19)	0.5263 (2)	0.0783 (6)
H25A	−0.3071	0.7784	0.5946	0.094*
H25B	−0.3409	0.9178	0.5550	0.094*
C26	−0.12118 (19)	0.71224 (15)	0.22511 (15)	0.0579 (4)
H26A	−0.0246	0.6969	0.1894	0.069*
H26B	−0.1627	0.6914	0.1630	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0597 (3)	0.0421 (2)	0.0933 (4)	−0.01144 (18)	−0.0046 (2)	−0.0041 (2)
N1	0.0435 (6)	0.0499 (7)	0.0504 (7)	−0.0141 (5)	−0.0069 (5)	0.0036 (5)
N2	0.0565 (7)	0.0367 (6)	0.0529 (7)	−0.0188 (5)	−0.0140 (5)	0.0067 (5)
N3	0.0568 (7)	0.0347 (6)	0.0569 (7)	−0.0198 (5)	−0.0113 (5)	0.0030 (5)
N4	0.0538 (7)	0.0387 (6)	0.0552 (7)	−0.0200 (5)	−0.0097 (5)	0.0024 (5)
N5	0.0475 (6)	0.0368 (6)	0.0607 (8)	−0.0178 (5)	−0.0112 (5)	0.0029 (5)
C1	0.0811 (12)	0.0559 (10)	0.0660 (11)	−0.0199 (9)	−0.0143 (9)	−0.0018 (8)
C2	0.1022 (15)	0.0737 (13)	0.0568 (11)	−0.0282 (11)	−0.0035 (10)	−0.0116 (9)
C3	0.0840 (12)	0.0775 (13)	0.0564 (10)	−0.0368 (10)	−0.0149 (9)	0.0063 (8)
C4	0.0700 (11)	0.0592 (10)	0.0710 (12)	−0.0235 (9)	−0.0213 (9)	0.0071 (8)
C5	0.0556 (9)	0.0596 (10)	0.0609 (10)	−0.0164 (8)	−0.0103 (7)	−0.0049 (7)
C6	0.0463 (8)	0.0607 (9)	0.0573 (9)	−0.0200 (7)	−0.0152 (6)	0.0018 (7)
C7	0.0519 (8)	0.0691 (11)	0.0614 (10)	−0.0258 (8)	−0.0132 (7)	0.0068 (8)
C8	0.0502 (8)	0.0644 (10)	0.0552 (9)	−0.0231 (7)	−0.0052 (7)	0.0060 (7)
C9	0.0550 (9)	0.0611 (10)	0.0500 (9)	−0.0230 (7)	−0.0024 (7)	0.0006 (7)
C10	0.0444 (7)	0.0501 (8)	0.0556 (9)	−0.0092 (6)	−0.0070 (6)	0.0005 (6)
C11	0.0489 (8)	0.0602 (10)	0.0550 (9)	−0.0087 (7)	−0.0072 (7)	−0.0058 (7)
C12	0.0667 (9)	0.0372 (7)	0.0594 (9)	−0.0247 (7)	−0.0200 (7)	0.0123 (6)
C13	0.0552 (8)	0.0384 (7)	0.0572 (9)	−0.0184 (6)	−0.0151 (7)	0.0047 (6)
C14	0.0478 (8)	0.0450 (8)	0.0874 (12)	−0.0212 (7)	−0.0089 (8)	0.0019 (7)
C15	0.0716 (11)	0.0614 (11)	0.0862 (14)	−0.0250 (9)	0.0045 (10)	0.0112 (9)
C16	0.0489 (7)	0.0374 (7)	0.0520 (8)	−0.0176 (6)	−0.0138 (6)	0.0041 (6)
C17	0.0483 (8)	0.0351 (7)	0.0580 (9)	−0.0152 (6)	−0.0145 (6)	0.0027 (6)
C18	0.0659 (10)	0.0455 (8)	0.0632 (10)	−0.0149 (7)	−0.0251 (8)	0.0019 (7)
C19	0.0816 (12)	0.0502 (9)	0.0746 (12)	−0.0187 (9)	−0.0292 (9)	−0.0094 (8)
C20	0.0787 (12)	0.0377 (8)	0.0997 (15)	−0.0230 (8)	−0.0151 (10)	−0.0030 (8)
C21	0.0830 (12)	0.0408 (9)	0.0741 (12)	−0.0137 (8)	−0.0196 (9)	0.0138 (8)
C22	0.0741 (12)	0.0502 (10)	0.1061 (16)	−0.0029 (9)	−0.0337 (11)	0.0037 (10)
C23	0.0524 (9)	0.0517 (10)	0.1044 (15)	−0.0100 (8)	−0.0034 (9)	−0.0068 (9)
C24	0.0525 (9)	0.0500 (9)	0.0910 (13)	−0.0194 (7)	−0.0088 (8)	−0.0014 (8)
C25	0.0895 (14)	0.0522 (10)	0.0762 (13)	−0.0130 (10)	−0.0006 (10)	−0.0086 (8)
C26	0.0698 (10)	0.0446 (8)	0.0587 (10)	−0.0164 (7)	−0.0180 (8)	0.0071 (7)

S1—C13	1.6694 (16)	C11—H11B	0.9700
N1—C8	1.457 (2)	C12—H12A	0.9700
N1—C11	1.4574 (19)	C12—H12B	0.9700
N1—C7	1.471 (2)	C14—C15	1.504 (3)
N2—C12	1.4299 (19)	C14—H14A	0.9700
N2—C10	1.455 (2)	C14—H14B	0.9700
N2—C9	1.460 (2)	C15—H15A	0.9600
N3—C13	1.345 (2)	C15—H15B	0.9600
N3—N4	1.3756 (17)	C15—H15C	0.9600
N3—C12	1.4746 (18)	C16—C17	1.5119 (19)
N4—C16	1.3037 (18)	C17—C18	1.539 (2)
N5—C13	1.3777 (18)	C17—C26	1.540 (2)
N5—C16	1.3817 (19)	C17—C24	1.542 (2)
N5—C14	1.463 (2)	C18—C19	1.534 (2)
C1—C2	1.372 (3)	C18—H18A	0.9700
C1—C6	1.382 (2)	C18—H18B	0.9700
C1—H1A	0.9300	C19—C20	1.520 (3)
C2—C3	1.378 (3)	C19—C25	1.523 (3)
C2—H2A	0.9300	C19—H19A	0.9800
C3—C4	1.374 (3)	C20—C21	1.512 (3)
C3—H3A	0.9300	C20—H20A	0.9700
C4—C5	1.376 (3)	C20—H20B	0.9700
C4—H4A	0.9300	C21—C22	1.515 (3)
C5—C6	1.390 (2)	C21—C26	1.527 (2)
C5—H5A	0.9300	C21—H21A	0.9800
C6—C7	1.500 (2)	C22—C23	1.518 (3)
C7—H7A	0.9700	C22—H22A	0.9700
C7—H7B	0.9700	C22—H22B	0.9700
C8—C9	1.512 (2)	C23—C25	1.516 (3)
C8—H8A	0.9700	C23—C24	1.539 (2)
C8—H8B	0.9700	C23—H23A	0.9800
C9—H9A	0.9700	C24—H24A	0.9700
C9—H9B	0.9700	C24—H24B	0.9700
C10—C11	1.513 (2)	C25—H25A	0.9700
C10—H10A	0.9700	C25—H25B	0.9700
C10—H10B	0.9700	C26—H26A	0.9700
C11—H11A	0.9700	C26—H26B	0.9700
C8—N1—C11	108.65 (12)	N5—C14—H14B	109.1
C8—N1—C7	110.90 (12)	C15—C14—H14B	109.1
C11—N1—C7	110.90 (13)	H14A—C14—H14B	107.8
C12—N2—C10	113.10 (12)	C14—C15—H15A	109.5
C12—N2—C9	114.96 (12)	C14—C15—H15B	109.5
C10—N2—C9	110.90 (12)	H15A—C15—H15B	109.5
C13—N3—N4	112.98 (11)	C14—C15—H15C	109.5
C13—N3—C12	126.34 (13)	H15A—C15—H15C	109.5
N4—N3—C12	120.67 (12)	H15B—C15—H15C	109.5
C16—N4—N3	104.98 (12)	N4—C16—N5	110.22 (12)
C13—N5—C16	108.38 (12)	N4—C16—C17	122.45 (13)
C13—N5—C14	120.92 (13)	N5—C16—C17	127.32 (12)
C16—N5—C14	130.70 (12)	C16—C17—C18	110.91 (12)
C2—C1—C6	120.65 (18)	C16—C17—C26	111.94 (13)
C2—C1—H1A	119.7	C18—C17—C26	109.46 (13)
C6—C1—H1A	119.7	C16—C17—C24	108.86 (12)
C1—C2—C3	120.97 (18)	C18—C17—C24	107.90 (14)
C1—C2—H2A	119.5	C26—C17—C24	107.63 (13)
C3—C2—H2A	119.5	C19—C18—C17	109.97 (13)
C4—C3—C2	118.94 (18)	C19—C18—H18A	109.7
C4—C3—H3A	120.5	C17—C18—H18A	109.7
C2—C3—H3A	120.5	C19—C18—H18B	109.7
C3—C4—C5	120.39 (18)	C17—C18—H18B	109.7
C3—C4—H4A	119.8	H18A—C18—H18B	108.2
C5—C4—H4A	119.8	C20—C19—C25	109.56 (16)
C4—C5—C6	120.91 (16)	C20—C19—C18	109.55 (15)
C4—C5—H5A	119.5	C25—C19—C18	109.49 (16)
C6—C5—H5A	119.5	C20—C19—H19A	109.4
C1—C6—C5	118.12 (16)	C25—C19—H19A	109.4
C1—C6—C7	121.14 (16)	C18—C19—H19A	109.4
C5—C6—C7	120.73 (15)	C21—C20—C19	109.95 (15)
N1—C7—C6	112.00 (13)	C21—C20—H20A	109.7
N1—C7—H7A	109.2	C19—C20—H20A	109.7
C6—C7—H7A	109.2	C21—C20—H20B	109.7
N1—C7—H7B	109.2	C19—C20—H20B	109.7
C6—C7—H7B	109.2	H20A—C20—H20B	108.2
H7A—C7—H7B	107.9	C20—C21—C22	109.80 (17)
N1—C8—C9	110.02 (13)	C20—C21—C26	109.38 (14)
N1—C8—H8A	109.7	C22—C21—C26	109.75 (16)
C9—C8—H8A	109.7	C20—C21—H21A	109.3
N1—C8—H8B	109.7	C22—C21—H21A	109.3
C9—C8—H8B	109.7	C26—C21—H21A	109.3
H8A—C8—H8B	108.2	C21—C22—C23	109.30 (15)
N2—C9—C8	109.63 (13)	C21—C22—H22A	109.8
N2—C9—H9A	109.7	C23—C22—H22A	109.8
C8—C9—H9A	109.7	C21—C22—H22B	109.8
N2—C9—H9B	109.7	C23—C22—H22B	109.8
C8—C9—H9B	109.7	H22A—C22—H22B	108.3
H9A—C9—H9B	108.2	C25—C23—C22	109.94 (17)
N2—C10—C11	110.69 (13)	C25—C23—C24	109.75 (16)
N2—C10—H10A	109.5	C22—C23—C24	109.33 (17)
C11—C10—H10A	109.5	C25—C23—H23A	109.3
N2—C10—H10B	109.5	C22—C23—H23A	109.3
C11—C10—H10B	109.5	C24—C23—H23A	109.3
H10A—C10—H10B	108.1	C23—C24—C17	110.23 (14)
N1—C11—C10	110.90 (13)	C23—C24—H24A	109.6
N1—C11—H11A	109.5	C17—C24—H24A	109.6
C10—C11—H11A	109.5	C23—C24—H24B	109.6
N1—C11—H11B	109.5	C17—C24—H24B	109.6
C10—C11—H11B	109.5	H24A—C24—H24B	108.1
H11A—C11—H11B	108.0	C23—C25—C19	109.13 (16)
N2—C12—N3	116.03 (12)	C23—C25—H25A	109.9
N2—C12—H12A	108.3	C19—C25—H25A	109.9
N3—C12—H12A	108.3	C23—C25—H25B	109.9
N2—C12—H12B	108.3	C19—C25—H25B	109.9
N3—C12—H12B	108.3	H25A—C25—H25B	108.3
H12A—C12—H12B	107.4	C21—C26—C17	110.28 (14)
N3—C13—N5	103.43 (13)	C21—C26—H26A	109.6
N3—C13—S1	128.88 (11)	C17—C26—H26A	109.6
N5—C13—S1	127.69 (12)	C21—C26—H26B	109.6
N5—C14—C15	112.60 (15)	C17—C26—H26B	109.6
N5—C14—H14A	109.1	H26A—C26—H26B	108.1
C15—C14—H14A	109.1
C13—N3—N4—C16	0.40 (16)	N3—N4—C16—C17	−179.14 (13)
C12—N3—N4—C16	−178.80 (13)	C13—N5—C16—N4	0.30 (17)
C6—C1—C2—C3	−1.0 (3)	C14—N5—C16—N4	179.45 (15)
C1—C2—C3—C4	0.2 (3)	C13—N5—C16—C17	178.95 (14)
C2—C3—C4—C5	0.5 (3)	C14—N5—C16—C17	−1.9 (3)
C3—C4—C5—C6	−0.5 (3)	N4—C16—C17—C18	109.96 (16)
C2—C1—C6—C5	1.1 (3)	N5—C16—C17—C18	−68.55 (19)
C2—C1—C6—C7	−178.28 (18)	N4—C16—C17—C26	−127.47 (15)
C4—C5—C6—C1	−0.3 (3)	N5—C16—C17—C26	54.03 (19)
C4—C5—C6—C7	179.02 (15)	N4—C16—C17—C24	−8.6 (2)
C8—N1—C7—C6	169.20 (14)	N5—C16—C17—C24	172.88 (15)
C11—N1—C7—C6	−69.99 (18)	C16—C17—C18—C19	−178.70 (14)
C1—C6—C7—N1	104.19 (18)	C26—C17—C18—C19	57.30 (18)
C5—C6—C7—N1	−75.16 (19)	C24—C17—C18—C19	−59.55 (18)
C11—N1—C8—C9	60.95 (17)	C17—C18—C19—C20	−58.9 (2)
C7—N1—C8—C9	−176.91 (14)	C17—C18—C19—C25	61.3 (2)
C12—N2—C9—C8	−172.94 (12)	C25—C19—C20—C21	−59.28 (19)
C10—N2—C9—C8	57.20 (16)	C18—C19—C20—C21	60.8 (2)
N1—C8—C9—N2	−60.32 (17)	C19—C20—C21—C22	59.44 (19)
C12—N2—C10—C11	173.70 (12)	C19—C20—C21—C26	−61.1 (2)
C9—N2—C10—C11	−55.46 (16)	C20—C21—C22—C23	−59.6 (2)
C8—N1—C11—C10	−59.08 (18)	C26—C21—C22—C23	60.7 (2)
C7—N1—C11—C10	178.79 (13)	C21—C22—C23—C25	60.2 (2)
N2—C10—C11—N1	56.68 (18)	C21—C22—C23—C24	−60.4 (2)
C10—N2—C12—N3	55.67 (17)	C25—C23—C24—C17	−60.1 (2)
C9—N2—C12—N3	−73.11 (17)	C22—C23—C24—C17	60.5 (2)
C13—N3—C12—N2	−105.86 (17)	C16—C17—C24—C23	179.36 (15)
N4—N3—C12—N2	73.21 (18)	C18—C17—C24—C23	58.92 (19)
N4—N3—C13—N5	−0.21 (16)	C26—C17—C24—C23	−59.11 (19)
C12—N3—C13—N5	178.92 (13)	C22—C23—C25—C19	−60.1 (2)
N4—N3—C13—S1	179.12 (11)	C24—C23—C25—C19	60.2 (2)
C12—N3—C13—S1	−1.7 (2)	C20—C19—C25—C23	59.33 (19)
C16—N5—C13—N3	−0.04 (16)	C18—C19—C25—C23	−60.8 (2)
C14—N5—C13—N3	−179.29 (14)	C20—C21—C26—C17	59.6 (2)
C16—N5—C13—S1	−179.39 (12)	C22—C21—C26—C17	−60.88 (19)
C14—N5—C13—S1	1.4 (2)	C16—C17—C26—C21	178.81 (13)
C13—N5—C14—C15	77.74 (18)	C18—C17—C26—C21	−57.80 (18)
C16—N5—C14—C15	−101.32 (19)	C24—C17—C26—C21	59.22 (18)
N3—N4—C16—N5	−0.41 (15)