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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2013 Nov 23;69(Pt 12):o1813–o1814. doi: 10.1107/S1600536813031127

3-(Adamantan-1-yl)-1-[(4-benzyl­piperazin-1-yl)meth­yl]-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

Ebtehal S Al-Abdullah a, Hanaa M Al-Tuwaijri a, Ali A El-Emam a,‡, C S Chidan Kumar b, Hoong-Kun Fun a,*,§
PMCID: PMC3885067  PMID: 24454243

Abstract

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 mol­ecule. No significant inter­molecular inter­actions 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 ▶).graphic file with name e-69-o1813-scheme1.jpg

Experimental  

Crystal data  

  • C26H37N5S

  • M r = 451.67

  • Triclinic, Inline graphic

  • 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: SAINT (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 ▶).

Supplementary Material

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

e-69-o1813-sup1.cif (35KB, cif)

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

e-69-o1813-Isup2.hkl (211.6KB, hkl)
Click here for additional data file. (9.9KB, cml)

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

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

Acknowledgments

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

supplementary crystallographic information

1. Comment

Adamantane derivatives were early recognized for their diverse biological activities including antiviral activity against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al., 2004). In addition, adamantane derivatives were reported to exhibit marked antibacterial (Kadi et al., 2007, 2010) and anti-inflammatory (El-Emam & Ibrahim, 1991) activities. In continuation of our interest in this area, we now describe the synthesis and structure of the title compound, (I).

The piperazine ring (N1/N2/C8–C11) ring, Fig. 1, adopts a chair conformation, with puckering parameters: Q = 0.5829 (17) Å, θ = 176.42 (17)°, and φ = 221 (3)° (Cremer & Pople, 1975) and a maximum deviation of 0.257 (1) Å at atom N1. The dihedral angle between the piperazine ring and the triazole (N3–N5/C13/C16) ring is 79.47 (9)°. The triazole (N3–N5/C13/C16) ring forms the dihedral angle of 53.07 (10)° with the benzene (C1–C6) ring. In the crystal, no significant intermolecular interactions beyond the expected packing contacts are observed.

2. Experimental

A mixture of 527 mg (2 mmol) of 3-(1-adamantyl)-4-ethyl-4H-1,2,4- triazole-5-thiol (El-Emam et al., 1991), 1-benzylpiperazine (353 mg, 2 mmol) and 37% formaldehyde solution (1 ml), in ethanol (8 ml), was heated under reflux for 15 min until a clear solution was obtained. Stirring was continued for 12 h at room temperature and the mixture was allowed to stand overnight. Cold water (5 ml) was slowly added and the mixture was stirred for 20 min. The precipitated crude product were filtered, washed with water, dried, and crystallized from ethanol to yield 759 mg (84%) of the title compound (C26H37N5S) as crystals. m.p.: 441–443 K. Single crystals suitable for X-ray analysis were recrystallized from CHCl3:EtOH solution (1:1; 5 ml) through slow evaporation at room temperature.

1H NMR (CDCl3, 500.13 MHz): δ 1.13 (t, 3H, CH2CH3, J = 6.0 Hz), 1.68–1.73 (m, 6H, Adamantane-H), 1.98–2.10 (m, 9H, Adamantane-H), 2.72–2.76 (m, 4H, Piperazine-H), 3.24–3.26 (m, 4H, Piperazine-H), 3.72 (s, 2H, Benzylic-CH2), 4.15 (q, 2H, CH2CH3, J = 6.5 Hz), 5.02 (s, 2H, CH2), 7.20–7.54 (m, 5H, Ar—H). 13C NMR (CDCl3, 125.76 MHz): δ 12.74 (CH2CH3), 26.90, 34.36, 35.26, 38.82 (Adamantane-C), 40.62 (CH2CH3), 46.01, 50.37 (Piperazine-C), 61.59 (Benzylic-CH2), 66.66 (CH2), 127.40, 128.31, 129.19, 130.57 (Ar—C), 155.55 (Triazole C-5), 167.73 (C=S).

3. Refinement

All H atoms were positioned geometrically [C—H = 0.93, 0.96, 0.97 or 0.98 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5(methyl group)Ueq(C).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound with 30% probability displacement ellipsoids.

Crystal data

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
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Data collection

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
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Refinement

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)
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Special details

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

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, º)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7161).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-69-o1813-sup1.cif (35KB, cif)

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

e-69-o1813-Isup2.hkl (211.6KB, hkl)
Click here for additional data file. (9.9KB, cml)

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

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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