organic papers
Acta Cryst.(2005). E61, o2679–o2681 doi:10.1107/S1600536805022828 Ariyananda and Norman C
24H25N5"+2ClO4
o2679
Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
2-{[
N
-(Pyridinium-2-ylmethyl)-
N
-(pyridin-2-yl-
methyl)amino]methyl}-1-(pyridin-2-ylmethyl)-pyridinium diperchlorate
L. Mihiri D. Ariyanandaaand Richard E. Normana,b*
a
Chemistry Department, CNSB-210, University of Louisiana at Monroe, LA 71209, USA, and
bDepartment of Chemistry, Box 2117, Sam
Houston State University, Huntsville, TX 77341, USA
Correspondence e-mail: norman@shsu.edu
Key indicators
Single-crystal X-ray study
T= 100 K
Mean(C–C) = 0.005 A˚ Disorder in main residue
Rfactor = 0.073
wRfactor = 0.161
Data-to-parameter ratio = 13.5
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
The cation of the title salt, C24H25N5 2+
2ClO4
, contains a tris(2-pyridylmethyl)amine core in which one of the pyridine N atoms is protonated and a second pyridine N atom forms an additional C—N bond to another 2-pyridylmethyl group, resulting in a second pyridinium center. The protonated pyridinium hydrogen bonds to a pyridine ring of a neighboring dication. The hydrogen-bonded H atom is disordered between the two N atoms.
Comment
During an attempt to prepare an MnII tpa complex [tpa is tris(2-pyridylmethyl)amine] by reacting manganese(II) chloride tetrahydrate with H3tpa(ClO4)3and triethylamine in
methanol, the title compound was produced. The preparation of [Mn(tpa)Cl2] has been reported (Allenet al., 1995) under a
nitrogen atmosphere, but the structure has not been reported. So far, our attempts to prepare the title compound, (I), under metal-free conditions by reaction of 2-picolylchloride hydro-chloride with tpa [produced by in situ deprotonation of H3tpa(ClO4)3] have been unsuccessful.
The structure of (I) consists of two perchlorate anions (which have typical distances and angles) and a dication, shown in Fig. 1. The dication contains a tpa core structure in which two of the pyridine N atoms share a proton and a third pyridine N atom forms an additional C—N bond to another 2-pyridylmethyl group, resulting in a second pyridinium center. There is a hydrogen bond between the partially protonated pyridinium N atom of one dication and the pyridine N atom of an adjacent molecule [the N2 N3iseparation is 2.706 (3) A˚ ; see Fig. 2; symmetry code as in Table 2]. The H atom is disordered across the hydrogen bond. Thus, in the tpa core,
two of the pyridine rings are half protonated and the third is alkylated.
There are no obvious trends in the distances and angles of the various pyridine rings in (I), and the values are typical of
other tpa structures (e.g. Britton et al., 1991; Hazell et al., 1999). The distances and angles of the ‘extra’ 2-pyridylmethyl group are also typical.
Experimental
Triethylamine (0.1513 g, 1.495 mmol) and H3tpa(ClO4)3 (0.2956 g,
0.4995 mmol) were dissolved in methanol (20 ml). Manganese(II) chloride tetrahydrate (0.0989 g, 0.500 mmol) was added with stirring, producing a clear yellow solution. Colorless crystals formed after a few days. M.p. 445–449 K.1H NMR (300 MHz, D
2O): 4.07 (6H), 5.91
(2H), 7.22 (d, 1H), 7.34 (t, 1H), 7.47 (t, 2H), 7.54 (d, 2H), 7.81 (t, 1H), 7.89 (t, 1H), 7.97 (t, 2H), 8.19 (d, 1H), 8.24 (d, 1H), 8.44 (d, 2H), 8.48 (d,1H), 8.70 (d, 1H).
Crystal data
C24H25N52+2ClO4
Mr= 582.40 Monoclinic,P21=c a= 13.9313 (2) A˚
b= 10.9888 (2) A˚
c= 18.1280 (4) A˚ = 108.0650 (8) V= 2638.38 (8) A˚3
Z= 4
Dx= 1.466 Mg m
3
MoKradiation Cell parameters from 8603
reflections = 2.5–32.0
= 0.30 mm1
T= 100 K Prism, colorless 0.200.120.10 mm
Data collection
Nonius KappaCCD diffractometer !scans withoffsets
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor 1997)
Tmin= 0.869,Tmax= 0.955
48722 measured reflections
9091 independent reflections 4740 reflections withI> 2(I)
Rint= 0.055 max= 32.1
h=20!20
k=16!13
l=26!25
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.073
wR(F2) = 0.161
S= 0.94 4740 reflections 352 parameters
H-atom parameters constrained
w= 1/[2
(Fo) + 0.003025|Fo|2]
(/)max< 0.001
max= 0.77 e A˚
3
min=0.56 e A˚
3
Table 1
Selected geometric parameters (A˚ ,).
N1—C6 1.462 (3)
N1—C12 1.472 (3)
N1—C24 1.462 (3)
N2—C1 1.339 (4)
N2—C5 1.349 (4)
N3—C7 1.350 (4)
N3—C11 1.351 (3)
N4—C13 1.360 (4)
N4—C17 1.338 (4)
N5—C18 1.480 (4)
N5—C19 1.360 (3)
N5—C23 1.351 (3)
C6—N1—C12 111.1 (2) C6—N1—C24 110.2 (2) C12—N1—C24 110.0 (2) C1—N2—C5 119.1 (2) C7—N3—C11 121.6 (2) C13—N4—C17 116.3 (3) C18—N5—C19 118.2 (2) C18—N5—C23 121.1 (2) C19—N5—C23 120.7 (2) N2—C1—C2 122.0 (3) N2—C5—C4 121.4 (2) N2—C5—C6 116.2 (2) N1—C6—C5 112.7 (2)
N3—C7—C8 121.1 (3) N3—C11—C10 119.1 (2) N3—C11—C12 117.3 (2) N1—C12—C11 111.2 (2) N4—C13—C14 123.8 (4) N4—C17—C16 123.8 (3) N4—C17—C18 117.3 (3) N5—C18—C17 112.1 (2) N5—C19—C20 121.3 (3) N5—C23—C22 119.4 (2) N5—C23—C24 117.3 (2) N1—C24—C23 112.8 (2)
organic papers
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Ariyananda and Norman C24H25N5"+2ClO4 Acta Cryst.(2005). E61, o2679–o2681 Figure 2
[image:2.610.46.293.71.348.2] [image:2.610.46.295.404.639.2]A view of two dications of (I), showing the hydrogen bonding. The disordered H atoms, bound to N2 and N3, are shown in violet. The prime corresponds to symmetry code (i) in Table 2.
Figure 1
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N2—H1 N3i
0.95 1.79 2.706 (3) 162
Symmetry code: (i)x;y;zþ1.
Atom H1, the H atom associated with N2, was found in a differ-ence map, and then placed in a calculated position. During subse-quent refinement, atom H26, the H atom associated with N3, was observed in a difference map. Atoms N2 and N3 are the hydrogen-bonded pair of N atoms. Consequently, both H atoms were placed in calculated positions with half occupancy, and assigned displacement parameters 0.6 times those of N2 and N3 (N—H = 0.95 A˚ ). All of the other H atoms were assigned displacement parameters 1.2 times those of the atoms to which they are bound and were treated as riding in idealized positions (C—H = 0.95 A˚ ). The perchlorate anions are probably disordered, as reflected by the large displacement para-meters. Attempts were made to model this disorder with various O atoms with partial occupancy, but the resulting models produced unreasonable distances and angles. The current model is reasonably well behaved and the Cl—O distances fall in the range 1.427 (3)– 1.429 (3) A˚ for Cl1, and 1.391 (3)–1.444 (4) A˚ for Cl2.
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction:
SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure:SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN for Windows (Mol-ecular Structure Corporation, 1999); mol(Mol-ecular graphics:ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSANfor Windows.
We thank Frank Fronczek for data collection and the Louisiana Board of Regents Support Fund for financial support.
References
Allen, C. S., Chuang, C.-L., Cornebise, M. & Canary, J. W. (1995).Inorg. Chim. Acta,239, 29–37.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993).J. Appl. Cryst.26, 343–350.
Britton, D., Norman, R. E. & Que, L. Jr (1991).Acta Cryst. C47, 2415– 2417.
Hazell, A., McGinley, J. & Toftlund, H. (1999).J. Chem. Soc. Dalton Trans.
pp. 1271–1276.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Molecular Structure Corporation (1999). TEXSAN for Windows. Version 1.06. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA. Nonius (2000).COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
organic papers
Acta Cryst.(2005). E61, o2679–o2681 Ariyananda and Norman C
supporting information
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Acta Cryst. (2005). E61, o2679–o2681
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Acta Cryst. (2005). E61, o2679–o2681 [https://doi.org/10.1107/S1600536805022828]
2-{[
N
-(Pyridinium-2-ylmethyl)-
N
-(pyridin-2-ylmethyl)amino]-methyl}-1-(pyridin-2-ylmethyl)pyridinium diperchlorate
L. Mihiri D. Ariyananda and Richard E. Norman
(I)
Crystal data
C24H25N52+·2ClO4−
Mr = 582.40
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 13.9313 (2) Å
b = 10.9888 (2) Å
c = 18.1280 (4) Å
β = 108.0650 (8)°
V = 2638.38 (8) Å3
Z = 4
F(000) = 1208
Dx = 1.466 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 8603 reflections
θ = 2.5–32.0°
µ = 0.30 mm−1
T = 100 K Prism, colorless 0.20 × 0.12 × 0.10 mm
Data collection
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans with κ offsets
Absorption correction: multi-scan
(SCALEPACK: Otwinowski & Minor 1997)
Tmin = 0.869, Tmax = 0.955
48722 measured reflections 9091 independent reflections 4740 reflections with I > 2σ(I)
Rint = 0.055
θmax = 32.1°, θmin = 3.0°
h = 0→20
k = 0→16
l = −26→25
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.073
wR(F2) = 0.161
S = 0.94 4740 reflections 352 parameters 0 restraints
0 constraints
H-atom parameters constrained
Weighting scheme based on measured s.u.'s w = 1/[σ2(F
o) + 0.003025|Fo|2]
(Δ/σ)max = 0.0003
Δρmax = 0.77 e Å−3
Δρmin = −0.57 e Å−3
Special details
Refinement. Refinement of F2. The weighted R-factor wR and goodness of fit are based on F2, conventional R-factors R
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Acta Cryst. (2005). E61, o2679–o2681
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq Occ. (<1)
Cl1 −0.04650 (6) −0.13051 (7) 0.27292 (4) 0.0341 (2) Cl2 0.36495 (6) 0.49562 (7) 0.62091 (4) 0.0348 (2) O1 −0.0774 (2) −0.2542 (3) 0.2573 (2) 0.0725 (9) O2 −0.1317 (2) −0.0509 (3) 0.2500 (2) 0.0795 (11) O3 0.0072 (2) −0.1158 (2) 0.35351 (12) 0.0430 (7) O4 0.0189 (2) −0.1000 (2) 0.22868 (12) 0.0400 (6) O5 0.3658 (3) 0.3683 (2) 0.6332 (2) 0.0742 (10) O6 0.4090 (3) 0.5282 (3) 0.5646 (2) 0.110 (1) O7 0.4136 (2) 0.5569 (2) 0.69111 (12) 0.0329 (6) O8 0.2608 (2) 0.5344 (4) 0.5979 (3) 0.1162 (13) N1 0.1388 (2) 0.1485 (2) 0.47253 (13) 0.0208 (6) N2 0.2301 (2) −0.1106 (2) 0.5972 (1) 0.0245 (6) N3 −0.0915 (2) 0.2702 (2) 0.48744 (13) 0.0235 (6) N4 0.3828 (2) −0.0465 (3) 0.3983 (2) 0.0391 (8) N5 0.2789 (2) 0.1525 (2) 0.32925 (13) 0.0223 (6) C1 0.3145 (2) −0.1546 (3) 0.6479 (2) 0.0332 (8) C2 0.3978 (2) −0.0822 (3) 0.6811 (2) 0.0377 (9) C3 0.3947 (2) 0.0393 (3) 0.6608 (2) 0.0322 (8) C4 0.3069 (2) 0.0852 (3) 0.6091 (2) 0.0272 (7) C5 0.2255 (2) 0.0086 (2) 0.5784 (2) 0.0206 (6) C6 0.1266 (2) 0.0532 (2) 0.5253 (2) 0.0203 (6) C7 −0.1304 (2) 0.3317 (3) 0.5360 (2) 0.0290 (8) C8 −0.0715 (2) 0.4091 (3) 0.5916 (2) 0.0293 (8) C9 0.0295 (2) 0.4210 (3) 0.5961 (2) 0.0275 (7) C10 0.0685 (2) 0.3580 (2) 0.5466 (2) 0.0249 (7) C11 0.0066 (2) 0.2812 (2) 0.4915 (2) 0.0214 (6) C12 0.0421 (2) 0.2095 (2) 0.4343 (2) 0.0231 (7) C13 0.4319 (2) −0.1436 (4) 0.4395 (2) 0.0493 (11) C14 0.4052 (3) −0.2620 (4) 0.4205 (3) 0.0536 (12) C15 0.3228 (3) −0.2851 (3) 0.3571 (3) 0.0538 (12) C16 0.2687 (3) −0.1889 (3) 0.3141 (2) 0.0452 (10) C17 0.3028 (2) −0.0716 (3) 0.3367 (2) 0.0310 (8) C18 0.2483 (2) 0.0349 (3) 0.2889 (2) 0.0273 (7) C19 0.3424 (2) 0.2254 (3) 0.3053 (2) 0.0301 (8) C20 0.3784 (2) 0.3312 (3) 0.3427 (2) 0.0347 (8) C21 0.3502 (2) 0.3636 (3) 0.4063 (2) 0.0306 (8) C22 0.2835 (2) 0.2913 (3) 0.4295 (2) 0.0255 (7) C23 0.2487 (2) 0.1842 (2) 0.3906 (2) 0.0206 (6) C24 0.1799 (2) 0.0971 (3) 0.4143 (2) 0.0261 (7)
H1 0.1741 −0.1625 0.5746 0.015* 0.5
H2 0.3172 −0.2383 0.6616 0.040*
H3 0.4565 −0.1155 0.7174 0.045*
H4 0.4517 0.0903 0.6820 0.039*
H5 0.3026 0.1687 0.5948 0.033*
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H7 0.0918 −0.0134 0.4953 0.024*
H8 −0.1996 0.3213 0.5318 0.035*
H9 −0.0990 0.4527 0.6256 0.035*
H10 0.0720 0.4735 0.6339 0.033*
H11 0.1376 0.3669 0.5501 0.030*
H12 −0.0073 0.1498 0.4107 0.028*
H13 0.0504 0.2631 0.3956 0.028*
H14 0.4882 −0.1284 0.4841 0.059*
H15 0.4429 −0.3268 0.4505 0.064*
H16 0.3027 −0.3666 0.3428 0.065*
H17 0.2106 −0.2028 0.2707 0.054*
H18 0.2633 0.0365 0.2412 0.033*
H19 0.1777 0.0245 0.2789 0.033*
H20 0.3619 0.2020 0.2615 0.036*
H21 0.4223 0.3817 0.3253 0.042*
H22 0.3764 0.4357 0.4343 0.037*
H23 0.2617 0.3153 0.4721 0.031*
H24 0.1255 0.0763 0.3697 0.031*
H25 0.2171 0.0258 0.4351 0.031*
H26 −0.1341 0.2180 0.4495 0.014* 0.5
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
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Acta Cryst. (2005). E61, o2679–o2681
C10 0.0265 (13) 0.0226 (13) 0.023 (2) −0.0014 (11) 0.0034 (11) 0.0014 (11) C11 0.0277 (13) 0.0186 (12) 0.018 (1) −0.0001 (10) 0.0071 (10) 0.0033 (10) C12 0.0279 (13) 0.0232 (13) 0.018 (1) −0.0037 (11) 0.0064 (11) 0.0017 (11) C13 0.034 (2) 0.056 (2) 0.055 (2) 0.009 (2) 0.009 (2) 0.020 (2) C14 0.051 (2) 0.044 (2) 0.070 (3) 0.019 (2) 0.026 (2) 0.024 (2) C15 0.071 (3) 0.034 (2) 0.063 (3) 0.008 (2) 0.031 (2) 0.007 (2) C16 0.057 (2) 0.036 (2) 0.044 (2) 0.005 (2) 0.018 (2) −0.005 (2) C17 0.031 (2) 0.035 (2) 0.033 (2) 0.0073 (13) 0.0198 (13) 0.0026 (13) C18 0.029 (1) 0.032 (1) 0.022 (2) 0.0012 (12) 0.0106 (12) −0.0039 (12) C19 0.0243 (13) 0.043 (2) 0.026 (2) 0.0010 (12) 0.0131 (12) 0.0060 (13) C20 0.027 (1) 0.043 (2) 0.035 (2) −0.0096 (13) 0.0119 (13) 0.008 (1) C21 0.030 (1) 0.031 (2) 0.029 (2) −0.0099 (12) 0.0066 (12) 0.0024 (13) C22 0.0294 (13) 0.028 (1) 0.021 (1) −0.0054 (11) 0.0098 (11) 0.0014 (11) C23 0.0190 (11) 0.0245 (13) 0.0178 (13) −0.0013 (10) 0.0052 (10) 0.0026 (10) C24 0.031 (1) 0.0261 (13) 0.026 (2) −0.0065 (11) 0.0163 (12) −0.0062 (12)
Geometric parameters (Å, º)
Cl1—O1 1.427 (3) C16—C17 1.391 (5)
Cl1—O2 1.429 (3) C17—C18 1.513 (4)
Cl1—O3 1.429 (2) C19—C20 1.362 (4)
Cl1—O4 1.428 (2) C20—C21 1.375 (4)
Cl2—O5 1.417 (3) C21—C22 1.383 (4)
Cl2—O6 1.391 (3) C22—C23 1.381 (4)
Cl2—O7 1.413 (2) C23—C24 1.508 (4)
Cl2—O8 1.444 (4) N2—H1 0.950
N1—C6 1.462 (3) C1—H2 0.950
N1—C12 1.472 (3) C2—H3 0.950
N1—C24 1.462 (3) C3—H4 0.950
N2—C1 1.339 (4) C4—H5 0.950
N2—C5 1.349 (4) C6—H6 0.950
N3—C7 1.350 (4) C6—H7 0.950
N3—C11 1.351 (3) C7—H8 0.950
N4—C13 1.360 (4) C8—H9 0.950
N4—C17 1.338 (4) C9—H10 0.950
N5—C18 1.480 (4) C10—H11 0.950
N5—C19 1.360 (3) C12—H12 0.950
N5—C23 1.351 (3) C12—H13 0.950
C1—C2 1.382 (5) C13—H14 0.950
C2—C3 1.381 (5) C14—H15 0.950
C3—C4 1.385 (4) C15—H16 0.950
C4—C5 1.383 (4) C16—H17 0.950
C5—C6 1.498 (4) C18—H18 0.950
C7—C8 1.378 (4) C18—H19 0.950
C8—C9 1.390 (4) C19—H20 0.950
C9—C10 1.372 (4) C20—H21 0.950
C10—C11 1.385 (4) C21—H22 0.950
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C13—C14 1.367 (6) C24—H24 0.950
C14—C15 1.373 (6) C24—H25 0.950
C15—C16 1.388 (5) N3—H26 0.950
O1···N5i 2.943 (3) O8···C7ii 2.938 (5)
O1—Cl1—O2 110.7 (2) C7—N3—H26 119.2
O1—Cl1—O3 110.0 (2) C11—N3—H26 119.2
O1—Cl1—O4 108.5 (2) N2—C1—H2 119.0
O2—Cl1—O3 110.6 (2) C2—C1—H2 119.0
O2—Cl1—O4 108.0 (2) C1—C2—H3 120.4
O3—Cl1—O4 108.9 (1) C3—C2—H3 120.4
O5—Cl2—O6 112.7 (2) C2—C3—H4 120.6
O5—Cl2—O7 110.5 (2) C4—C3—H4 120.6
O5—Cl2—O8 107.2 (2) C3—C4—H5 120.3
O6—Cl2—O7 109.9 (2) C5—C4—H5 120.3
O6—Cl2—O8 110.2 (3) N1—C6—H6 108.7
O7—Cl2—O8 106.1 (2) N1—C6—H7 108.7
C6—N1—C12 111.1 (2) C5—C6—H6 108.7
C6—N1—C24 110.2 (2) C5—C6—H7 108.7
C12—N1—C24 110.0 (2) H6—C6—H7 109.5
C1—N2—C5 119.1 (2) N3—C7—H8 119.4
C7—N3—C11 121.6 (2) C8—C7—H8 119.4
C13—N4—C17 116.3 (3) C7—C8—H9 121.2
C18—N5—C19 118.2 (2) C9—C8—H9 121.2
C18—N5—C23 121.1 (2) C8—C9—H10 119.6
C19—N5—C23 120.7 (2) C10—C9—H10 119.6
N2—C1—C2 122.0 (3) C9—C10—H11 120.2
C1—C2—C3 119.2 (3) C11—C10—H11 120.2
C2—C3—C4 118.7 (3) N1—C12—H12 109.0
C3—C4—C5 119.5 (3) N1—C12—H13 109.0
N2—C5—C4 121.4 (2) C11—C12—H12 109.0
N2—C5—C6 116.2 (2) C11—C12—H13 109.0
C4—C5—C6 122.4 (2) H12—C12—H13 109.5
N1—C6—C5 112.7 (2) N4—C13—H14 118.1
N3—C7—C8 121.1 (3) C14—C13—H14 118.1
C7—C8—C9 117.6 (3) C13—C14—H15 120.7
C8—C9—C10 120.9 (3) C15—C14—H15 120.7
C9—C10—C11 119.7 (2) C14—C15—H16 120.1
N3—C11—C10 119.1 (2) C16—C15—H16 120.1
N3—C11—C12 117.3 (2) C15—C16—H17 121.2
C10—C11—C12 123.6 (2) C17—C16—H17 121.2
N1—C12—C11 111.2 (2) N5—C18—H18 108.8
N4—C13—C14 123.8 (4) N5—C18—H19 108.8
C13—C14—C15 118.6 (3) C17—C18—H18 108.8
C14—C15—C16 119.8 (4) C17—C18—H19 108.8
C15—C16—C17 117.6 (4) H18—C18—H19 109.5
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N4—C17—C18 117.3 (3) C20—C19—H20 119.4
C16—C17—C18 118.9 (3) C19—C20—H21 120.6
N5—C18—C17 112.1 (2) C21—C20—H21 120.6
N5—C19—C20 121.3 (3) C20—C21—H22 120.0
C19—C20—C21 118.8 (3) C22—C21—H22 120.0
C20—C21—C22 120.0 (3) C21—C22—H23 120.1
C21—C22—C23 119.8 (3) C23—C22—H23 120.1
N5—C23—C22 119.4 (2) N1—C24—H24 108.6
N5—C23—C24 117.3 (2) N1—C24—H25 108.6
C22—C23—C24 123.2 (2) C23—C24—H24 108.6
N1—C24—C23 112.8 (2) C23—C24—H25 108.6
C1—N2—H1 120.4 H24—C24—H25 109.5
C5—N2—H1 120.4
N1—C6—C5—N2 −145.6 (2) C7—N3—C11—C10 −0.4 (4) N1—C6—C5—C4 36.6 (3) C7—N3—C11—C12 −179.5 (2) N1—C12—C11—N3 −134.6 (2) C7—C8—C9—C10 0.2 (4) N1—C12—C11—C10 46.3 (3) C8—C7—N3—C11 0.5 (4) N1—C24—C23—N5 −170.6 (2) C8—C9—C10—C11 −0.1 (4) N1—C24—C23—C22 11.1 (4) C9—C10—C11—C12 179.3 (3) N2—C1—C2—C3 −0.7 (5) C11—C12—N1—C24 −170.3 (2) N2—C5—C4—C3 −0.7 (4) C12—N1—C24—C23 90.9 (3) N3—C7—C8—C9 −0.4 (4) C13—N4—C17—C16 0.4 (4) N3—C11—C10—C9 0.2 (4) C13—N4—C17—C18 −178.7 (3) N4—C13—C14—C15 −1.4 (6) C13—C14—C15—C16 0.0 (6) N4—C17—C16—C15 −1.6 (5) C14—C13—N4—C17 1.2 (5) N4—C17—C18—N5 −13.3 (3) C14—C15—C16—C17 1.4 (5) N5—C18—C17—C16 167.6 (3) C15—C16—C17—C18 177.4 (3) N5—C19—C20—C21 0.4 (5) C17—C18—N5—C19 104.2 (3) N5—C23—C22—C21 −1.2 (4) C17—C18—N5—C23 −72.7 (3) C1—N2—C5—C4 1.6 (4) C18—N5—C19—C20 −176.0 (3) C1—N2—C5—C6 −176.3 (2) C18—N5—C23—C22 176.3 (2) C1—C2—C3—C4 1.5 (5) C18—N5—C23—C24 −2.0 (4) C2—C1—N2—C5 −0.9 (4) C19—N5—C23—C22 −0.6 (4) C2—C3—C4—C5 −0.8 (4) C19—N5—C23—C24 −178.9 (2) C3—C4—C5—C6 177.0 (3) C19—C20—C21—C22 −2.2 (5) C5—C6—N1—C12 −166.9 (2) C20—C19—N5—C23 0.9 (4) C5—C6—N1—C24 70.9 (3) C20—C21—C22—C23 2.6 (4) C6—N1—C12—C11 67.3 (3) C21—C22—C23—C24 177.0 (3) C6—N1—C24—C23 −146.2 (2)
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N2—H1···N3iii 0.95 1.79 2.706 (3) 162
