2,6-Bis(2-methyl-1,3-diazinan-2-yl)pyridine

Ton, Q.-C.; Bolte, M.

doi:10.1107/S1600536810050063

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o41

https://doi.org/10.1107/S1600536810050063

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2,6-Bis(2-methyl-1,3-diazinan-2-yl)pyridine

Quoc-Cuong Ton ^a and Michael Bolte ^b ^*

^aInstitut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and ^bInstitut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 29 November 2010; accepted 30 November 2010; online 8 December 2010)

The title compound, C₁₅H₂₅N₅, is an aminalization product between 2,6-diacetylpyridine and 1,3-diaminopropane. It crystallizes with two independent molecules in the asymmetric unit with different conformations. In the first molecule, the methyl groups are cis oriented with respect to the pyridine ring [N—C—C—C torsion angles = 72.5 (1) and 80.3 (1)°], while they are trans oriented in the second molecule [N—C—C—C torsion angles = 82.6 (1) and −90.8 (1)°]. Each of the two molecules forms centrosymmetric dimers held together by N—H⋯N hydrogen bonds, thus forming R₂²(16) rings. The two dimers are interlinked by additional N—H⋯N bonds into R₄⁴(14) rings, building chains along the a axis. These patterns influence the orientation (either equatorial or axial) of the N—H bonds.

Related literature

For 2,6-diacetylpyridine, see: Burnet et al. (2003 ) and for 1,3-diaminopropane, see: Thalladi et al. (2000 ).

Experimental

Crystal data

C₁₅H₂₅N₅
M_r = 275.40
Monoclinic, P 2₁ /c
a = 18.715 (4) Å
b = 7.512 (2) Å
c = 22.730 (5) Å
β = 102.07 (3)°
V = 3124.9 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 K
0.40 × 0.32 × 0.30 mm

Data collection

Stoe IPDS II two-circle diffractometer
41522 measured reflections
5758 independent reflections
4924 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.35
5758 reflections
394 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N5ⁱ	0.893 (16)	2.596 (15)	3.3984 (16)	149.9 (12)
N4—H4N⋯N4′ⁱⁱ	0.908 (16)	2.623 (16)	3.4716 (16)	155.8 (13)
N3′—H3′N⋯N5′ⁱⁱⁱ	0.873 (15)	2.418 (15)	3.2662 (17)	164.2 (12)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050063/ng5081sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050063/ng5081Isup2.hkl

checkCIF report

Comment top

The aim of this investigation was to cocrystallize 2,6-diacetylpyridine (Burnet et al., 2003) with 1,3-diaminopropane (Thalladi et al., 2000). Unfortunately crystals of the title compound were obtained due to an aminalization reaction between the starting compounds (Fig. 2).

Related literature top

For 2,6-diacetylpyridine, see: Burnet et al. (2003) and for 1,3-diaminopropane, see: Thalladi et al. (2000).

Experimental top

The starting compounds were purchased from Aldrich and Lancaster and utilized for a cocrystallization experiment without purification. 2,6-diacetylpyridine (10 mg) was added to an excess of 1,3-diaminopropane (0.8 ml). The mixture in a flask was set aside at room temperature. After several months colourless crystals were obtained.

Structure description top

For 2,6-diacetylpyridine, see: Burnet et al. (2003) and for 1,3-diaminopropane, see: Thalladi et al. (2000).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A partial packing diagram for (I). N—H···N hydrogen bonds are shown as dashed lines.
	Fig. 3. Reaction scheme between 2,6-diacetylpyridine and 1,3-diaminopropane.

2,6-Bis(2-methyl-1,3-diazinan-2-yl)pyridine top

Crystal data top

C₁₅H₂₅N₅	F(000) = 1200
M_r = 275.40	D_x = 1.171 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 38746 reflections
a = 18.715 (4) Å	θ = 3.3–25.7°
b = 7.512 (2) Å	µ = 0.07 mm⁻¹
c = 22.730 (5) Å	T = 173 K
β = 102.07 (3)°	Block, colourless
V = 3124.9 (13) Å³	0.40 × 0.32 × 0.30 mm
Z = 8

Data collection top

Stoe IPDS II two-circle diffractometer	4924 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 25.5°, θ_min = 3.3°
ω scans	h = −22→22
41522 measured reflections	k = −9→9
5758 independent reflections	l = −27→27

Refinement top

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0513P)²] where P = (F_o² + 2F_c²)/3
S = 1.35	(Δ/σ)_max < 0.001
5758 reflections	Δρ_max = 0.28 e Å⁻³
394 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0182 (13)

Crystal data top

C₁₅H₂₅N₅	V = 3124.9 (13) Å³
M_r = 275.40	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.715 (4) Å	µ = 0.07 mm⁻¹
b = 7.512 (2) Å	T = 173 K
c = 22.730 (5) Å	0.40 × 0.32 × 0.30 mm
β = 102.07 (3)°

Data collection top

Stoe IPDS II two-circle diffractometer	4924 reflections with I > 2σ(I)
41522 measured reflections	R_int = 0.050
5758 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.35	Δρ_max = 0.28 e Å⁻³
5758 reflections	Δρ_min = −0.18 e Å⁻³
394 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.01315 (5)	0.64048 (12)	0.38741 (4)	0.0208 (2)
C2	0.06102 (6)	0.70659 (15)	0.35629 (5)	0.0219 (2)
C3	0.03859 (7)	0.78073 (19)	0.29935 (6)	0.0337 (3)
H3	0.0733	0.8227	0.2775	0.040*
C4	−0.03613 (7)	0.7920 (2)	0.27508 (6)	0.0419 (4)
H4	−0.0530	0.8449	0.2367	0.050*
C5	−0.08588 (6)	0.72571 (18)	0.30721 (6)	0.0336 (3)
H5	−0.1370	0.7337	0.2915	0.040*
C6	−0.05903 (6)	0.64714 (15)	0.36306 (5)	0.0222 (2)
C7	0.14237 (5)	0.67781 (15)	0.38678 (5)	0.0205 (2)
C8	0.15860 (6)	0.47996 (15)	0.38048 (5)	0.0262 (3)
H8A	0.1275	0.4091	0.4013	0.039*
H8B	0.2101	0.4565	0.3984	0.039*
H8C	0.1486	0.4476	0.3378	0.039*
N2	0.15809 (5)	0.71862 (13)	0.45185 (4)	0.0226 (2)
H2N	0.1276 (8)	0.658 (2)	0.4698 (6)	0.034 (4)*
C9	0.15049 (7)	0.90860 (17)	0.46430 (6)	0.0319 (3)
H9A	0.1608	0.9292	0.5083	0.038*
H9B	0.0999	0.9482	0.4473	0.038*
C10	0.20407 (7)	1.01382 (17)	0.43596 (6)	0.0363 (3)
H10A	0.2548	0.9798	0.4548	0.044*
H10B	0.1982	1.1428	0.4426	0.044*
C11	0.18907 (7)	0.97400 (16)	0.36861 (6)	0.0325 (3)
H11A	0.1409	1.0243	0.3495	0.039*
H11B	0.2266	1.0338	0.3507	0.039*
N3	0.18942 (5)	0.78179 (13)	0.35523 (4)	0.0255 (2)
H3N	0.2350 (8)	0.7418 (18)	0.3682 (6)	0.028 (3)*
C12	−0.10820 (6)	0.56698 (15)	0.40310 (5)	0.0228 (2)
C13	−0.11675 (7)	0.70647 (19)	0.45014 (6)	0.0357 (3)
H13A	−0.0687	0.7351	0.4749	0.054*
H13B	−0.1483	0.6593	0.4758	0.054*
H13C	−0.1388	0.8144	0.4299	0.054*
N4	−0.18088 (5)	0.52752 (14)	0.36689 (5)	0.0267 (2)
H4N	−0.2100 (9)	0.506 (2)	0.3935 (7)	0.041 (4)*
C14	−0.18228 (7)	0.37221 (18)	0.32745 (6)	0.0339 (3)
H14A	−0.1575	0.4035	0.2944	0.041*
H14B	−0.2337	0.3429	0.3093	0.041*
C15	−0.14553 (7)	0.20842 (19)	0.35991 (7)	0.0405 (3)
H15A	−0.1422	0.1137	0.3303	0.049*
H15B	−0.1750	0.1627	0.3881	0.049*
C16	−0.06904 (7)	0.25698 (17)	0.39462 (7)	0.0353 (3)
H16A	−0.0463	0.1529	0.4180	0.042*
H16B	−0.0380	0.2916	0.3662	0.042*
N5	−0.07435 (5)	0.40640 (14)	0.43568 (4)	0.0270 (2)
H5N	−0.0281 (8)	0.4360 (19)	0.4533 (6)	0.033 (4)*
N1'	0.51250 (5)	0.59589 (12)	0.38384 (4)	0.0199 (2)
C2'	0.47119 (6)	0.66760 (14)	0.33387 (5)	0.0204 (2)
C3'	0.49877 (6)	0.70014 (16)	0.28223 (5)	0.0250 (3)
H3'	0.4691	0.7533	0.2477	0.030*
C4'	0.57073 (6)	0.65272 (16)	0.28268 (5)	0.0264 (3)
H4'	0.5907	0.6729	0.2481	0.032*
C5'	0.61335 (6)	0.57584 (16)	0.33375 (5)	0.0249 (2)
H5'	0.6624	0.5416	0.3346	0.030*
C6'	0.58237 (5)	0.55030 (14)	0.38369 (5)	0.0200 (2)
C7'	0.39231 (6)	0.71995 (15)	0.33837 (5)	0.0220 (2)
C8'	0.39689 (6)	0.90350 (16)	0.36847 (6)	0.0302 (3)
H8'1	0.4269	0.8954	0.4092	0.045*
H8'2	0.3477	0.9438	0.3705	0.045*
H8'3	0.4190	0.9886	0.3449	0.045*
N2'	0.34706 (5)	0.73352 (14)	0.27711 (4)	0.0272 (2)
H2'N	0.3052 (8)	0.7831 (19)	0.2808 (6)	0.033 (4)*
C9'	0.33042 (6)	0.55788 (17)	0.24825 (5)	0.0288 (3)
H9'1	0.3758	0.5078	0.2390	0.035*
H9'2	0.2950	0.5741	0.2097	0.035*
C10'	0.29904 (6)	0.42461 (17)	0.28693 (5)	0.0291 (3)
H10C	0.2955	0.3055	0.2679	0.035*
H10D	0.2494	0.4621	0.2904	0.035*
C11'	0.34896 (6)	0.41589 (15)	0.34943 (5)	0.0248 (2)
H11C	0.3271	0.3373	0.3759	0.030*
H11D	0.3971	0.3664	0.3465	0.030*
N3'	0.35806 (5)	0.59662 (13)	0.37478 (4)	0.0221 (2)
H3'N	0.3836 (8)	0.5952 (18)	0.4116 (7)	0.030 (3)*
C12'	0.62660 (6)	0.47668 (15)	0.44412 (5)	0.0208 (2)
C13'	0.66464 (7)	0.63378 (17)	0.48080 (6)	0.0335 (3)
H13D	0.6278	0.7182	0.4887	0.050*
H13E	0.6969	0.6935	0.4581	0.050*
H13F	0.6936	0.5902	0.5191	0.050*
N4'	0.68328 (5)	0.35340 (13)	0.43324 (5)	0.0256 (2)
H4'N	0.7143 (7)	0.3368 (18)	0.4685 (6)	0.029 (3)*
C14'	0.65331 (7)	0.18110 (18)	0.40894 (6)	0.0360 (3)
H14C	0.6943	0.0982	0.4084	0.043*
H14D	0.6268	0.1983	0.3668	0.043*
C15'	0.60164 (7)	0.09624 (18)	0.44454 (7)	0.0407 (3)
H15C	0.5785	−0.0105	0.4231	0.049*
H15D	0.6295	0.0584	0.4845	0.049*
C16'	0.54299 (7)	0.22950 (18)	0.45217 (6)	0.0364 (3)
H16C	0.5118	0.2578	0.4125	0.044*
H16D	0.5117	0.1777	0.4779	0.044*
N5'	0.57811 (5)	0.39283 (15)	0.48008 (4)	0.0281 (2)
H5'N	0.5420 (9)	0.474 (2)	0.4791 (7)	0.045 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0161 (4)	0.0239 (5)	0.0212 (5)	−0.0001 (3)	0.0011 (3)	−0.0006 (4)
C2	0.0188 (5)	0.0242 (6)	0.0218 (6)	−0.0005 (4)	0.0018 (4)	0.0006 (4)
C3	0.0234 (6)	0.0486 (8)	0.0277 (6)	−0.0040 (5)	0.0017 (5)	0.0137 (6)
C4	0.0289 (7)	0.0595 (9)	0.0320 (7)	−0.0031 (6)	−0.0056 (5)	0.0224 (6)
C5	0.0178 (6)	0.0443 (7)	0.0342 (7)	0.0009 (5)	−0.0045 (5)	0.0100 (6)
C6	0.0173 (5)	0.0243 (6)	0.0236 (6)	0.0012 (4)	0.0009 (4)	−0.0018 (4)
C7	0.0159 (5)	0.0249 (6)	0.0201 (5)	−0.0005 (4)	0.0023 (4)	0.0017 (4)
C8	0.0202 (5)	0.0270 (6)	0.0303 (6)	0.0006 (4)	0.0028 (5)	−0.0012 (5)
N2	0.0191 (5)	0.0267 (5)	0.0213 (5)	−0.0009 (4)	0.0023 (4)	0.0007 (4)
C9	0.0309 (6)	0.0304 (6)	0.0322 (6)	0.0033 (5)	0.0013 (5)	−0.0073 (5)
C10	0.0323 (7)	0.0230 (6)	0.0488 (8)	−0.0019 (5)	−0.0025 (6)	−0.0020 (5)
C11	0.0230 (6)	0.0291 (6)	0.0439 (7)	−0.0021 (5)	0.0036 (5)	0.0120 (6)
N3	0.0168 (5)	0.0310 (5)	0.0289 (5)	−0.0009 (4)	0.0052 (4)	0.0061 (4)
C12	0.0157 (5)	0.0292 (6)	0.0226 (5)	0.0007 (4)	0.0018 (4)	−0.0027 (5)
C13	0.0329 (7)	0.0418 (7)	0.0331 (7)	0.0005 (6)	0.0084 (5)	−0.0108 (6)
N4	0.0139 (4)	0.0379 (6)	0.0275 (5)	−0.0007 (4)	0.0030 (4)	−0.0043 (4)
C14	0.0268 (6)	0.0429 (8)	0.0298 (6)	−0.0083 (5)	0.0009 (5)	−0.0097 (5)
C15	0.0377 (7)	0.0336 (7)	0.0498 (8)	−0.0065 (6)	0.0080 (6)	−0.0106 (6)
C16	0.0289 (6)	0.0289 (7)	0.0483 (8)	0.0030 (5)	0.0089 (6)	0.0010 (6)
N5	0.0191 (5)	0.0340 (6)	0.0264 (5)	−0.0008 (4)	0.0012 (4)	0.0034 (4)
N1'	0.0170 (4)	0.0236 (5)	0.0187 (4)	0.0017 (3)	0.0028 (3)	0.0017 (4)
C2'	0.0189 (5)	0.0215 (5)	0.0202 (5)	0.0008 (4)	0.0023 (4)	0.0024 (4)
C3'	0.0245 (6)	0.0293 (6)	0.0207 (6)	0.0008 (5)	0.0036 (4)	0.0076 (5)
C4'	0.0267 (6)	0.0338 (6)	0.0208 (6)	−0.0018 (5)	0.0093 (4)	0.0047 (5)
C5'	0.0180 (5)	0.0328 (6)	0.0247 (6)	0.0012 (4)	0.0066 (4)	0.0021 (5)
C6'	0.0173 (5)	0.0216 (5)	0.0208 (5)	0.0003 (4)	0.0033 (4)	0.0003 (4)
C7'	0.0189 (5)	0.0275 (6)	0.0189 (5)	0.0041 (4)	0.0025 (4)	0.0033 (4)
C8'	0.0259 (6)	0.0290 (6)	0.0351 (7)	0.0041 (5)	0.0054 (5)	0.0001 (5)
N2'	0.0222 (5)	0.0360 (6)	0.0212 (5)	0.0102 (4)	−0.0005 (4)	0.0057 (4)
C9'	0.0226 (6)	0.0433 (7)	0.0183 (5)	0.0057 (5)	−0.0005 (4)	−0.0012 (5)
C10'	0.0198 (5)	0.0392 (7)	0.0276 (6)	−0.0005 (5)	0.0032 (5)	−0.0072 (5)
C11'	0.0210 (5)	0.0284 (6)	0.0254 (6)	0.0007 (4)	0.0057 (4)	0.0016 (5)
N3'	0.0188 (4)	0.0295 (5)	0.0173 (5)	0.0020 (4)	0.0023 (4)	0.0013 (4)
C12'	0.0168 (5)	0.0264 (6)	0.0192 (5)	0.0033 (4)	0.0035 (4)	0.0016 (4)
C13'	0.0319 (6)	0.0324 (7)	0.0306 (6)	0.0023 (5)	−0.0060 (5)	−0.0019 (5)
N4'	0.0179 (5)	0.0331 (5)	0.0249 (5)	0.0073 (4)	0.0026 (4)	0.0025 (4)
C14'	0.0372 (7)	0.0330 (7)	0.0345 (7)	0.0135 (5)	0.0000 (6)	−0.0044 (5)
C15'	0.0383 (7)	0.0274 (7)	0.0484 (8)	−0.0012 (5)	−0.0094 (6)	0.0076 (6)
C16'	0.0224 (6)	0.0410 (7)	0.0421 (8)	−0.0046 (5)	−0.0018 (5)	0.0194 (6)
N5'	0.0213 (5)	0.0400 (6)	0.0242 (5)	0.0072 (4)	0.0074 (4)	0.0091 (4)

Geometric parameters (Å, º) top

N1—C2	1.3471 (15)	N1'—C2'	1.3456 (14)
N1—C6	1.3494 (14)	N1'—C6'	1.3523 (14)
C2—C3	1.3908 (17)	C2'—C3'	1.3992 (16)
C2—C7	1.5504 (15)	C2'—C7'	1.5515 (15)
C3—C4	1.3943 (18)	C3'—C4'	1.3909 (16)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.3903 (19)	C4'—C5'	1.3892 (17)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.3949 (17)	C5'—C6'	1.3916 (16)
C5—H5	0.9500	C5'—H5'	0.9500
C6—C12	1.5453 (16)	C6'—C12'	1.5499 (15)
C7—N3	1.4709 (14)	C7'—N2'	1.4742 (15)
C7—N2	1.4786 (15)	C7'—N3'	1.4752 (15)
C7—C8	1.5297 (16)	C7'—C8'	1.5337 (17)
C8—H8A	0.9800	C8'—H8'1	0.9800
C8—H8B	0.9800	C8'—H8'2	0.9800
C8—H8C	0.9800	C8'—H8'3	0.9800
N2—C9	1.4676 (16)	N2'—C9'	1.4774 (17)
N2—H2N	0.893 (16)	N2'—H2'N	0.887 (15)
C9—C10	1.5217 (19)	C9'—C10'	1.5284 (18)
C9—H9A	0.9900	C9'—H9'1	0.9900
C9—H9B	0.9900	C9'—H9'2	0.9900
C10—C11	1.527 (2)	C10'—C11'	1.5297 (17)
C10—H10A	0.9900	C10'—H10C	0.9900
C10—H10B	0.9900	C10'—H10D	0.9900
C11—N3	1.4758 (17)	C11'—N3'	1.4707 (15)
C11—H11A	0.9900	C11'—H11C	0.9900
C11—H11B	0.9900	C11'—H11D	0.9900
N3—H3N	0.894 (14)	N3'—H3'N	0.873 (15)
C12—N4	1.4653 (14)	C12'—N4'	1.4676 (14)
C12—N5	1.4862 (15)	C12'—N5'	1.4830 (15)
C12—C13	1.5293 (17)	C12'—C13'	1.5318 (16)
C13—H13A	0.9800	C13'—H13D	0.9800
C13—H13B	0.9800	C13'—H13E	0.9800
C13—H13C	0.9800	C13'—H13F	0.9800
N4—C14	1.4683 (16)	N4'—C14'	1.4715 (17)
N4—H4N	0.908 (16)	N4'—H4'N	0.894 (14)
C14—C15	1.523 (2)	C14'—C15'	1.524 (2)
C14—H14A	0.9900	C14'—H14C	0.9900
C14—H14B	0.9900	C14'—H14D	0.9900
C15—C16	1.5271 (19)	C15'—C16'	1.522 (2)
C15—H15A	0.9900	C15'—H15C	0.9900
C15—H15B	0.9900	C15'—H15D	0.9900
C16—N5	1.4764 (17)	C16'—N5'	1.4715 (18)
C16—H16A	0.9900	C16'—H16C	0.9900
C16—H16B	0.9900	C16'—H16D	0.9900
N5—H5N	0.901 (15)	N5'—H5'N	0.905 (17)

C2—N1—C6	119.31 (9)	C2'—N1'—C6'	118.98 (9)
N1—C2—C3	122.14 (10)	N1'—C2'—C3'	122.03 (10)
N1—C2—C7	114.37 (9)	N1'—C2'—C7'	115.63 (9)
C3—C2—C7	123.29 (10)	C3'—C2'—C7'	122.28 (10)
C2—C3—C4	118.36 (12)	C4'—C3'—C2'	118.40 (10)
C2—C3—H3	120.8	C4'—C3'—H3'	120.8
C4—C3—H3	120.8	C2'—C3'—H3'	120.8
C5—C4—C3	119.79 (11)	C5'—C4'—C3'	119.90 (11)
C5—C4—H4	120.1	C5'—C4'—H4'	120.1
C3—C4—H4	120.1	C3'—C4'—H4'	120.1
C4—C5—C6	118.44 (11)	C4'—C5'—C6'	118.32 (10)
C4—C5—H5	120.8	C4'—C5'—H5'	120.8
C6—C5—H5	120.8	C6'—C5'—H5'	120.8
N1—C6—C5	121.89 (11)	N1'—C6'—C5'	122.36 (10)
N1—C6—C12	114.35 (9)	N1'—C6'—C12'	115.19 (9)
C5—C6—C12	123.73 (10)	C5'—C6'—C12'	122.38 (9)
N3—C7—N2	111.31 (9)	N2'—C7'—N3'	110.01 (9)
N3—C7—C8	108.63 (9)	N2'—C7'—C8'	109.07 (9)
N2—C7—C8	107.05 (9)	N3'—C7'—C8'	107.73 (9)
N3—C7—C2	109.88 (9)	N2'—C7'—C2'	108.77 (9)
N2—C7—C2	112.93 (9)	N3'—C7'—C2'	114.13 (9)
C8—C7—C2	106.82 (9)	C8'—C7'—C2'	106.99 (9)
C7—C8—H8A	109.5	C7'—C8'—H8'1	109.5
C7—C8—H8B	109.5	C7'—C8'—H8'2	109.5
H8A—C8—H8B	109.5	H8'1—C8'—H8'2	109.5
C7—C8—H8C	109.5	C7'—C8'—H8'3	109.5
H8A—C8—H8C	109.5	H8'1—C8'—H8'3	109.5
H8B—C8—H8C	109.5	H8'2—C8'—H8'3	109.5
C9—N2—C7	112.79 (9)	C7'—N2'—C9'	112.56 (9)
C9—N2—H2N	108.2 (9)	C7'—N2'—H2'N	106.5 (9)
C7—N2—H2N	109.7 (9)	C9'—N2'—H2'N	108.0 (9)
N2—C9—C10	108.94 (10)	N2'—C9'—C10'	113.59 (10)
N2—C9—H9A	109.9	N2'—C9'—H9'1	108.8
C10—C9—H9A	109.9	C10'—C9'—H9'1	108.8
N2—C9—H9B	109.9	N2'—C9'—H9'2	108.8
C10—C9—H9B	109.9	C10'—C9'—H9'2	108.8
H9A—C9—H9B	108.3	H9'1—C9'—H9'2	107.7
C9—C10—C11	108.86 (10)	C9'—C10'—C11'	109.20 (9)
C9—C10—H10A	109.9	C9'—C10'—H10C	109.8
C11—C10—H10A	109.9	C11'—C10'—H10C	109.8
C9—C10—H10B	109.9	C9'—C10'—H10D	109.8
C11—C10—H10B	109.9	C11'—C10'—H10D	109.8
H10A—C10—H10B	108.3	H10C—C10'—H10D	108.3
N3—C11—C10	112.98 (10)	N3'—C11'—C10'	108.81 (9)
N3—C11—H11A	109.0	N3'—C11'—H11C	109.9
C10—C11—H11A	109.0	C10'—C11'—H11C	109.9
N3—C11—H11B	109.0	N3'—C11'—H11D	109.9
C10—C11—H11B	109.0	C10'—C11'—H11D	109.9
H11A—C11—H11B	107.8	H11C—C11'—H11D	108.3
C7—N3—C11	112.97 (10)	C11'—N3'—C7'	112.85 (9)
C7—N3—H3N	106.7 (9)	C11'—N3'—H3'N	111.1 (9)
C11—N3—H3N	107.8 (9)	C7'—N3'—H3'N	109.3 (9)
N4—C12—N5	111.38 (9)	N4'—C12'—N5'	111.85 (9)
N4—C12—C13	108.09 (9)	N4'—C12'—C13'	107.93 (9)
N5—C12—C13	107.68 (10)	N5'—C12'—C13'	107.19 (9)
N4—C12—C6	110.20 (9)	N4'—C12'—C6'	110.29 (9)
N5—C12—C6	111.44 (9)	N5'—C12'—C6'	111.41 (8)
C13—C12—C6	107.89 (10)	C13'—C12'—C6'	107.99 (9)
C12—C13—H13A	109.5	C12'—C13'—H13D	109.5
C12—C13—H13B	109.5	C12'—C13'—H13E	109.5
H13A—C13—H13B	109.5	H13D—C13'—H13E	109.5
C12—C13—H13C	109.5	C12'—C13'—H13F	109.5
H13A—C13—H13C	109.5	H13D—C13'—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13'—H13F	109.5
C12—N4—C14	113.55 (9)	C12'—N4'—C14'	112.71 (9)
C12—N4—H4N	106.1 (10)	C12'—N4'—H4'N	107.1 (9)
C14—N4—H4N	109.3 (10)	C14'—N4'—H4'N	109.8 (9)
N4—C14—C15	113.43 (11)	N4'—C14'—C15'	113.76 (11)
N4—C14—H14A	108.9	N4'—C14'—H14C	108.8
C15—C14—H14A	108.9	C15'—C14'—H14C	108.8
N4—C14—H14B	108.9	N4'—C14'—H14D	108.8
C15—C14—H14B	108.9	C15'—C14'—H14D	108.8
H14A—C14—H14B	107.7	H14C—C14'—H14D	107.7
C14—C15—C16	109.68 (11)	C16'—C15'—C14'	109.76 (11)
C14—C15—H15A	109.7	C16'—C15'—H15C	109.7
C16—C15—H15A	109.7	C14'—C15'—H15C	109.7
C14—C15—H15B	109.7	C16'—C15'—H15D	109.7
C16—C15—H15B	109.7	C14'—C15'—H15D	109.7
H15A—C15—H15B	108.2	H15C—C15'—H15D	108.2
N5—C16—C15	109.18 (10)	N5'—C16'—C15'	109.26 (10)
N5—C16—H16A	109.8	N5'—C16'—H16C	109.8
C15—C16—H16A	109.8	C15'—C16'—H16C	109.8
N5—C16—H16B	109.8	N5'—C16'—H16D	109.8
C15—C16—H16B	109.8	C15'—C16'—H16D	109.8
H16A—C16—H16B	108.3	H16C—C16'—H16D	108.3
C16—N5—C12	112.33 (9)	C16'—N5'—C12'	112.71 (10)
C16—N5—H5N	106.5 (9)	C16'—N5'—H5'N	106.6 (10)
C12—N5—H5N	106.9 (9)	C12'—N5'—H5'N	103.9 (10)

C6—N1—C2—C3	−0.52 (17)	C6'—N1'—C2'—C3'	−1.46 (16)
C6—N1—C2—C7	−175.43 (9)	C6'—N1'—C2'—C7'	−178.67 (9)
N1—C2—C3—C4	2.3 (2)	N1'—C2'—C3'—C4'	1.42 (17)
C7—C2—C3—C4	176.79 (12)	C7'—C2'—C3'—C4'	178.44 (10)
C2—C3—C4—C5	−1.6 (2)	C2'—C3'—C4'—C5'	−0.30 (18)
C3—C4—C5—C6	−0.8 (2)	C3'—C4'—C5'—C6'	−0.70 (18)
C2—N1—C6—C5	−2.05 (17)	C2'—N1'—C6'—C5'	0.39 (16)
C2—N1—C6—C12	179.94 (9)	C2'—N1'—C6'—C12'	177.37 (9)
C4—C5—C6—N1	2.68 (19)	C4'—C5'—C6'—N1'	0.68 (17)
C4—C5—C6—C12	−179.50 (12)	C4'—C5'—C6'—C12'	−176.09 (10)
N1—C2—C7—N3	−169.79 (9)	N1'—C2'—C7'—N2'	−159.75 (9)
C3—C2—C7—N3	15.36 (15)	C3'—C2'—C7'—N2'	23.05 (14)
N1—C2—C7—N2	−44.86 (13)	N1'—C2'—C7'—N3'	−36.50 (13)
C3—C2—C7—N2	140.29 (12)	C3'—C2'—C7'—N3'	146.30 (11)
N1—C2—C7—C8	72.55 (12)	N1'—C2'—C7'—C8'	82.56 (12)
C3—C2—C7—C8	−102.30 (13)	C3'—C2'—C7'—C8'	−94.63 (12)
N3—C7—N2—C9	56.72 (12)	N3'—C7'—N2'—C9'	−53.26 (12)
C8—C7—N2—C9	175.30 (9)	C8'—C7'—N2'—C9'	−171.21 (10)
C2—C7—N2—C9	−67.42 (12)	C2'—C7'—N2'—C9'	72.43 (12)
C7—N2—C9—C10	−60.40 (12)	C7'—N2'—C9'—C10'	51.37 (13)
N2—C9—C10—C11	57.28 (13)	N2'—C9'—C10'—C11'	−51.67 (13)
C9—C10—C11—N3	−53.72 (13)	C9'—C10'—C11'—N3'	55.04 (12)
N2—C7—N3—C11	−50.79 (12)	C10'—C11'—N3'—C7'	−61.18 (11)
C8—C7—N3—C11	−168.41 (9)	N2'—C7'—N3'—C11'	59.80 (11)
C2—C7—N3—C11	75.06 (11)	C8'—C7'—N3'—C11'	178.57 (9)
C10—C11—N3—C7	50.98 (13)	C2'—C7'—N3'—C11'	−62.78 (12)
N1—C6—C12—N4	−161.87 (9)	N1'—C6'—C12'—N4'	151.51 (9)
C5—C6—C12—N4	20.16 (16)	C5'—C6'—C12'—N4'	−31.51 (15)
N1—C6—C12—N5	−37.69 (13)	N1'—C6'—C12'—N5'	26.68 (13)
C5—C6—C12—N5	144.34 (12)	C5'—C6'—C12'—N5'	−156.34 (10)
N1—C6—C12—C13	80.32 (12)	N1'—C6'—C12'—C13'	−90.77 (11)
C5—C6—C12—C13	−97.65 (13)	C5'—C6'—C12'—C13'	86.21 (13)
N5—C12—N4—C14	−51.19 (13)	N5'—C12'—N4'—C14'	50.94 (13)
C13—C12—N4—C14	−169.29 (11)	C13'—C12'—N4'—C14'	168.61 (10)
C6—C12—N4—C14	73.03 (13)	C6'—C12'—N4'—C14'	−73.64 (12)
C12—N4—C14—C15	50.09 (15)	C12'—N4'—C14'—C15'	−50.04 (13)
N4—C14—C15—C16	−51.80 (15)	N4'—C14'—C15'—C16'	52.01 (14)
C14—C15—C16—N5	55.64 (15)	C14'—C15'—C16'—N5'	−55.21 (14)
C15—C16—N5—C12	−59.44 (14)	C15'—C16'—N5'—C12'	58.90 (13)
N4—C12—N5—C16	56.92 (12)	N4'—C12'—N5'—C16'	−56.78 (12)
C13—C12—N5—C16	175.27 (9)	C13'—C12'—N5'—C16'	−174.89 (9)
C6—C12—N5—C16	−66.59 (12)	C6'—C12'—N5'—C16'	67.17 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N5ⁱ	0.893 (16)	2.596 (15)	3.3984 (16)	149.9 (12)
N4—H4N···N4′ⁱⁱ	0.908 (16)	2.623 (16)	3.4716 (16)	155.8 (13)
N3′—H3′N···N5′ⁱⁱⁱ	0.873 (15)	2.418 (15)	3.2662 (17)	164.2 (12)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₅N₅
M_r	275.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	18.715 (4), 7.512 (2), 22.730 (5)
β (°)	102.07 (3)
V (Å³)	3124.9 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.32 × 0.30

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	41522, 5758, 4924
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.35
No. of reflections	5758
No. of parameters	394
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.18

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N5ⁱ	0.893 (16)	2.596 (15)	3.3984 (16)	149.9 (12)
N4—H4N···N4'ⁱⁱ	0.908 (16)	2.623 (16)	3.4716 (16)	155.8 (13)
N3'—H3'N···N5'ⁱⁱⁱ	0.873 (15)	2.418 (15)	3.2662 (17)	164.2 (12)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1.

Acknowledgements

We gratefully thank Professor Dr Ernst Egert for his support.

References

Burnet, S., Hall, A. K., Hall, J. M., Harrowfield, J. M., Koutsantonis, G. A., Sanford, V., Sauter, D., Skelton, B. W. & White, A. H. (2003). Supramol. Chem. 15, 291–312. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Thalladi, V. R., Boese, R. & Weiss, C.-H. (2000). Angew. Chem. Int. Ed. 39, 918–922. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar