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

The title compound, C(15)H(25)N(5), is an aminalization product between 2,6-diacetyl-pyridine and 1,3-diamino-propane. It crystallizes with two independent mol-ecules in the asymmetric unit with different conformations. In the first mol-ecule, 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 mol-ecule [N-C-C-C torsion angles = 82.6 (1) and -90.8 (1)°]. Each of the two mol-ecules forms centrosymmetric dimers held together by N-H⋯N hydrogen bonds, thus forming R(2) (2)(16) rings. The two dimers are inter-linked by additional N-H⋯N bonds into R(4) (4)(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 = 275.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.35

5758 reflections

394 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050063/ng5081Isup2.hkl

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

C15H25N5	F(000) = 1200
Mr = 275.40	Dx = 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

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

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(Fo2) + (0.0513P)2] where P = (Fo2 + 2Fc2)/3
S = 1.35	(Δ/σ)max < 0.001
5758 reflections	Δρmax = 0.28 e Å−3
394 parameters	Δρmin = −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)

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
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)*

	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)

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)

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)

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) ; (ii) ; (iii) .