5,5-Dimethyl-2,2-bis-(pyridin-2-yl)-1,3-diazinane.

In the mol-ecule of the title compound, C(16)H(20)N(4), the 1,3-diazinane ring adopts a chair conformation and the dihedral angle formed by the pyridine rings is 78.64 (8)°. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, centrosymmetrically related mol-ecules are linked into dimers by pairs of N-H⋯N hydrogen bonds, generating rings of R(2) (2)(10) graph-set motif.

Related literature

For the structures of related hexa­hydro­pyrimidines, see: Al-Resayes (2009 ▶); Song et al. (2010 ▶); Jayaratna & Norman (2010 ▶); Fun & Kia (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H20N4

M = 268.36

Triclinic,

a = 8.5535 (7) Å

b = 8.7124 (8) Å

c = 11.7241 (10) Å

α = 109.824 (2)°

β = 96.444 (2)°

γ = 109.658 (2)°

V = 748.33 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.48 × 0.42 × 0.39 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.966, T max = 0.972

8514 measured reflections

2794 independent reflections

2422 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.05

2794 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021629/rz2740sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021629/rz2740Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021629/rz2740Isup3.cml

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

C16H20N4	Z = 2
Mr = 268.36	F(000) = 288
Triclinic, P1	Dx = 1.191 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5535 (7) Å	Cell parameters from 3809 reflections
b = 8.7124 (8) Å	θ = 2.6–28.3°
c = 11.7241 (10) Å	µ = 0.07 mm−1
α = 109.824 (2)°	T = 298 K
β = 96.444 (2)°	Block, colourless
γ = 109.658 (2)°	0.48 × 0.42 × 0.39 mm
V = 748.33 (11) Å3

Bruker SMART APEX CCD area-detector diffractometer	2794 independent reflections
Radiation source: fine-focus sealed tube	2422 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scan	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.966, Tmax = 0.972	k = −10→10
8514 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1284P] where P = (Fo2 + 2Fc2)/3
2794 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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	0.77584 (15)	0.69943 (16)	0.23880 (11)	0.0588 (3)
N2	0.52797 (14)	0.27820 (13)	0.38100 (9)	0.0441 (3)
N3	0.48652 (13)	0.40322 (14)	0.11970 (9)	0.0414 (3)
N4	0.45050 (13)	0.53799 (13)	0.32684 (9)	0.0408 (3)
C1	0.9335 (2)	0.8284 (2)	0.28056 (17)	0.0732 (5)
H1B	0.9634	0.9024	0.2381	0.088*
C2	1.0538 (2)	0.8587 (2)	0.38177 (17)	0.0741 (5)
H2B	1.1621	0.9506	0.4075	0.089*
C3	1.0101 (2)	0.7500 (2)	0.44384 (18)	0.0772 (5)
H3B	1.0884	0.7667	0.5133	0.093*
C4	0.84908 (19)	0.6155 (2)	0.40254 (14)	0.0635 (4)
H4B	0.8173	0.5398	0.4436	0.076*
C5	0.73434 (16)	0.59355 (16)	0.29919 (11)	0.0418 (3)
C6	0.54948 (15)	0.45228 (15)	0.25295 (10)	0.0371 (3)
C7	0.54779 (14)	0.28446 (15)	0.27106 (10)	0.0371 (3)
C8	0.57432 (17)	0.15174 (17)	0.17968 (12)	0.0464 (3)
H8A	0.5886	0.1597	0.1041	0.056*
C9	0.57920 (19)	0.00820 (18)	0.20247 (13)	0.0557 (4)
H9A	0.5958	−0.0825	0.1421	0.067*
C10	0.55928 (18)	0.00035 (17)	0.31533 (13)	0.0529 (3)
H10A	0.5625	−0.0949	0.3332	0.063*
C11	0.53455 (18)	0.13749 (17)	0.40084 (12)	0.0495 (3)
H11A	0.5215	0.1325	0.4774	0.059*
C12	0.30105 (16)	0.30123 (17)	0.07347 (11)	0.0452 (3)
H12A	0.2747	0.1844	0.0745	0.054*
H12B	0.2666	0.2844	−0.0131	0.054*
C13	0.19391 (16)	0.38596 (18)	0.14765 (12)	0.0482 (3)
C14	0.26589 (16)	0.42847 (18)	0.28538 (12)	0.0481 (3)
H14A	0.2074	0.4911	0.3369	0.058*
H14B	0.2444	0.3183	0.2962	0.058*
C15	0.0071 (2)	0.2539 (2)	0.10458 (17)	0.0744 (5)
H15A	0.0000	0.1476	0.1154	0.112*
H15B	−0.0376	0.2248	0.0176	0.112*
H15C	−0.0588	0.3060	0.1535	0.112*
C16	0.2069 (2)	0.5537 (2)	0.12841 (15)	0.0634 (4)
H16A	0.1669	0.5240	0.0407	0.095*
H16B	0.3243	0.6381	0.1585	0.095*
H16C	0.1376	0.6048	0.1739	0.095*
H4A	0.4891 (17)	0.5588 (17)	0.4059 (14)	0.049 (4)*
H3A	0.5166 (18)	0.502 (2)	0.1080 (13)	0.051 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0570 (7)	0.0547 (7)	0.0576 (7)	0.0107 (6)	0.0113 (6)	0.0271 (6)
N2	0.0578 (6)	0.0430 (6)	0.0357 (5)	0.0239 (5)	0.0133 (5)	0.0164 (4)
N3	0.0465 (6)	0.0455 (6)	0.0314 (5)	0.0176 (5)	0.0093 (4)	0.0156 (4)
N4	0.0509 (6)	0.0441 (6)	0.0308 (5)	0.0250 (5)	0.0112 (4)	0.0130 (4)
C1	0.0675 (10)	0.0612 (9)	0.0758 (11)	0.0059 (8)	0.0196 (9)	0.0294 (8)
C2	0.0477 (8)	0.0607 (10)	0.0834 (12)	0.0063 (7)	0.0121 (8)	0.0102 (9)
C3	0.0560 (10)	0.0700 (10)	0.0780 (11)	0.0142 (8)	−0.0112 (8)	0.0177 (9)
C4	0.0582 (9)	0.0594 (9)	0.0599 (9)	0.0138 (7)	−0.0033 (7)	0.0246 (7)
C5	0.0463 (7)	0.0389 (6)	0.0384 (6)	0.0190 (5)	0.0105 (5)	0.0115 (5)
C6	0.0440 (6)	0.0386 (6)	0.0294 (6)	0.0187 (5)	0.0099 (5)	0.0120 (5)
C7	0.0383 (6)	0.0380 (6)	0.0328 (6)	0.0158 (5)	0.0078 (5)	0.0116 (5)
C8	0.0555 (8)	0.0464 (7)	0.0395 (6)	0.0249 (6)	0.0171 (6)	0.0140 (5)
C9	0.0697 (9)	0.0459 (7)	0.0539 (8)	0.0322 (7)	0.0197 (7)	0.0126 (6)
C10	0.0636 (9)	0.0413 (7)	0.0568 (8)	0.0246 (6)	0.0116 (6)	0.0208 (6)
C11	0.0623 (8)	0.0482 (7)	0.0434 (7)	0.0245 (6)	0.0138 (6)	0.0223 (6)
C12	0.0490 (7)	0.0460 (7)	0.0341 (6)	0.0176 (6)	0.0044 (5)	0.0123 (5)
C13	0.0436 (7)	0.0511 (7)	0.0481 (7)	0.0204 (6)	0.0081 (6)	0.0175 (6)
C14	0.0508 (7)	0.0547 (8)	0.0476 (7)	0.0277 (6)	0.0208 (6)	0.0216 (6)
C15	0.0485 (9)	0.0805 (11)	0.0793 (11)	0.0187 (8)	0.0106 (8)	0.0238 (9)
C16	0.0696 (10)	0.0649 (9)	0.0607 (9)	0.0374 (8)	0.0055 (7)	0.0241 (7)

N1—C5	1.3256 (17)	C8—C9	1.3771 (18)
N1—C1	1.3339 (19)	C8—H8A	0.9300
N2—C7	1.3354 (15)	C9—C10	1.374 (2)
N2—C11	1.3406 (16)	C9—H9A	0.9300
N3—C6	1.4549 (14)	C10—C11	1.3721 (19)
N3—C12	1.4601 (16)	C10—H10A	0.9300
N3—H3A	0.878 (15)	C11—H11A	0.9300
N4—C14	1.4627 (16)	C12—C13	1.5296 (18)
N4—C6	1.4751 (14)	C12—H12A	0.9700
N4—H4A	0.883 (15)	C12—H12B	0.9700
C1—C2	1.367 (3)	C13—C15	1.5230 (19)
C1—H1B	0.9300	C13—C16	1.5231 (19)
C2—C3	1.362 (3)	C13—C14	1.5301 (18)
C2—H2B	0.9300	C14—H14A	0.9700
C3—C4	1.373 (2)	C14—H14B	0.9700
C3—H3B	0.9300	C15—H15A	0.9600
C4—C5	1.3847 (19)	C15—H15B	0.9600
C4—H4B	0.9300	C15—H15C	0.9600
C5—C6	1.5345 (16)	C16—H16A	0.9600
C6—C7	1.5428 (16)	C16—H16B	0.9600
C7—C8	1.3883 (16)	C16—H16C	0.9600
C5—N1—C1	117.63 (13)	C8—C9—H9A	120.3
C7—N2—C11	117.43 (11)	C11—C10—C9	117.89 (12)
C6—N3—C12	113.05 (9)	C11—C10—H10A	121.1
C6—N3—H3A	107.0 (9)	C9—C10—H10A	121.1
C12—N3—H3A	110.8 (9)	N2—C11—C10	124.11 (12)
C14—N4—C6	112.88 (9)	N2—C11—H11A	117.9
C14—N4—H4A	109.5 (9)	C10—C11—H11A	117.9
C6—N4—H4A	107.7 (9)	N3—C12—C13	114.99 (10)
N1—C1—C2	124.19 (16)	N3—C12—H12A	108.5
N1—C1—H1B	117.9	C13—C12—H12A	108.5
C2—C1—H1B	117.9	N3—C12—H12B	108.5
C3—C2—C1	117.92 (15)	C13—C12—H12B	108.5
C3—C2—H2B	121.0	H12A—C12—H12B	107.5
C1—C2—H2B	121.0	C15—C13—C16	109.87 (12)
C2—C3—C4	119.16 (16)	C15—C13—C12	109.76 (11)
C2—C3—H3B	120.4	C16—C13—C12	109.97 (11)
C4—C3—H3B	120.4	C15—C13—C14	109.29 (12)
C3—C4—C5	119.43 (15)	C16—C13—C14	111.33 (11)
C3—C4—H4B	120.3	C12—C13—C14	106.57 (10)
C5—C4—H4B	120.3	N4—C14—C13	111.30 (10)
N1—C5—C4	121.67 (13)	N4—C14—H14A	109.4
N1—C5—C6	116.42 (11)	C13—C14—H14A	109.4
C4—C5—C6	121.82 (12)	N4—C14—H14B	109.4
N3—C6—N4	111.25 (9)	C13—C14—H14B	109.4
N3—C6—C5	109.18 (9)	H14A—C14—H14B	108.0
N4—C6—C5	105.31 (9)	C13—C15—H15A	109.5
N3—C6—C7	108.16 (9)	C13—C15—H15B	109.5
N4—C6—C7	113.60 (9)	H15A—C15—H15B	109.5
C5—C6—C7	109.24 (9)	C13—C15—H15C	109.5
N2—C7—C8	122.12 (11)	H15A—C15—H15C	109.5
N2—C7—C6	116.56 (10)	H15B—C15—H15C	109.5
C8—C7—C6	121.24 (10)	C13—C16—H16A	109.5
C9—C8—C7	119.09 (12)	C13—C16—H16B	109.5
C9—C8—H8A	120.5	H16A—C16—H16B	109.5
C7—C8—H8A	120.5	C13—C16—H16C	109.5
C10—C9—C8	119.35 (12)	H16A—C16—H16C	109.5
C10—C9—H9A	120.3	H16B—C16—H16C	109.5
C5—N1—C1—C2	−0.5 (3)	C11—N2—C7—C6	−176.83 (10)
N1—C1—C2—C3	0.1 (3)	N3—C6—C7—N2	−151.87 (10)
C1—C2—C3—C4	0.2 (3)	N4—C6—C7—N2	−27.85 (14)
C2—C3—C4—C5	−0.3 (3)	C5—C6—C7—N2	89.39 (12)
C1—N1—C5—C4	0.4 (2)	N3—C6—C7—C8	31.27 (15)
C1—N1—C5—C6	177.15 (12)	N4—C6—C7—C8	155.30 (11)
C3—C4—C5—N1	−0.1 (2)	C5—C6—C7—C8	−87.47 (13)
C3—C4—C5—C6	−176.63 (13)	N2—C7—C8—C9	0.47 (19)
C12—N3—C6—N4	−51.01 (13)	C6—C7—C8—C9	177.15 (11)
C12—N3—C6—C5	−166.81 (9)	C7—C8—C9—C10	−0.6 (2)
C12—N3—C6—C7	74.41 (12)	C8—C9—C10—C11	0.2 (2)
C14—N4—C6—N3	55.48 (13)	C7—N2—C11—C10	−0.4 (2)
C14—N4—C6—C5	173.65 (9)	C9—C10—C11—N2	0.3 (2)
C14—N4—C6—C7	−66.85 (12)	C6—N3—C12—C13	52.20 (14)
N1—C5—C6—N3	29.03 (14)	N3—C12—C13—C15	−170.46 (11)
C4—C5—C6—N3	−154.24 (12)	N3—C12—C13—C16	68.56 (14)
N1—C5—C6—N4	−90.52 (12)	N3—C12—C13—C14	−52.23 (14)
C4—C5—C6—N4	86.21 (14)	C6—N4—C14—C13	−58.94 (13)
N1—C5—C6—C7	147.13 (11)	C15—C13—C14—N4	173.16 (11)
C4—C5—C6—C7	−36.15 (15)	C16—C13—C14—N4	−65.29 (14)
C11—N2—C7—C8	0.00 (18)	C12—C13—C14—N4	54.62 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N2i	0.882 (15)	2.469 (15)	3.2048 (14)	141.3 (13)
C4—H4B···N2	0.93	2.55	3.187 (2)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N2i	0.882 (15)	2.469 (15)	3.2048 (14)	141.3 (13)
C4—H4B⋯N2	0.93	2.55	3.187 (2)	126

Symmetry code: (i) .