2-Methyl-2-(2-pyrid-yl)hexa-hydro-pyrimidine.

In the aminal-type title compound, C(10)H(15)N(3), the six-membered hexa-hydro-pyrimidine ring adopts a chair conformation and the N atoms are pyramidally coordinated. One of the two amido -NH units engages in inter-molecular hydrogen bonding with the pyridyl N atom, generating a helical chain running along the b axis of the ortho-rhom-bic unit cell.

Related literature

The title compound is used in Fe(II) spin-crossover materials; see: Bréfuel et al. (2007 ▶).

Experimental

Crystal data

C10H15N3

M = 177.25

Orthorhombic,

a = 8.4070 (17) Å

b = 10.371 (2) Å

c = 11.363 (2) Å

V = 990.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 294 K

0.35 × 0.15 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007 ▶) T min = 0.97, T max = 0.99

8017 measured reflections

1324 independent reflections

1206 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.115

S = 1.01

1324 reflections

128 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶) and PLUTO (Motherwell et al., 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025963/ng2608sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025963/ng2608Isup2.hkl

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

C10H15N3	F(000) = 384
Mr = 177.25	Dx = 1.188 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7168 reflections
a = 8.4070 (17) Å	θ = 3.0–27.5°
b = 10.371 (2) Å	µ = 0.07 mm−1
c = 11.363 (2) Å	T = 294 K
V = 990.7 (3) Å3	Plate, yellow
Z = 4	0.35 × 0.15 × 0.15 mm

Rigaku R-AXIS RAPID diffractometer	1324 independent reflections
Radiation source: fine-focus sealed tube	1206 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007)	h = −10→10
Tmin = 0.97, Tmax = 0.99	k = −13→12
8017 measured reflections	l = −13→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0907P)2 + 0.0352P] where P = (Fo2 + 2Fc2)/3
1324 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.34 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	0.20810 (17)	0.34068 (14)	0.21846 (15)	0.0473 (4)
C1	0.3442 (2)	0.27459 (18)	0.2066 (2)	0.0562 (5)
H1	0.3416	0.1859	0.2183	0.067*
N2	0.05820 (18)	0.66511 (13)	0.16234 (14)	0.0475 (3)
H2A	−0.026 (3)	0.711 (2)	0.187 (2)	0.063 (6)*
C2	0.4872 (2)	0.3304 (2)	0.17791 (18)	0.0553 (5)
H2	0.5789	0.2809	0.1707	0.066*
N3	−0.08570 (15)	0.46514 (15)	0.18351 (14)	0.0436 (3)
H3A	−0.087 (3)	0.391 (2)	0.221 (2)	0.063 (6)*
C3	0.49114 (19)	0.4615 (2)	0.16021 (17)	0.0518 (4)
H3	0.5861	0.5025	0.1410	0.062*
C4	0.35197 (19)	0.53176 (17)	0.17129 (16)	0.0445 (4)
H4	0.3523	0.6205	0.1599	0.053*
C5	0.21182 (17)	0.46810 (14)	0.19969 (13)	0.0364 (3)
C6	0.05402 (18)	0.53948 (14)	0.22108 (14)	0.0385 (3)
C7	0.0394 (3)	0.5618 (2)	0.35388 (16)	0.0574 (5)
H7A	0.1299	0.6097	0.3812	0.086*
H7B	0.0352	0.4802	0.3936	0.086*
H7C	−0.0560	0.6095	0.3701	0.086*
C8	−0.0901 (2)	0.44394 (19)	0.05613 (18)	0.0536 (4)
H8A	−0.1817	0.3918	0.0356	0.064*
H8B	0.0051	0.3987	0.0311	0.064*
C9	−0.1001 (3)	0.5740 (2)	−0.00463 (18)	0.0630 (5)
H9A	−0.0978	0.5624	−0.0893	0.076*
H9B	−0.1990	0.6164	0.0161	0.076*
C10	0.0403 (2)	0.6562 (2)	0.03398 (18)	0.0574 (5)
H10A	0.1370	0.6202	0.0009	0.069*
H10B	0.0274	0.7424	0.0022	0.069*

	U11	U22	U33	U12	U13	U23
N1	0.0406 (7)	0.0382 (6)	0.0631 (9)	0.0007 (6)	0.0038 (7)	0.0057 (6)
C1	0.0532 (10)	0.0419 (8)	0.0737 (12)	0.0105 (8)	0.0012 (9)	0.0040 (9)
N2	0.0480 (7)	0.0342 (6)	0.0602 (8)	0.0046 (6)	0.0084 (7)	0.0023 (6)
C2	0.0406 (8)	0.0658 (11)	0.0594 (10)	0.0145 (8)	0.0010 (7)	−0.0043 (9)
N3	0.0321 (6)	0.0439 (7)	0.0549 (8)	−0.0012 (5)	0.0053 (5)	0.0062 (7)
C3	0.0340 (7)	0.0649 (10)	0.0564 (9)	−0.0048 (7)	0.0033 (7)	−0.0035 (9)
C4	0.0388 (7)	0.0425 (7)	0.0522 (9)	−0.0059 (6)	0.0040 (6)	−0.0022 (7)
C5	0.0340 (7)	0.0353 (7)	0.0400 (7)	−0.0006 (6)	0.0011 (6)	−0.0017 (6)
C6	0.0371 (7)	0.0359 (7)	0.0427 (7)	0.0006 (6)	0.0067 (6)	0.0007 (6)
C7	0.0614 (11)	0.0643 (11)	0.0466 (9)	0.0089 (9)	0.0088 (8)	−0.0057 (8)
C8	0.0415 (8)	0.0590 (10)	0.0603 (10)	−0.0022 (8)	−0.0019 (7)	−0.0084 (8)
C9	0.0568 (11)	0.0812 (13)	0.0509 (10)	0.0073 (10)	−0.0036 (8)	0.0088 (10)
C10	0.0591 (10)	0.0551 (9)	0.0579 (10)	0.0062 (9)	0.0097 (9)	0.0181 (9)

N1—C1	1.340 (2)	C4—H4	0.9300
N1—C5	1.339 (2)	C5—C6	1.539 (2)
C1—C2	1.374 (3)	C6—C7	1.532 (2)
C1—H1	0.9300	C7—H7A	0.9600
N2—C10	1.469 (3)	C7—H7B	0.9600
N2—C6	1.464 (2)	C7—H7C	0.9600
N2—H2A	0.89 (3)	C8—C9	1.517 (3)
C2—C3	1.375 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
N3—C6	1.468 (2)	C9—C10	1.521 (3)
N3—C8	1.464 (3)	C9—H9A	0.9700
N3—H3A	0.88 (3)	C9—H9B	0.9700
C3—C4	1.384 (2)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—C5	1.389 (2)
C1—N1—C5	117.95 (14)	N2—C6—C5	109.60 (12)
N1—C1—C2	123.75 (16)	C7—C6—C5	107.30 (14)
N1—C1—H1	118.1	C6—C7—H7A	109.5
C2—C1—H1	118.1	C6—C7—H7B	109.5
C10—N2—C6	113.21 (14)	H7A—C7—H7B	109.5
C10—N2—H2A	105.3 (17)	C6—C7—H7C	109.5
C6—N2—H2A	108.1 (16)	H7A—C7—H7C	109.5
C3—C2—C1	118.18 (16)	H7B—C7—H7C	109.5
C3—C2—H2	120.9	N3—C8—C9	108.52 (16)
C1—C2—H2	120.9	N3—C8—H8A	110.0
C6—N3—C8	112.72 (13)	C9—C8—H8A	110.0
C6—N3—H3A	109.1 (16)	N3—C8—H8B	110.0
C8—N3—H3A	110.1 (16)	C9—C8—H8B	110.0
C2—C3—C4	119.15 (16)	H8A—C8—H8B	108.4
C2—C3—H3	120.4	C10—C9—C8	108.91 (16)
C4—C3—H3	120.4	C10—C9—H9A	109.9
C5—C4—C3	119.22 (16)	C8—C9—H9A	109.9
C5—C4—H4	120.4	C10—C9—H9B	109.9
C3—C4—H4	120.4	C8—C9—H9B	109.9
N1—C5—C4	121.74 (15)	H9A—C9—H9B	108.3
N1—C5—C6	115.44 (13)	N2—C10—C9	113.65 (16)
C4—C5—C6	122.65 (13)	N2—C10—H10A	108.8
N3—C6—N2	110.72 (13)	C9—C10—H10A	108.8
N3—C6—C7	107.56 (13)	N2—C10—H10B	108.8
N2—C6—C7	108.46 (14)	C9—C10—H10B	108.8
N3—C6—C5	113.03 (12)	H10A—C10—H10B	107.7

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.89 (3)	2.31 (3)	3.188 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.89 (3)	2.31 (3)	3.188 (2)	168 (2)

Symmetry code: (i) .