2-Phenyl-2-(pyridin-2-yl)hexahydro-pyrimidine.

The title compound, C(15)H(17)N(3), was prepared by reaction of benzoyl-pyridine and hexahydropyrimidine. The 1,3-diazinane ring adopts a chair conformation with one N-H group axial and the other equatorial. The axial N-H group participates in very weak hydrogen bonding to the lone pair of electrons of the N atom with the equatorial H atom producing a very weakly hydrogen-bonded dimer. The pyridine N atom accepts an inter-nal hydrogen bond from the equatorial H atom. The phenyl ring adopts an equatorial position while the pyridine ring is axial. The phenyl ring exhibits a slight twist (ca 25°) relative to the hexahydropyrimidine ring. The pyridine ring stacks with symmetry-related pyridine rings.

Related literature

For recent reports of the structures of other hexahydropyrimidines, see: Al-Resayes (2009 ▶); Song et al. (2010 ▶) and references therein. For general structural parameters for organic mol­ecules, see: Allen et al. (1987 ▶). For the extinction correction, see: Zachariasen (1968 ▶).

Experimental

Crystal data

C15H17N3

M = 239.32

Triclinic,

a = 8.2173 (2) Å

b = 9.0211 (2) Å

c = 9.1481 (3) Å

α = 97.277 (1)°

β = 94.216 (1)°

γ = 112.036 (1)°

V = 618.11 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.61 mm−1

T = 90 K

0.31 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.823, T max = 0.897

6458 measured reflections

2159 independent reflections

1992 reflections with I > 3σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.166

S = 1.03

2159 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: TEXSAN for Windows (Molecular Structure Corporation, 1999 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: TEXSAN for Windows.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045976/fl2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045976/fl2327Isup2.hkl

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

C15H17N3	Z = 2
Mr = 239.32	F(000) = 256.00
Triclinic, P1	Dx = 1.286 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 8.2173 (2) Å	Cell parameters from 5072 reflections
b = 9.0211 (2) Å	θ = 4.9–68.4°
c = 9.1481 (3) Å	µ = 0.61 mm−1
α = 97.277 (1)°	T = 90 K
β = 94.216 (1)°	Fragment, colorless
γ = 112.036 (1)°	0.31 × 0.24 × 0.22 mm
V = 618.11 (3) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	2159 independent reflections
Radiation source: fine-focus sealed tube	2159 reflections with I > 10σ(I)
graphite	Rint = 0.022
ω and φ scans	θmax = 68.4°, θmin = 4.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.823, Tmax = 0.897	k = −10→10
6458 measured reflections	l = −10→10

Refinement on F2	0 constraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049	Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00563|Fo|2]
wR(F2) = 0.166	(Δ/σ)max = 0.010
S = 1.02	Δρmax = 0.27 e Å−3
2159 reflections	Δρmin = −0.18 e Å−3
169 parameters	Extinction correction: Zachariasen (1968), equ(3) Acta Cryst.(1968) A24, p. 213
0 restraints	Extinction coefficient: 0.000012 (5)

Refinement. Refinement of F2. The weighted R-factor wR and goodness of fit are based on F2, conventional R-factors R are based on F. R-factors based on F2 are statistically about twice as large as those based on F.

	x	y	z	Uiso*/Ueq
N1	0.25511 (12)	0.17532 (11)	0.94163 (10)	0.0178 (2)
N2	0.30025 (12)	0.06793 (11)	0.55486 (10)	0.0164 (3)
N3	0.51826 (11)	0.16009 (11)	0.77508 (11)	0.0160 (2)
C1	0.1439 (2)	0.2173 (1)	1.02090 (13)	0.0193 (3)
C2	−0.0223 (1)	0.20332 (13)	0.96108 (13)	0.0190 (3)
C3	−0.07658 (13)	0.14186 (13)	0.81117 (13)	0.0186 (3)
C4	0.0366 (1)	0.09780 (13)	0.72750 (12)	0.0167 (3)
C5	0.2016 (1)	0.11659 (12)	0.79702 (12)	0.0147 (3)
C6	0.33262 (13)	0.06232 (13)	0.71334 (12)	0.0150 (3)
C7	0.28971 (13)	−0.11566 (13)	0.72936 (12)	0.0145 (3)
C8	0.1246 (1)	−0.23417 (13)	0.66514 (12)	0.0175 (3)
C9	0.0792 (1)	−0.39534 (13)	0.68074 (12)	0.0193 (3)
C10	0.1985 (2)	−0.44127 (13)	0.76044 (13)	0.0205 (3)
C11	0.3625 (1)	−0.3247 (1)	0.82420 (12)	0.0197 (3)
C12	0.4078 (1)	−0.16293 (13)	0.80897 (12)	0.0173 (3)
C13	0.3650 (2)	0.2339 (1)	0.52058 (12)	0.0187 (3)
C14	0.5560 (1)	0.33528 (13)	0.58810 (13)	0.0207 (3)
C15	0.5755 (1)	0.32995 (13)	0.75312 (13)	0.0185 (3)
H1	0.1808	0.2589	1.1238	0.023*
H2	−0.0969	0.2351	1.0213	0.023*
H3	−0.1898	0.1301	0.7665	0.022*
H4	0.0025	0.0555	0.6245	0.020*
H5	0.0428	−0.2038	0.6103	0.021*
H6	−0.0333	−0.4744	0.6370	0.023*
H7	0.1679	−0.5515	0.7711	0.025*
H8	0.4444	−0.3555	0.8786	0.024*
H9	0.5202	−0.0841	0.8533	0.021*
H10	0.3572	0.2277	0.4157	0.023*
H11	0.2919	0.2860	0.5582	0.023*
H12	0.6325	0.2926	0.5417	0.025*
H13	0.5862	0.4443	0.5733	0.025*
H14	0.5040	0.3781	0.8004	0.022*
H15	0.6958	0.3878	0.7947	0.022*
H16	0.521 (2)	0.160 (2)	0.874 (2)	0.016*
H17	0.350 (2)	0.008 (2)	0.503 (2)	0.016*

	U11	U22	U33	U12	U13	U23
N1	0.0186 (5)	0.0184 (5)	0.0161 (5)	0.0069 (4)	0.0032 (4)	0.0029 (4)
N2	0.0170 (5)	0.0190 (5)	0.0150 (5)	0.0088 (4)	0.0049 (4)	0.0020 (4)
N3	0.0135 (5)	0.0165 (5)	0.0171 (5)	0.0051 (4)	0.0017 (4)	0.0022 (4)
C1	0.0217 (6)	0.0206 (5)	0.0157 (6)	0.0080 (5)	0.0058 (5)	0.0021 (4)
C2	0.0181 (5)	0.0179 (5)	0.0234 (6)	0.0080 (4)	0.0099 (5)	0.0046 (5)
C3	0.0154 (5)	0.0172 (5)	0.0236 (6)	0.0058 (4)	0.0048 (5)	0.0049 (5)
C4	0.0162 (5)	0.0155 (5)	0.0173 (6)	0.0048 (4)	0.0028 (4)	0.0028 (4)
C5	0.0147 (5)	0.0129 (5)	0.0167 (6)	0.0047 (4)	0.0048 (4)	0.0036 (4)
C6	0.0118 (5)	0.0167 (6)	0.0158 (6)	0.0050 (4)	0.0017 (4)	0.0021 (4)
C7	0.0140 (5)	0.0172 (6)	0.0129 (5)	0.0064 (4)	0.0059 (4)	0.0012 (4)
C8	0.0166 (6)	0.0211 (6)	0.0144 (6)	0.0074 (5)	0.0045 (4)	0.0005 (5)
C9	0.0164 (5)	0.0206 (6)	0.0166 (6)	0.0031 (5)	0.0060 (4)	−0.0014 (5)
C10	0.0268 (6)	0.0153 (5)	0.0193 (6)	0.0073 (5)	0.0097 (5)	0.0020 (4)
C11	0.0220 (6)	0.0215 (6)	0.0192 (6)	0.0118 (5)	0.0064 (5)	0.0035 (5)
C12	0.0166 (5)	0.0191 (6)	0.0160 (6)	0.0071 (5)	0.0042 (5)	0.0010 (5)
C13	0.0189 (6)	0.0231 (6)	0.0183 (6)	0.0107 (5)	0.0071 (5)	0.0071 (5)
C14	0.0191 (6)	0.0192 (6)	0.0261 (7)	0.0081 (5)	0.0092 (5)	0.0071 (5)
C15	0.0144 (5)	0.0162 (5)	0.0254 (6)	0.0058 (4)	0.0051 (5)	0.0038 (5)

N1—C1	1.339 (2)	C7—C8	1.401 (1)
N1—C5	1.337 (2)	C8—H5	0.95
N2—H17	0.91 (1)	C8—C9	1.388 (2)
N2—C6	1.465 (1)	C9—H6	0.95
N2—C13	1.4730 (13)	C9—C10	1.393 (2)
N3—H16	0.90 (1)	C10—H7	0.95
N3—C6	1.4702 (12)	C10—C11	1.388 (2)
N3—C15	1.4699 (13)	C11—H8	0.95
C1—H1	0.95	C11—C12	1.393 (2)
C1—C2	1.387 (2)	C12—H9	0.95
C2—H2	0.95	C13—H10	0.95
C2—C3	1.385 (2)	C13—H11	0.95
C3—H3	0.95	C13—C14	1.523 (1)
C3—C4	1.383 (2)	C14—H13	0.95
C4—H4	0.95	C14—H12	0.95
C4—C5	1.395 (2)	C14—C15	1.515 (2)
C5—C6	1.551 (1)	C15—H15	0.95
C6—C7	1.538 (1)	C15—H14	0.95
C7—C12	1.392 (2)
N1···C11i	3.373 (1)	N3···C3iv	3.389 (1)
N1···C2ii	3.498 (2)	C1···C2ii	3.572 (2)
N1···C12i	3.501 (2)	C2···C8ii	3.582 (2)
N2···C4iii	3.381 (2)	C9···C9v	3.484 (2)
C5—N1—C1	117.65 (9)	H5—C8—C7	119.6
H17—N2—C6	108.9 (8)	C9—C8—C7	120.82 (10)
H17—N2—C13	110.7 (8)	H6—C9—C8	120.0
C6—N2—C13	113.36 (8)	H6—C9—C10	120.0
H16—N3—C6	104.7 (8)	C8—C9—C10	120.06 (10)
H16—N3—C15	107.2 (8)	H7—C10—C11	120.2
C6—N3—C15	112.82 (9)	H7—C10—C9	120.2
H1—C1—N1	118.2	C11—C10—C9	119.5 (1)
H1—C1—C2	118.2	H8—C11—C10	119.8
N1—C1—C2	123.62 (10)	H8—C11—C12	119.8
H2—C2—C3	120.9	C10—C11—C12	120.40 (10)
H2—C2—C1	120.9	H9—C12—C7	119.7
C3—C2—C1	118.23 (10)	H9—C12—C11	119.7
H3—C3—C4	120.5	C7—C12—C11	120.60 (10)
H3—C3—C2	120.5	H10—C13—H11	109.5
C4—C3—C2	118.97 (10)	H10—C13—N2	108.6
H4—C4—C3	120.6	H10—C13—C14	108.6
H4—C4—C5	120.6	H11—C13—N2	108.6
C3—C4—C5	118.85 (10)	H11—C13—C14	108.6
N1—C5—C4	122.68 (10)	N2—C13—C14	113.03 (9)
N1—C5—C6	115.06 (9)	H13—C14—H12	109.5
C4—C5—C6	122.19 (9)	H13—C14—C15	109.5
N2—C6—N3	111.48 (9)	H13—C14—C13	109.5
N2—C6—C7	107.67 (8)	H12—C14—C15	109.5
N2—C6—C5	109.10 (8)	H12—C14—C13	109.5
N3—C6—C7	109.07 (9)	C15—C14—C13	109.24 (9)
N3—C6—C5	112.26 (8)	H15—C15—H14	109.5
C7—C6—C5	107.06 (8)	H15—C15—N3	109.6
C12—C7—C8	118.61 (10)	H15—C15—C14	109.6
C12—C7—C6	122.22 (10)	H14—C15—N3	109.6
C8—C7—C6	119.15 (10)	H14—C15—C14	109.6
H5—C8—C9	119.6	N3—C15—C14	109.21 (9)
N1—C1—C2—C3	0.3 (2)	C2—C3—C4—C5	0.1 (2)
N1—C5—C4—C3	0.1 (2)	C3—C4—C5—C6	176.89 (9)
N1—C5—C6—N2	−155.92 (9)	C4—C5—C6—C7	−89.2 (1)
N1—C5—C6—N3	−31.8 (1)	C5—C6—N2—C13	74.1 (1)
N1—C5—C6—C7	87.8 (1)	C5—C6—N3—C15	−66.4 (1)
N2—C6—N3—C15	56.4 (1)	C5—C6—C7—C8	64.4 (1)
N2—C6—C5—C4	27.1 (1)	C5—C6—C7—C12	−114.0 (1)
N2—C6—C7—C8	−52.8 (1)	C6—N2—C13—C14	50.1 (1)
N2—C6—C7—C12	128.9 (1)	C6—N3—C15—C14	−60.0 (1)
N2—C13—C14—C15	−52.8 (1)	C6—C7—C8—C9	−178.20 (8)
N3—C6—N2—C13	−50.5 (1)	C6—C7—C12—C11	178.39 (9)
N3—C6—C5—C4	151.2 (1)	C7—C6—N2—C13	−170.05 (8)
N3—C6—C7—C8	−173.95 (9)	C7—C6—N3—C15	175.14 (8)
N3—C6—C7—C12	7.7 (1)	C7—C8—C9—C10	−0.3 (2)
N3—C15—C14—C13	56.7 (1)	C7—C12—C11—C10	−0.2 (2)
C1—N1—C5—C4	−0.1 (2)	C8—C7—C12—C11	0.1 (2)
C1—N1—C5—C6	−177.08 (9)	C8—C9—C10—C11	0.2 (2)
C1—C2—C3—C4	−0.3 (2)	C9—C8—C7—C12	0.2 (2)
C2—C1—N1—C5	−0.1 (2)	C9—C10—C11—C12	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H16···N1	0.90 (1)	2.365 (13)	2.7696 (12)	107.1 (10)
N2—H17···N3vi	0.91 (1)	3.25 (1)	4.1179 (13)	160.2 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H16⋯N1	0.90 (1)	2.365 (13)	2.7696 (12)	107.1 (10)
N2—H17⋯N3i	0.91 (1)	3.25 (1)	4.1179 (13)	160.2 (10)

Symmetry code: (i) .