N-tert-Butyl-2-[4-(dimethyl-amino)-phen-yl]imidazo[1,2-a]pyrazin-3-amine.

In the title compound, C18H23N5, the imidazole ring makes a dihedral angles of 3.96 (8) and 19.02 (8)°, respectively, with the pyrazine and benzene rings while the dihedral angle between the pyrazine and benzene rings is 16.96 (7)°. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains along [010]. These chains are linked by C-H⋯N hydrogen bonds, forming two-dimensional networks lying parallel to (001).

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 ▶); Dubinina et al. (2006 ▶); Ellsworth et al. (2007 ▶); Mukaiyama et al. (2007 ▶). For ongoing structural studies of heterocyclic N-containing derivatives, see: Nasir et al. (2010 ▶). For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶). For general background to the use of imidazole derivatives as drugs, see: Dooley et al. (1992 ▶); Jackson et al. (2000 ▶); Banfi et al. (2006 ▶). For a related structure, see: Ouzidan et al. (2011 ▶).

Experimental

Crystal data

C18H23N5

M = 309.41

Orthorhombic,

a = 12.1746 (11) Å

b = 13.9614 (13) Å

c = 20.2985 (19) Å

V = 3450.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.978, T max = 0.985

18314 measured reflections

4157 independent reflections

2964 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.148

S = 1.03

4157 reflections

218 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007861/su2577sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007861/su2577Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007861/su2577Isup3.cml

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

C18H23N5	F(000) = 1328
Mr = 309.41	Dx = 1.191 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4157 reflections
a = 12.1746 (11) Å	θ = 2.0–28.3°
b = 13.9614 (13) Å	µ = 0.07 mm−1
c = 20.2985 (19) Å	T = 293 K
V = 3450.2 (6) Å3	Block, colourless
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	4157 independent reflections
Radiation source: fine-focus sealed tube	2964 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω and φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→16
Tmin = 0.978, Tmax = 0.985	k = −18→17
18314 measured reflections	l = −16→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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.8061P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4157 reflections	Δρmax = 0.32 e Å−3
218 parameters	Δρmin = −0.25 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: 0.0055 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	−0.08078 (14)	−0.06634 (12)	0.30835 (9)	0.0504 (4)
H1	−0.1275	−0.0743	0.3442	0.060*
C2	−0.01406 (13)	0.01078 (11)	0.30790 (8)	0.0435 (4)
H2	−0.0140	0.0542	0.3427	0.052*
C3	0.04911 (13)	−0.03960 (10)	0.20176 (7)	0.0402 (3)
C4	−0.01999 (15)	−0.11940 (11)	0.20827 (9)	0.0506 (4)
H4	−0.0206	−0.1646	0.1746	0.061*
C5	0.12824 (11)	0.09448 (10)	0.23825 (7)	0.0343 (3)
C6	0.16191 (11)	0.07218 (10)	0.17397 (7)	0.0340 (3)
C7	0.23754 (11)	0.12262 (10)	0.12939 (7)	0.0337 (3)
C8	0.28253 (13)	0.07449 (10)	0.07535 (7)	0.0397 (3)
H8	0.2628	0.0110	0.0680	0.048*
C9	0.35502 (14)	0.11775 (12)	0.03267 (7)	0.0455 (4)
H9	0.3843	0.0825	−0.0020	0.055*
C10	0.38571 (12)	0.21406 (11)	0.04048 (7)	0.0405 (3)
C11	0.33674 (12)	0.26364 (11)	0.09300 (7)	0.0396 (3)
H11	0.3524	0.3283	0.0988	0.047*
C12	0.26608 (12)	0.21882 (10)	0.13617 (7)	0.0375 (3)
H12	0.2365	0.2538	0.1709	0.045*
C13	0.51820 (19)	0.20205 (17)	−0.05008 (11)	0.0752 (6)
H13A	0.5585	0.1523	−0.0281	0.113*
H13B	0.5684	0.2428	−0.0734	0.113*
H13C	0.4674	0.1740	−0.0806	0.113*
C14	0.48781 (18)	0.35712 (15)	0.00500 (10)	0.0670 (5)
H14A	0.4222	0.3952	0.0070	0.101*
H14B	0.5314	0.3768	−0.0320	0.101*
H14C	0.5292	0.3657	0.0448	0.101*
C15	0.24118 (15)	0.15682 (14)	0.33195 (8)	0.0528 (4)
C16	0.34950 (17)	0.1809 (3)	0.29967 (13)	0.1029 (10)
H16A	0.3616	0.1387	0.2631	0.154*
H16B	0.4078	0.1734	0.3311	0.154*
H16C	0.3479	0.2460	0.2843	0.154*
C17	0.2179 (2)	0.2255 (2)	0.38729 (11)	0.0970 (9)
H17A	0.2182	0.2898	0.3707	0.146*
H17B	0.2733	0.2190	0.4206	0.146*
H17C	0.1472	0.2114	0.4059	0.146*
C18	0.2491 (3)	0.0546 (2)	0.35636 (17)	0.1255 (13)
H18A	0.1877	0.0409	0.3845	0.188*
H18B	0.3162	0.0464	0.3806	0.188*
H18C	0.2484	0.0116	0.3195	0.188*
N1	−0.08393 (13)	−0.13359 (9)	0.25942 (8)	0.0540 (4)
N2	0.05405 (10)	0.02334 (8)	0.25439 (6)	0.0364 (3)
N3	0.14805 (10)	0.16613 (9)	0.28437 (6)	0.0393 (3)
N4	0.11341 (11)	−0.01085 (9)	0.15268 (6)	0.0417 (3)
N5	0.45877 (13)	0.25768 (12)	−0.00212 (7)	0.0601 (4)
H3	0.1442 (13)	0.2223 (13)	0.2656 (8)	0.042 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0562 (10)	0.0418 (9)	0.0532 (9)	0.0031 (7)	0.0173 (8)	0.0078 (7)
C2	0.0505 (9)	0.0407 (8)	0.0394 (7)	0.0067 (7)	0.0083 (7)	0.0017 (6)
C3	0.0444 (8)	0.0323 (7)	0.0440 (8)	0.0002 (6)	0.0063 (7)	−0.0035 (6)
C4	0.0567 (10)	0.0364 (8)	0.0586 (10)	−0.0068 (7)	0.0142 (8)	−0.0076 (7)
C5	0.0361 (7)	0.0293 (7)	0.0375 (7)	0.0033 (6)	−0.0007 (6)	0.0002 (5)
C6	0.0340 (7)	0.0296 (7)	0.0385 (7)	0.0035 (5)	0.0007 (6)	−0.0020 (5)
C7	0.0322 (7)	0.0343 (7)	0.0345 (7)	0.0021 (5)	−0.0015 (5)	−0.0002 (6)
C8	0.0467 (8)	0.0332 (7)	0.0392 (7)	−0.0001 (6)	0.0016 (6)	−0.0043 (6)
C9	0.0532 (9)	0.0448 (9)	0.0384 (7)	0.0022 (7)	0.0086 (7)	−0.0059 (7)
C10	0.0369 (7)	0.0467 (9)	0.0379 (7)	−0.0026 (6)	−0.0001 (6)	0.0016 (6)
C11	0.0402 (7)	0.0366 (8)	0.0419 (7)	−0.0045 (6)	−0.0010 (6)	−0.0017 (6)
C12	0.0392 (7)	0.0352 (7)	0.0379 (7)	0.0011 (6)	0.0010 (6)	−0.0056 (6)
C13	0.0726 (14)	0.0869 (16)	0.0662 (12)	0.0015 (11)	0.0331 (11)	0.0044 (11)
C14	0.0725 (13)	0.0677 (12)	0.0610 (11)	−0.0256 (10)	0.0065 (10)	0.0113 (9)
C15	0.0494 (9)	0.0655 (11)	0.0434 (8)	0.0067 (8)	−0.0102 (7)	−0.0113 (8)
C16	0.0460 (12)	0.188 (3)	0.0746 (14)	0.0117 (15)	−0.0093 (11)	−0.0300 (17)
C17	0.0787 (15)	0.146 (3)	0.0659 (13)	0.0234 (16)	−0.0176 (12)	−0.0533 (15)
C18	0.147 (3)	0.091 (2)	0.138 (3)	0.0072 (19)	−0.092 (2)	0.0259 (18)
N1	0.0589 (9)	0.0375 (7)	0.0657 (9)	−0.0044 (6)	0.0185 (7)	0.0017 (7)
N2	0.0390 (6)	0.0311 (6)	0.0392 (6)	0.0031 (5)	0.0039 (5)	0.0009 (5)
N3	0.0445 (7)	0.0354 (7)	0.0378 (6)	0.0047 (5)	−0.0024 (5)	−0.0055 (5)
N4	0.0472 (7)	0.0340 (6)	0.0439 (7)	−0.0049 (5)	0.0072 (6)	−0.0060 (5)
N5	0.0613 (9)	0.0632 (9)	0.0557 (8)	−0.0138 (8)	0.0211 (7)	−0.0013 (7)

C1—C2	1.349 (2)	C11—H11	0.9300
C1—N1	1.367 (2)	C12—H12	0.9300
C1—H1	0.9300	C13—N5	1.440 (2)
C2—N2	1.3778 (19)	C13—H13A	0.9600
C2—H2	0.9300	C13—H13B	0.9600
C3—N4	1.3291 (19)	C13—H13C	0.9600
C3—N2	1.3847 (18)	C14—N5	1.440 (2)
C3—C4	1.402 (2)	C14—H14A	0.9600
C4—N1	1.313 (2)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—N2	1.3819 (18)	C15—N3	1.495 (2)
C5—N3	1.3912 (18)	C15—C17	1.504 (3)
C5—C6	1.4027 (19)	C15—C16	1.510 (3)
C6—N4	1.3709 (18)	C15—C18	1.514 (3)
C6—C7	1.4706 (19)	C16—H16A	0.9600
C7—C12	1.394 (2)	C16—H16B	0.9600
C7—C8	1.398 (2)	C16—H16C	0.9600
C8—C9	1.376 (2)	C17—H17A	0.9600
C8—H8	0.9300	C17—H17B	0.9600
C9—C10	1.405 (2)	C17—H17C	0.9600
C9—H9	0.9300	C18—H18A	0.9600
C10—N5	1.382 (2)	C18—H18B	0.9600
C10—C11	1.404 (2)	C18—H18C	0.9600
C11—C12	1.378 (2)	N3—H3	0.873 (17)
C2—C1—N1	124.07 (15)	N5—C14—H14A	109.5
C2—C1—H1	118.0	N5—C14—H14B	109.5
N1—C1—H1	118.0	H14A—C14—H14B	109.5
C1—C2—N2	118.00 (14)	N5—C14—H14C	109.5
C1—C2—H2	121.0	H14A—C14—H14C	109.5
N2—C2—H2	121.0	H14B—C14—H14C	109.5
N4—C3—N2	111.17 (13)	N3—C15—C17	106.49 (15)
N4—C3—C4	131.60 (14)	N3—C15—C16	111.26 (15)
N2—C3—C4	117.23 (13)	C17—C15—C16	110.3 (2)
N1—C4—C3	123.38 (15)	N3—C15—C18	109.98 (17)
N1—C4—H4	118.3	C17—C15—C18	111.6 (2)
C3—C4—H4	118.3	C16—C15—C18	107.2 (2)
N2—C5—N3	118.08 (12)	C15—C16—H16A	109.5
N2—C5—C6	104.60 (12)	C15—C16—H16B	109.5
N3—C5—C6	137.30 (13)	H16A—C16—H16B	109.5
N4—C6—C5	110.80 (12)	C15—C16—H16C	109.5
N4—C6—C7	118.73 (12)	H16A—C16—H16C	109.5
C5—C6—C7	130.48 (13)	H16B—C16—H16C	109.5
C12—C7—C8	116.29 (13)	C15—C17—H17A	109.5
C12—C7—C6	123.82 (12)	C15—C17—H17B	109.5
C8—C7—C6	119.86 (13)	H17A—C17—H17B	109.5
C9—C8—C7	122.29 (14)	C15—C17—H17C	109.5
C9—C8—H8	118.9	H17A—C17—H17C	109.5
C7—C8—H8	118.9	H17B—C17—H17C	109.5
C8—C9—C10	121.30 (14)	C15—C18—H18A	109.5
C8—C9—H9	119.3	C15—C18—H18B	109.5
C10—C9—H9	119.3	H18A—C18—H18B	109.5
N5—C10—C11	122.09 (14)	C15—C18—H18C	109.5
N5—C10—C9	121.49 (14)	H18A—C18—H18C	109.5
C11—C10—C9	116.41 (13)	H18B—C18—H18C	109.5
C12—C11—C10	121.61 (14)	C4—N1—C1	117.02 (14)
C12—C11—H11	119.2	C2—N2—C5	132.20 (13)
C10—C11—H11	119.2	C2—N2—C3	120.09 (13)
C11—C12—C7	122.01 (13)	C5—N2—C3	107.56 (12)
C11—C12—H12	119.0	C5—N3—C15	120.24 (12)
C7—C12—H12	119.0	C5—N3—H3	110.0 (11)
N5—C13—H13A	109.5	C15—N3—H3	113.6 (11)
N5—C13—H13B	109.5	C3—N4—C6	105.83 (12)
H13A—C13—H13B	109.5	C10—N5—C14	121.33 (15)
N5—C13—H13C	109.5	C10—N5—C13	120.58 (16)
H13A—C13—H13C	109.5	C14—N5—C13	117.68 (16)
H13B—C13—H13C	109.5
N1—C1—C2—N2	1.0 (3)	C1—C2—N2—C5	177.97 (15)
N4—C3—C4—N1	−175.41 (17)	C1—C2—N2—C3	3.0 (2)
N2—C3—C4—N1	4.2 (3)	N3—C5—N2—C2	5.3 (2)
N2—C5—C6—N4	−2.09 (16)	C6—C5—N2—C2	−173.15 (14)
N3—C5—C6—N4	179.96 (16)	N3—C5—N2—C3	−179.30 (12)
N2—C5—C6—C7	178.06 (14)	C6—C5—N2—C3	2.27 (15)
N3—C5—C6—C7	0.1 (3)	N4—C3—N2—C2	174.29 (13)
N4—C6—C7—C12	160.24 (13)	C4—C3—N2—C2	−5.4 (2)
C5—C6—C7—C12	−19.9 (2)	N4—C3—N2—C5	−1.79 (17)
N4—C6—C7—C8	−17.7 (2)	C4—C3—N2—C5	178.51 (14)
C5—C6—C7—C8	162.11 (14)	N2—C5—N3—C15	93.24 (17)
C12—C7—C8—C9	2.9 (2)	C6—C5—N3—C15	−89.0 (2)
C6—C7—C8—C9	−178.96 (14)	C17—C15—N3—C5	−161.45 (18)
C7—C8—C9—C10	−1.5 (2)	C16—C15—N3—C5	78.3 (2)
C8—C9—C10—N5	179.77 (15)	C18—C15—N3—C5	−40.4 (2)
C8—C9—C10—C11	−1.3 (2)	N2—C3—N4—C6	0.46 (17)
N5—C10—C11—C12	−178.37 (15)	C4—C3—N4—C6	−179.89 (17)
C9—C10—C11—C12	2.7 (2)	C5—C6—N4—C3	1.04 (16)
C10—C11—C12—C7	−1.3 (2)	C7—C6—N4—C3	−179.08 (13)
C8—C7—C12—C11	−1.5 (2)	C11—C10—N5—C14	−0.5 (3)
C6—C7—C12—C11	−179.53 (14)	C9—C10—N5—C14	178.34 (17)
C3—C4—N1—C1	−0.5 (3)	C11—C10—N5—C13	171.93 (17)
C2—C1—N1—C4	−2.2 (3)	C9—C10—N5—C13	−9.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1i	0.873 (18)	2.201 (18)	3.0361 (18)	160.0 (14)
C11—H11···N4ii	0.93	2.53	3.428 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1i	0.873 (18)	2.201 (18)	3.0361 (18)	160.0 (14)
C11—H11⋯N4ii	0.93	2.53	3.428 (2)	162

Symmetry codes: (i) ; (ii) .