N-{4-[3-(4-Fluoro-phen-yl)pyrido[2,3-b]pyrazin-2-yl]-2-pyrid-yl}isopropyl-amine.

In the crystal structure of the title compound, C(21)H(18)FN(5), the pyridopyrazine ring system forms dihedral angles of 33.27 (7) and 48.69 (9)° with the 4-fluoro-phenyl and pyridine ring, respectively. The dihedral angle of the 4-fluoro-phenyl and pyridine rings is 57.45 (8)°. The crystal packing is characterized by an inter-molecular N-H⋯N hydrogen bond.

Related literature

For the preparation of pyridopyrazines under microwave conditions, see: Zhao et al. (2004 ▶)

Experimental

Crystal data

C21H18FN5

M = 359.40

Monoclinic,

a = 12.042 (1) Å

b = 7.6586 (2) Å

c = 20.095 (2) Å

β = 100.215 (5)°

V = 1823.8 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 193 K

0.50 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.743, T max = 0.998

3578 measured reflections

3468 independent reflections

2912 reflections with I > 2σ(I)

R int = 0.063

3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.127

S = 1.05

3468 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038173/im2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038173/im2142Isup2.hkl

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

C21H18FN5	F(000) = 752
Mr = 359.40	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.042 (1) Å	θ = 60–69°
b = 7.6586 (2) Å	µ = 0.72 mm−1
c = 20.095 (2) Å	T = 193 K
β = 100.215 (5)°	Plate, yellow
V = 1823.8 (3) Å3	0.50 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2912 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.063
graphite	θmax = 70.2°, θmin = 3.7°
ω/2θ scans	h = −14→14
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = −9→0
Tmin = 0.743, Tmax = 0.998	l = 0→24
3578 measured reflections	3 standard reflections every 60 min
3468 independent reflections	intensity decay: 2%

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.065P)2 + 0.5513P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3468 reflections	Δρmax = 0.29 e Å−3
247 parameters	Δρmin = −0.28 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: 0.0038 (4)

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
F1	0.34953 (12)	0.36820 (19)	0.45738 (6)	0.0682 (4)
N1	0.47943 (11)	0.38937 (19)	0.08886 (7)	0.0343 (3)
C2	0.43429 (13)	0.4033 (2)	0.14386 (8)	0.0292 (3)
C3	0.50235 (12)	0.38498 (19)	0.21015 (8)	0.0278 (3)
N4	0.61263 (11)	0.36734 (17)	0.21777 (7)	0.0315 (3)
C5	0.66035 (13)	0.3611 (2)	0.16141 (8)	0.0319 (4)
N6	0.77471 (11)	0.3488 (2)	0.17218 (8)	0.0412 (4)
C7	0.82147 (15)	0.3384 (3)	0.11753 (10)	0.0463 (5)
H7	0.9014	0.3315	0.1237	0.056*
C8	0.76109 (16)	0.3370 (3)	0.05108 (10)	0.0508 (5)
H8	0.7998	0.3258	0.0140	0.061*
C9	0.64671 (16)	0.3516 (3)	0.04001 (9)	0.0470 (5)
H9	0.6042	0.3522	−0.0046	0.056*
C10	0.59296 (14)	0.3660 (2)	0.09677 (8)	0.0336 (4)
C11	0.31151 (12)	0.4444 (2)	0.13098 (7)	0.0287 (3)
C12	0.23734 (13)	0.3532 (2)	0.08126 (8)	0.0349 (4)
H12	0.2628	0.2571	0.0581	0.042*
C13	0.12700 (13)	0.4069 (2)	0.06713 (8)	0.0370 (4)
H13	0.0772	0.3442	0.0336	0.044*
N14	0.08393 (10)	0.54181 (18)	0.09720 (7)	0.0345 (3)
C15	0.15497 (13)	0.6273 (2)	0.14529 (8)	0.0307 (3)
C16	0.26989 (12)	0.5820 (2)	0.16339 (8)	0.0299 (3)
H16	0.3181	0.6456	0.1975	0.036*
N17	0.11431 (11)	0.76489 (19)	0.17634 (7)	0.0382 (4)
H17	0.1587	0.8153	0.2129	0.046*
C18	−0.00040 (14)	0.8299 (2)	0.15770 (9)	0.0393 (4)
H18	−0.0531	0.7279	0.1513	0.047*
C19	−0.02796 (18)	0.9414 (3)	0.21535 (11)	0.0545 (5)
H19A	−0.0258	0.8687	0.2557	0.082*
H19B	−0.1035	0.9917	0.2022	0.082*
H19C	0.0276	1.0356	0.2252	0.082*
C20	−0.0150 (2)	0.9323 (3)	0.09207 (11)	0.0610 (6)
H20A	0.0307	1.0388	0.0989	0.091*
H20B	−0.0947	0.9636	0.0780	0.091*
H20C	0.0094	0.8607	0.0569	0.091*
C21	0.45692 (13)	0.3816 (2)	0.27448 (8)	0.0295 (3)
C22	0.52397 (14)	0.4499 (2)	0.33258 (8)	0.0355 (4)
H22	0.5953	0.4994	0.3296	0.043*
C23	0.48813 (17)	0.4467 (2)	0.39438 (9)	0.0439 (4)
H23	0.5330	0.4955	0.4337	0.053*
C24	0.38569 (17)	0.3708 (3)	0.39702 (9)	0.0441 (4)
C25	0.31854 (15)	0.2973 (2)	0.34194 (9)	0.0410 (4)
H25	0.2491	0.2433	0.3460	0.049*
C26	0.35451 (14)	0.3039 (2)	0.28003 (8)	0.0342 (4)
H26	0.3088	0.2549	0.2411	0.041*

	U11	U22	U33	U12	U13	U23
F1	0.0892 (9)	0.0835 (9)	0.0395 (6)	−0.0090 (7)	0.0321 (6)	0.0019 (6)
N1	0.0320 (7)	0.0395 (8)	0.0321 (7)	0.0079 (6)	0.0075 (5)	0.0045 (6)
C2	0.0298 (8)	0.0263 (7)	0.0321 (8)	0.0022 (6)	0.0070 (6)	0.0014 (6)
C3	0.0282 (7)	0.0230 (7)	0.0322 (8)	0.0009 (6)	0.0054 (6)	0.0008 (6)
N4	0.0285 (7)	0.0311 (7)	0.0348 (7)	0.0033 (5)	0.0053 (5)	0.0024 (5)
C5	0.0292 (8)	0.0277 (8)	0.0399 (9)	0.0037 (6)	0.0091 (6)	0.0051 (6)
N6	0.0275 (7)	0.0448 (9)	0.0524 (9)	0.0048 (6)	0.0103 (6)	0.0048 (7)
C7	0.0305 (8)	0.0486 (11)	0.0634 (12)	0.0084 (8)	0.0181 (8)	0.0125 (9)
C8	0.0460 (10)	0.0590 (12)	0.0540 (11)	0.0162 (9)	0.0273 (9)	0.0193 (9)
C9	0.0438 (10)	0.0610 (12)	0.0395 (9)	0.0169 (9)	0.0164 (8)	0.0154 (9)
C10	0.0324 (8)	0.0325 (8)	0.0373 (8)	0.0085 (6)	0.0101 (6)	0.0074 (7)
C11	0.0279 (7)	0.0302 (8)	0.0285 (7)	0.0022 (6)	0.0066 (6)	0.0025 (6)
C12	0.0333 (8)	0.0360 (9)	0.0363 (8)	0.0011 (7)	0.0085 (6)	−0.0077 (7)
C13	0.0306 (8)	0.0409 (9)	0.0386 (9)	−0.0044 (7)	0.0037 (7)	−0.0099 (7)
N14	0.0259 (6)	0.0389 (8)	0.0383 (7)	0.0003 (5)	0.0045 (5)	−0.0038 (6)
C15	0.0288 (7)	0.0327 (8)	0.0311 (7)	0.0017 (6)	0.0073 (6)	0.0008 (6)
C16	0.0276 (7)	0.0307 (8)	0.0305 (7)	0.0006 (6)	0.0026 (6)	−0.0011 (6)
N17	0.0308 (7)	0.0410 (8)	0.0409 (8)	0.0088 (6)	0.0018 (6)	−0.0093 (6)
C18	0.0299 (8)	0.0371 (9)	0.0503 (10)	0.0077 (7)	0.0057 (7)	−0.0037 (8)
C19	0.0490 (11)	0.0553 (12)	0.0597 (12)	0.0199 (9)	0.0104 (9)	−0.0105 (10)
C20	0.0668 (14)	0.0562 (13)	0.0567 (13)	0.0236 (11)	0.0025 (10)	0.0048 (10)
C21	0.0318 (8)	0.0264 (8)	0.0306 (8)	0.0049 (6)	0.0068 (6)	0.0033 (6)
C22	0.0389 (9)	0.0327 (8)	0.0344 (8)	−0.0004 (7)	0.0051 (7)	0.0014 (7)
C23	0.0570 (11)	0.0424 (10)	0.0310 (8)	−0.0020 (8)	0.0044 (8)	−0.0006 (7)
C24	0.0588 (11)	0.0448 (10)	0.0323 (9)	0.0049 (9)	0.0183 (8)	0.0058 (7)
C25	0.0415 (9)	0.0400 (9)	0.0446 (10)	0.0005 (8)	0.0163 (7)	0.0077 (8)
C26	0.0351 (8)	0.0320 (8)	0.0360 (8)	0.0019 (7)	0.0076 (6)	0.0015 (7)

F1—C24	1.3595 (19)	C15—N17	1.359 (2)
N1—C2	1.3197 (19)	C15—C16	1.410 (2)
N1—C10	1.360 (2)	C16—H16	0.9500
C2—C3	1.442 (2)	N17—C18	1.454 (2)
C2—C11	1.489 (2)	N17—H17	0.9144
C3—N4	1.3165 (19)	C18—C20	1.518 (3)
C3—C21	1.491 (2)	C18—C19	1.523 (2)
N4—C5	1.359 (2)	C18—H18	1.0000
C5—N6	1.359 (2)	C19—H19A	0.9800
C5—C10	1.405 (2)	C19—H19B	0.9800
N6—C7	1.322 (2)	C19—H19C	0.9800
C7—C8	1.403 (3)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C8—C9	1.360 (3)	C20—H20C	0.9800
C8—H8	0.9500	C21—C26	1.391 (2)
C9—C10	1.412 (2)	C21—C22	1.398 (2)
C9—H9	0.9500	C22—C23	1.385 (2)
C11—C16	1.379 (2)	C22—H22	0.9500
C11—C12	1.403 (2)	C23—C24	1.373 (3)
C12—C13	1.372 (2)	C23—H23	0.9500
C12—H12	0.9500	C24—C25	1.370 (3)
C13—N14	1.346 (2)	C25—C26	1.389 (2)
C13—H13	0.9500	C25—H25	0.9500
N14—C15	1.342 (2)	C26—H26	0.9500
C2—N1—C10	117.88 (13)	C15—N17—C18	123.40 (14)
N1—C2—C3	120.98 (14)	C15—N17—H17	119.3
N1—C2—C11	114.55 (13)	C18—N17—H17	117.2
C3—C2—C11	124.44 (13)	N17—C18—C20	111.07 (15)
N4—C3—C2	120.92 (14)	N17—C18—C19	108.76 (15)
N4—C3—C21	114.53 (13)	C20—C18—C19	111.33 (16)
C2—C3—C21	124.54 (13)	N17—C18—H18	108.5
C3—N4—C5	118.27 (13)	C20—C18—H18	108.5
N4—C5—N6	115.86 (14)	C19—C18—H18	108.5
N4—C5—C10	120.63 (14)	C18—C19—H19A	109.5
N6—C5—C10	123.51 (15)	C18—C19—H19B	109.5
C7—N6—C5	116.14 (15)	H19A—C19—H19B	109.5
N6—C7—C8	124.47 (16)	C18—C19—H19C	109.5
N6—C7—H7	117.8	H19A—C19—H19C	109.5
C8—C7—H7	117.8	H19B—C19—H19C	109.5
C9—C8—C7	119.59 (17)	C18—C20—H20A	109.5
C9—C8—H8	120.2	C18—C20—H20B	109.5
C7—C8—H8	120.2	H20A—C20—H20B	109.5
C8—C9—C10	118.05 (17)	C18—C20—H20C	109.5
C8—C9—H9	121.0	H20A—C20—H20C	109.5
C10—C9—H9	121.0	H20B—C20—H20C	109.5
N1—C10—C5	121.04 (14)	C26—C21—C22	118.82 (15)
N1—C10—C9	120.74 (15)	C26—C21—C3	122.93 (14)
C5—C10—C9	118.19 (15)	C22—C21—C3	118.12 (14)
C16—C11—C12	118.58 (14)	C23—C22—C21	121.09 (16)
C16—C11—C2	120.82 (14)	C23—C22—H22	119.5
C12—C11—C2	120.37 (14)	C21—C22—H22	119.5
C13—C12—C11	117.96 (15)	C24—C23—C22	117.83 (16)
C13—C12—H12	121.0	C24—C23—H23	121.1
C11—C12—H12	121.0	C22—C23—H23	121.1
N14—C13—C12	124.99 (15)	F1—C24—C25	118.57 (17)
N14—C13—H13	117.5	F1—C24—C23	118.20 (17)
C12—C13—H13	117.5	C25—C24—C23	123.23 (16)
C15—N14—C13	116.76 (13)	C24—C25—C26	118.40 (16)
N14—C15—N17	118.24 (14)	C24—C25—H25	120.8
N14—C15—C16	122.48 (14)	C26—C25—H25	120.8
N17—C15—C16	119.27 (14)	C25—C26—C21	120.58 (16)
C11—C16—C15	119.22 (14)	C25—C26—H26	119.7
C11—C16—H16	120.4	C21—C26—H26	119.7
C15—C16—H16	120.4
C10—N1—C2—C3	−3.3 (2)	C2—C11—C12—C13	−174.10 (15)
C10—N1—C2—C11	174.81 (14)	C11—C12—C13—N14	0.3 (3)
N1—C2—C3—N4	5.3 (2)	C12—C13—N14—C15	−1.1 (3)
C11—C2—C3—N4	−172.55 (14)	C13—N14—C15—N17	179.56 (15)
N1—C2—C3—C21	−173.81 (14)	C13—N14—C15—C16	1.1 (2)
C11—C2—C3—C21	8.3 (2)	C12—C11—C16—C15	−0.5 (2)
C2—C3—N4—C5	−2.1 (2)	C2—C11—C16—C15	174.11 (14)
C21—C3—N4—C5	177.08 (13)	N14—C15—C16—C11	−0.4 (2)
C3—N4—C5—N6	177.84 (14)	N17—C15—C16—C11	−178.81 (15)
C3—N4—C5—C10	−2.6 (2)	N14—C15—N17—C18	−3.3 (2)
N4—C5—N6—C7	178.44 (16)	C16—C15—N17—C18	175.18 (15)
C10—C5—N6—C7	−1.1 (2)	C15—N17—C18—C20	−75.1 (2)
C5—N6—C7—C8	−0.9 (3)	C15—N17—C18—C19	162.02 (17)
N6—C7—C8—C9	1.8 (3)	N4—C3—C21—C26	−143.17 (15)
C7—C8—C9—C10	−0.7 (3)	C2—C3—C21—C26	36.0 (2)
C2—N1—C10—C5	−1.5 (2)	N4—C3—C21—C22	32.6 (2)
C2—N1—C10—C9	−179.42 (16)	C2—C3—C21—C22	−148.19 (15)
N4—C5—C10—N1	4.7 (2)	C26—C21—C22—C23	−2.3 (2)
N6—C5—C10—N1	−175.85 (15)	C3—C21—C22—C23	−178.29 (15)
N4—C5—C10—C9	−177.38 (16)	C21—C22—C23—C24	1.4 (3)
N6—C5—C10—C9	2.1 (3)	C22—C23—C24—F1	−179.53 (16)
C8—C9—C10—N1	176.83 (18)	C22—C23—C24—C25	0.6 (3)
C8—C9—C10—C5	−1.1 (3)	F1—C24—C25—C26	178.49 (16)
N1—C2—C11—C16	−128.17 (16)	C23—C24—C25—C26	−1.7 (3)
C3—C2—C11—C16	49.8 (2)	C24—C25—C26—C21	0.7 (3)
N1—C2—C11—C12	46.3 (2)	C22—C21—C26—C25	1.2 (2)
C3—C2—C11—C12	−135.71 (16)	C3—C21—C26—C25	177.00 (15)
C16—C11—C12—C13	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N6i	0.91	2.32	3.166 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N17—H17⋯N6i	0.91	2.32	3.166 (2)	154

Symmetry code: (i) .