2-(4-Fluoro-phen-yl)-3-(4-pyrid-yl)pyrido[2,3-b]pyrazine.

In the crystal structure of the title compound, C(18)H(11)FN(4), the pyridopyrazine system makes dihedral angles of 45.51 (7) and 44.75 (7)° with the attached 4-fluoro-phenyl ring and the pyridine ring, respectively. The 4-fluoro-phenyl ring makes a dihedral angle of 54.54 (8)° with the pyridine ring. The pyridine ring part of the pyridopyrazine ring and the pyrazine ring of two c-glide-plane-related mol-ecules form π-π inter-actions. The angle between the planes is 2.09 (7)° and the distance between the centroids is 3.557 (1)Å.

Related literature

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

Experimental

Crystal data

C18H11FN4

M = 302.31

Monoclinic,

a = 17.222 (9) Å

b = 11.2199 (12) Å

c = 7.329 (4) Å

β = 91.80 (3)°

V = 1415.4 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.80 mm−1

T = 193 K

0.64 × 0.51 × 0.06 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: numerical (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.675, T max = 0.949

2766 measured reflections

2677 independent reflections

2309 reflections with I > 2σ(I)

R int = 0.029

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

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.07

2677 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 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/S1600536809037295/nc2158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037295/nc2158Isup2.hkl

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

C18H11FN4	F(000) = 624
Mr = 302.31	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.222 (9) Å	θ = 35–50°
b = 11.2199 (12) Å	µ = 0.80 mm−1
c = 7.329 (4) Å	T = 193 K
β = 91.80 (3)°	Plate, yellow
V = 1415.4 (10) Å3	0.64 × 0.51 × 0.06 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2309 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.029
graphite	θmax = 70.1°, θmin = 2.6°
ω/2θ scans	h = 0→20
Absorption correction: numerical (CORINC; Dräger & Gattow, 1971)	k = 0→13
Tmin = 0.675, Tmax = 0.949	l = −8→8
2766 measured reflections	3 standard reflections every 60 min
2677 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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0797P)2 + 0.3717P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2677 reflections	Δρmax = 0.22 e Å−3
209 parameters	Δρmin = −0.24 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: 0.0012 (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
C1	0.30818 (9)	0.56244 (13)	0.5692 (2)	0.0294 (4)
N2	0.37936 (8)	0.58947 (12)	0.62301 (19)	0.0323 (3)
C3	0.39843 (9)	0.70720 (14)	0.6323 (2)	0.0317 (4)
N4	0.47243 (8)	0.73360 (13)	0.6904 (2)	0.0386 (4)
C5	0.48914 (10)	0.84780 (17)	0.7036 (2)	0.0419 (4)
H5	0.5405	0.8683	0.7432	0.050*
C6	0.43761 (11)	0.94200 (16)	0.6641 (2)	0.0409 (4)
H6	0.4539	1.0223	0.6795	0.049*
C7	0.36428 (10)	0.91673 (14)	0.6039 (2)	0.0362 (4)
H7	0.3283	0.9786	0.5750	0.043*
C8	0.34280 (9)	0.79530 (14)	0.5851 (2)	0.0307 (4)
N9	0.27022 (8)	0.76613 (11)	0.52296 (18)	0.0312 (3)
C10	0.25245 (9)	0.65216 (13)	0.5120 (2)	0.0291 (3)
C11	0.28858 (9)	0.43306 (14)	0.5734 (2)	0.0315 (4)
C12	0.22105 (10)	0.39077 (15)	0.6474 (2)	0.0386 (4)
H12	0.1837	0.4445	0.6930	0.046*
C13	0.20869 (11)	0.26876 (16)	0.6541 (3)	0.0420 (4)
H13	0.1619	0.2412	0.7048	0.050*
N14	0.25842 (9)	0.18762 (13)	0.5938 (2)	0.0435 (4)
C15	0.32369 (11)	0.22990 (15)	0.5235 (2)	0.0402 (4)
H15	0.3602	0.1741	0.4801	0.048*
C16	0.34126 (10)	0.34977 (14)	0.5101 (2)	0.0344 (4)
H16	0.3885	0.3749	0.4585	0.041*
C17	0.17368 (9)	0.62393 (13)	0.4370 (2)	0.0293 (3)
C18	0.16111 (9)	0.53902 (13)	0.3005 (2)	0.0333 (4)
H18	0.2036	0.4945	0.2571	0.040*
C19	0.08724 (10)	0.51921 (15)	0.2280 (3)	0.0398 (4)
H19	0.0786	0.4614	0.1348	0.048*
C20	0.02664 (10)	0.58435 (16)	0.2928 (3)	0.0410 (4)
C21	0.03648 (10)	0.66822 (17)	0.4283 (3)	0.0446 (4)
H21	−0.0066	0.7112	0.4724	0.054*
C22	0.11058 (10)	0.68841 (15)	0.4987 (2)	0.0379 (4)
H22	0.1187	0.7472	0.5906	0.046*
F23	−0.04531 (7)	0.56622 (13)	0.21986 (18)	0.0642 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0316 (8)	0.0300 (8)	0.0268 (8)	0.0022 (6)	0.0028 (6)	0.0011 (6)
N2	0.0312 (7)	0.0329 (7)	0.0329 (7)	0.0013 (5)	0.0011 (5)	0.0018 (5)
C3	0.0319 (8)	0.0350 (8)	0.0283 (8)	−0.0016 (6)	0.0036 (6)	−0.0013 (6)
N4	0.0326 (7)	0.0447 (8)	0.0384 (8)	−0.0024 (6)	−0.0008 (6)	−0.0001 (6)
C5	0.0346 (9)	0.0514 (10)	0.0397 (10)	−0.0121 (7)	0.0005 (7)	−0.0046 (8)
C6	0.0436 (10)	0.0399 (9)	0.0396 (10)	−0.0126 (7)	0.0097 (8)	−0.0075 (7)
C7	0.0384 (9)	0.0304 (8)	0.0403 (10)	−0.0025 (6)	0.0081 (7)	−0.0029 (7)
C8	0.0312 (8)	0.0312 (8)	0.0299 (8)	−0.0019 (6)	0.0055 (6)	−0.0026 (6)
N9	0.0317 (7)	0.0280 (7)	0.0342 (7)	0.0007 (5)	0.0031 (5)	−0.0007 (5)
C10	0.0311 (8)	0.0279 (7)	0.0284 (8)	0.0009 (6)	0.0040 (6)	0.0000 (6)
C11	0.0338 (8)	0.0305 (8)	0.0298 (8)	0.0012 (6)	−0.0030 (6)	0.0046 (6)
C12	0.0367 (9)	0.0374 (9)	0.0418 (10)	0.0034 (7)	0.0020 (7)	0.0084 (7)
C13	0.0401 (9)	0.0421 (9)	0.0435 (10)	−0.0070 (7)	−0.0002 (7)	0.0115 (8)
N14	0.0523 (9)	0.0337 (7)	0.0443 (9)	−0.0024 (6)	−0.0008 (7)	0.0060 (6)
C15	0.0499 (10)	0.0308 (8)	0.0399 (10)	0.0044 (7)	0.0016 (8)	0.0018 (7)
C16	0.0366 (8)	0.0330 (8)	0.0334 (9)	0.0014 (6)	−0.0008 (6)	0.0029 (6)
C17	0.0312 (8)	0.0257 (7)	0.0311 (8)	0.0005 (6)	0.0016 (6)	0.0029 (6)
C18	0.0365 (8)	0.0282 (7)	0.0352 (9)	0.0005 (6)	0.0013 (7)	0.0009 (6)
C19	0.0453 (10)	0.0345 (8)	0.0394 (10)	−0.0070 (7)	−0.0033 (7)	−0.0014 (7)
C20	0.0295 (8)	0.0503 (10)	0.0431 (10)	−0.0074 (7)	−0.0027 (7)	0.0052 (8)
C21	0.0329 (9)	0.0533 (10)	0.0480 (11)	0.0059 (7)	0.0050 (8)	−0.0022 (8)
C22	0.0358 (9)	0.0388 (9)	0.0393 (10)	0.0027 (7)	0.0016 (7)	−0.0060 (7)
F23	0.0348 (6)	0.0915 (10)	0.0656 (8)	−0.0096 (6)	−0.0107 (5)	−0.0054 (7)

C1—N2	1.311 (2)	C12—H12	0.9500
C1—C10	1.444 (2)	C13—N14	1.335 (2)
C1—C11	1.491 (2)	C13—H13	0.9500
N2—C3	1.362 (2)	N14—C15	1.338 (2)
C3—N4	1.363 (2)	C15—C16	1.383 (2)
C3—C8	1.412 (2)	C15—H15	0.9500
N4—C5	1.316 (2)	C16—H16	0.9500
C5—C6	1.404 (3)	C17—C22	1.393 (2)
C5—H5	0.9500	C17—C18	1.393 (2)
C6—C7	1.355 (3)	C18—C19	1.381 (2)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.417 (2)	C19—C20	1.371 (3)
C7—H7	0.9500	C19—H19	0.9500
C8—N9	1.357 (2)	C20—F23	1.349 (2)
N9—C10	1.3167 (19)	C20—C21	1.375 (3)
C10—C17	1.482 (2)	C21—C22	1.380 (2)
C11—C12	1.383 (2)	C21—H21	0.9500
C11—C16	1.392 (2)	C22—H22	0.9500
C12—C13	1.386 (2)
N2—C1—C10	122.18 (14)	C13—C12—H12	120.5
N2—C1—C11	115.41 (13)	N14—C13—C12	124.13 (17)
C10—C1—C11	122.41 (14)	N14—C13—H13	117.9
C1—N2—C3	117.45 (14)	C12—C13—H13	117.9
N2—C3—N4	116.60 (14)	C13—N14—C15	116.18 (15)
N2—C3—C8	120.38 (15)	N14—C15—C16	124.10 (17)
N4—C3—C8	123.01 (15)	N14—C15—H15	118.0
C5—N4—C3	115.75 (15)	C16—C15—H15	118.0
N4—C5—C6	125.61 (16)	C15—C16—C11	118.86 (16)
N4—C5—H5	117.2	C15—C16—H16	120.6
C6—C5—H5	117.2	C11—C16—H16	120.6
C7—C6—C5	119.09 (16)	C22—C17—C18	118.88 (15)
C7—C6—H6	120.5	C22—C17—C10	118.89 (14)
C5—C6—H6	120.5	C18—C17—C10	122.15 (14)
C6—C7—C8	118.08 (16)	C19—C18—C17	120.45 (16)
C6—C7—H7	121.0	C19—C18—H18	119.8
C8—C7—H7	121.0	C17—C18—H18	119.8
N9—C8—C3	121.61 (14)	C20—C19—C18	118.86 (16)
N9—C8—C7	119.96 (14)	C20—C19—H19	120.6
C3—C8—C7	118.43 (15)	C18—C19—H19	120.6
C10—N9—C8	117.69 (13)	F23—C20—C19	118.82 (17)
N9—C10—C1	120.54 (14)	F23—C20—C21	118.69 (17)
N9—C10—C17	116.01 (13)	C19—C20—C21	122.49 (16)
C1—C10—C17	123.44 (13)	C20—C21—C22	118.28 (17)
C12—C11—C16	117.74 (15)	C20—C21—H21	120.9
C12—C11—C1	122.42 (15)	C22—C21—H21	120.9
C16—C11—C1	119.75 (15)	C21—C22—C17	121.02 (16)
C11—C12—C13	118.99 (16)	C21—C22—H22	119.5
C11—C12—H12	120.5	C17—C22—H22	119.5
C10—C1—N2—C3	3.3 (2)	N2—C1—C11—C16	−43.4 (2)
C11—C1—N2—C3	−176.00 (14)	C10—C1—C11—C16	137.36 (16)
C1—N2—C3—N4	179.30 (14)	C16—C11—C12—C13	−0.4 (2)
C1—N2—C3—C8	0.0 (2)	C1—C11—C12—C13	−176.96 (16)
N2—C3—N4—C5	−178.11 (15)	C11—C12—C13—N14	0.3 (3)
C8—C3—N4—C5	1.2 (2)	C12—C13—N14—C15	0.0 (3)
C3—N4—C5—C6	0.3 (3)	C13—N14—C15—C16	−0.3 (3)
N4—C5—C6—C7	−1.3 (3)	N14—C15—C16—C11	0.2 (3)
C5—C6—C7—C8	0.6 (3)	C12—C11—C16—C15	0.2 (2)
N2—C3—C8—N9	−2.6 (2)	C1—C11—C16—C15	176.82 (15)
N4—C3—C8—N9	178.18 (15)	N9—C10—C17—C22	−45.2 (2)
N2—C3—C8—C7	177.49 (15)	C1—C10—C17—C22	135.38 (17)
N4—C3—C8—C7	−1.8 (2)	N9—C10—C17—C18	131.58 (16)
C6—C7—C8—N9	−179.16 (15)	C1—C10—C17—C18	−47.8 (2)
C6—C7—C8—C3	0.8 (2)	C22—C17—C18—C19	−0.1 (2)
C3—C8—N9—C10	1.6 (2)	C10—C17—C18—C19	−176.90 (15)
C7—C8—N9—C10	−178.43 (15)	C17—C18—C19—C20	−0.1 (2)
C8—N9—C10—C1	1.6 (2)	C18—C19—C20—F23	179.01 (16)
C8—N9—C10—C17	−177.79 (13)	C18—C19—C20—C21	−0.5 (3)
N2—C1—C10—N9	−4.3 (2)	F23—C20—C21—C22	−178.31 (17)
C11—C1—C10—N9	174.95 (15)	C19—C20—C21—C22	1.2 (3)
N2—C1—C10—C17	175.07 (14)	C20—C21—C22—C17	−1.3 (3)
C11—C1—C10—C17	−5.7 (2)	C18—C17—C22—C21	0.8 (3)
N2—C1—C11—C12	133.14 (17)	C10—C17—C22—C21	177.73 (16)
C10—C1—C11—C12	−46.1 (2)