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

In the crystal structure of the title compound, C(18)H(11)FN(4), the pyridopyrazine ring makes dihedral angles of 34.67 (7) and 52.24 (7)° with the 4-fluoro-phenyl and pyridine rings, respectively. The 4-fluoro-phenyl ring makes a dihedral angle of 59.56 (9)° with the pyridine ring.

Related literature

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

Experimental

Crystal data

C18H11FN4

M = 302.31

Monoclinic,

a = 9.7163 (9) Å

b = 13.7937 (6) Å

c = 10.8164 (10) Å

β = 90.994 (5)°

V = 1449.4 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.78 mm−1

T = 193 K

0.30 × 0.25 × 0.22 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2906 measured reflections

2753 independent reflections

2654 reflections with I > 2σ(I)

R int = 0.023

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

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.149

S = 1.20

2753 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.31 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/S1600536809037970/bt5066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037970/bt5066Isup2.hkl

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

C18H11FN4	F(000) = 624
Mr = 302.31	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.7163 (9) Å	θ = 65–69°
b = 13.7937 (6) Å	µ = 0.78 mm−1
c = 10.8164 (10) Å	T = 193 K
β = 90.994 (5)°	Block, colourless
V = 1449.4 (2) Å3	0.30 × 0.25 × 0.22 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.023
Radiation source: rotating anode	θmax = 70.0°, θmin = 4.6°
graphite	h = −11→11
ω/2θ scans	k = 0→16
2906 measured reflections	l = 0→13
2753 independent reflections	3 standard reflections every 60 min
2654 reflections with I > 2σ(I)	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) = 0.149	w = 1/[σ2(Fo2) + (0.073P)2 + 0.6448P] where P = (Fo2 + 2Fc2)/3
S = 1.20	(Δ/σ)max < 0.001
2753 reflections	Δρmax = 0.31 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: 0.0079 (9)

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	0.71724 (16)	0.38396 (12)	0.46833 (15)	0.0271 (4)
N2	0.82823 (14)	0.41887 (10)	0.52355 (13)	0.0300 (4)
C3	0.81675 (18)	0.44950 (12)	0.64285 (16)	0.0294 (4)
C4	0.9322 (2)	0.48632 (15)	0.70813 (17)	0.0383 (4)
H4	1.0203	0.4880	0.6715	0.046*
C5	0.9135 (2)	0.51935 (15)	0.82524 (18)	0.0430 (5)
H5	0.9892	0.5436	0.8727	0.052*
C6	0.7806 (2)	0.51712 (15)	0.87511 (18)	0.0422 (5)
H6	0.7698	0.5425	0.9560	0.051*
N7	0.67047 (17)	0.48270 (12)	0.81831 (14)	0.0385 (4)
C8	0.68851 (18)	0.44723 (12)	0.70263 (15)	0.0289 (4)
N9	0.57616 (14)	0.40774 (11)	0.64607 (13)	0.0297 (4)
C10	0.58915 (16)	0.37376 (11)	0.53266 (15)	0.0263 (4)
C11	0.73166 (16)	0.36165 (12)	0.33454 (15)	0.0277 (4)
C12	0.64457 (18)	0.40275 (13)	0.24579 (16)	0.0324 (4)
H12	0.5701	0.4429	0.2695	0.039*
C13	0.6681 (2)	0.38414 (14)	0.12271 (17)	0.0377 (4)
H13	0.6082	0.4129	0.0629	0.045*
N14	0.77022 (17)	0.32808 (12)	0.08247 (15)	0.0406 (4)
C15	0.85276 (19)	0.28932 (14)	0.16925 (18)	0.0370 (4)
H15	0.9263	0.2494	0.1428	0.044*
C16	0.83866 (17)	0.30326 (13)	0.29441 (17)	0.0322 (4)
H16	0.9005	0.2737	0.3520	0.039*
C17	0.46722 (16)	0.32309 (12)	0.47894 (15)	0.0270 (4)
C18	0.48092 (17)	0.24153 (13)	0.40375 (16)	0.0307 (4)
H18	0.5702	0.2194	0.3830	0.037*
C19	0.36587 (19)	0.19234 (14)	0.35891 (18)	0.0363 (4)
H19	0.3750	0.1363	0.3086	0.044*
C20	0.23859 (18)	0.22707 (15)	0.3895 (2)	0.0405 (5)
C21	0.21958 (18)	0.30696 (14)	0.4637 (2)	0.0404 (5)
H21	0.1298	0.3289	0.4831	0.049*
C22	0.33549 (17)	0.35415 (13)	0.50905 (17)	0.0329 (4)
H22	0.3251	0.4087	0.5617	0.039*
F23	0.12564 (12)	0.17883 (11)	0.34584 (16)	0.0658 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0255 (8)	0.0238 (8)	0.0320 (9)	0.0011 (6)	−0.0009 (6)	0.0019 (6)
N2	0.0273 (7)	0.0305 (7)	0.0322 (7)	−0.0026 (6)	0.0003 (6)	0.0008 (6)
C3	0.0308 (9)	0.0265 (8)	0.0307 (8)	−0.0022 (6)	−0.0022 (7)	0.0029 (6)
C4	0.0338 (9)	0.0418 (10)	0.0390 (10)	−0.0094 (8)	−0.0035 (7)	0.0022 (8)
C5	0.0460 (11)	0.0450 (11)	0.0375 (10)	−0.0158 (9)	−0.0105 (8)	0.0024 (8)
C6	0.0540 (12)	0.0420 (11)	0.0304 (9)	−0.0102 (9)	−0.0038 (8)	−0.0039 (8)
N7	0.0420 (9)	0.0417 (9)	0.0320 (8)	−0.0044 (7)	0.0009 (6)	−0.0040 (6)
C8	0.0314 (8)	0.0258 (8)	0.0295 (8)	−0.0006 (6)	−0.0011 (6)	0.0018 (6)
N9	0.0283 (7)	0.0307 (8)	0.0303 (7)	−0.0004 (6)	0.0007 (5)	−0.0001 (6)
C10	0.0263 (8)	0.0236 (8)	0.0290 (8)	0.0019 (6)	−0.0001 (6)	0.0008 (6)
C11	0.0243 (8)	0.0273 (8)	0.0315 (9)	−0.0045 (6)	0.0026 (6)	−0.0010 (6)
C12	0.0319 (9)	0.0315 (9)	0.0338 (9)	0.0008 (7)	0.0023 (7)	0.0009 (7)
C13	0.0413 (10)	0.0387 (10)	0.0329 (9)	−0.0040 (8)	−0.0023 (7)	0.0012 (7)
N14	0.0454 (9)	0.0425 (9)	0.0341 (8)	−0.0067 (7)	0.0062 (7)	−0.0070 (7)
C15	0.0324 (9)	0.0349 (9)	0.0441 (10)	−0.0043 (7)	0.0090 (8)	−0.0096 (8)
C16	0.0254 (8)	0.0327 (9)	0.0384 (9)	−0.0022 (7)	0.0012 (7)	−0.0041 (7)
C17	0.0246 (8)	0.0279 (8)	0.0283 (8)	−0.0010 (6)	0.0000 (6)	0.0035 (6)
C18	0.0251 (8)	0.0315 (9)	0.0356 (9)	−0.0002 (7)	0.0010 (6)	−0.0007 (7)
C19	0.0341 (9)	0.0330 (9)	0.0418 (10)	−0.0029 (7)	−0.0028 (7)	−0.0063 (7)
C20	0.0263 (9)	0.0387 (10)	0.0561 (12)	−0.0063 (7)	−0.0085 (8)	−0.0023 (9)
C21	0.0235 (9)	0.0386 (10)	0.0593 (12)	0.0021 (7)	0.0004 (8)	−0.0008 (9)
C22	0.0285 (9)	0.0295 (9)	0.0407 (9)	0.0020 (7)	0.0024 (7)	−0.0014 (7)
F23	0.0305 (6)	0.0594 (9)	0.1070 (12)	−0.0084 (6)	−0.0157 (7)	−0.0256 (8)

C1—N2	1.315 (2)	C12—H12	0.9500
C1—C10	1.443 (2)	C13—N14	1.336 (3)
C1—C11	1.488 (2)	C13—H13	0.9500
N2—C3	1.364 (2)	N14—C15	1.336 (3)
C3—C4	1.410 (2)	C15—C16	1.377 (3)
C3—C8	1.414 (2)	C15—H15	0.9500
C4—C5	1.361 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—C22	1.394 (2)
C5—C6	1.409 (3)	C17—C18	1.396 (2)
C5—H5	0.9500	C18—C19	1.388 (2)
C6—N7	1.313 (2)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.372 (3)
N7—C8	1.358 (2)	C19—H19	0.9500
C8—N9	1.356 (2)	C20—F23	1.361 (2)
N9—C10	1.321 (2)	C20—C21	1.378 (3)
C10—C17	1.485 (2)	C21—C22	1.383 (3)
C11—C12	1.389 (2)	C21—H21	0.9500
C11—C16	1.391 (2)	C22—H22	0.9500
C12—C13	1.379 (3)
N2—C1—C10	121.60 (15)	C11—C12—H12	120.6
N2—C1—C11	115.28 (14)	N14—C13—C12	123.97 (18)
C10—C1—C11	123.03 (14)	N14—C13—H13	118.0
C1—N2—C3	117.59 (14)	C12—C13—H13	118.0
N2—C3—C4	120.53 (16)	C15—N14—C13	116.28 (16)
N2—C3—C8	120.86 (15)	N14—C15—C16	124.50 (17)
C4—C3—C8	118.60 (16)	N14—C15—H15	117.7
C5—C4—C3	117.99 (17)	C16—C15—H15	117.7
C5—C4—H4	121.0	C15—C16—C11	118.40 (17)
C3—C4—H4	121.0	C15—C16—H16	120.8
C4—C5—C6	119.12 (17)	C11—C16—H16	120.8
C4—C5—H5	120.4	C22—C17—C18	118.76 (15)
C6—C5—H5	120.4	C22—C17—C10	119.57 (15)
N7—C6—C5	125.01 (18)	C18—C17—C10	121.58 (15)
N7—C6—H6	117.5	C19—C18—C17	120.87 (16)
C5—C6—H6	117.5	C19—C18—H18	119.6
C6—N7—C8	116.37 (16)	C17—C18—H18	119.6
N9—C8—N7	116.40 (15)	C20—C19—C18	117.97 (17)
N9—C8—C3	120.75 (15)	C20—C19—H19	121.0
N7—C8—C3	122.84 (16)	C18—C19—H19	121.0
C10—N9—C8	118.18 (14)	F23—C20—C19	118.07 (18)
N9—C10—C1	120.67 (15)	F23—C20—C21	118.54 (17)
N9—C10—C17	116.22 (14)	C19—C20—C21	123.38 (17)
C1—C10—C17	123.09 (14)	C20—C21—C22	117.80 (17)
C12—C11—C16	118.06 (16)	C20—C21—H21	121.1
C12—C11—C1	121.39 (15)	C22—C21—H21	121.1
C16—C11—C1	120.45 (15)	C21—C22—C17	121.19 (17)
C13—C12—C11	118.80 (17)	C21—C22—H22	119.4
C13—C12—H12	120.6	C17—C22—H22	119.4
C10—C1—N2—C3	−2.9 (2)	N2—C1—C11—C16	52.5 (2)
C11—C1—N2—C3	173.66 (14)	C10—C1—C11—C16	−130.92 (17)
C1—N2—C3—C4	179.03 (16)	C16—C11—C12—C13	−0.2 (2)
C1—N2—C3—C8	−2.5 (2)	C1—C11—C12—C13	176.03 (16)
N2—C3—C4—C5	177.47 (17)	C11—C12—C13—N14	0.3 (3)
C8—C3—C4—C5	−1.0 (3)	C12—C13—N14—C15	−0.3 (3)
C3—C4—C5—C6	−1.2 (3)	C13—N14—C15—C16	0.2 (3)
C4—C5—C6—N7	1.9 (3)	N14—C15—C16—C11	−0.1 (3)
C5—C6—N7—C8	−0.2 (3)	C12—C11—C16—C15	0.1 (2)
C6—N7—C8—N9	177.15 (16)	C1—C11—C16—C15	−176.17 (15)
C6—N7—C8—C3	−2.2 (3)	N9—C10—C17—C22	34.0 (2)
N2—C3—C8—N9	5.1 (2)	C1—C10—C17—C22	−147.77 (17)
C4—C3—C8—N9	−176.46 (16)	N9—C10—C17—C18	−142.59 (16)
N2—C3—C8—N7	−175.65 (16)	C1—C10—C17—C18	35.6 (2)
C4—C3—C8—N7	2.8 (3)	C22—C17—C18—C19	0.4 (3)
N7—C8—N9—C10	179.00 (15)	C10—C17—C18—C19	177.00 (16)
C3—C8—N9—C10	−1.7 (2)	C17—C18—C19—C20	0.8 (3)
C8—N9—C10—C1	−3.8 (2)	C18—C19—C20—F23	−179.86 (17)
C8—N9—C10—C17	174.53 (14)	C18—C19—C20—C21	−1.1 (3)
N2—C1—C10—N9	6.4 (2)	F23—C20—C21—C22	178.90 (18)
C11—C1—C10—N9	−169.95 (15)	C19—C20—C21—C22	0.1 (3)
N2—C1—C10—C17	−171.78 (15)	C20—C21—C22—C17	1.1 (3)
C11—C1—C10—C17	11.9 (2)	C18—C17—C22—C21	−1.4 (3)
N2—C1—C11—C12	−123.57 (17)	C10—C17—C22—C21	−178.07 (16)
C10—C1—C11—C12	53.0 (2)