N-{4-[3-(4-Fluoro­phen­yl)pyrido[2,3-b]pyrazin-2-yl]-2-pyrid­yl}isopropyl­amine

Koch, P.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536809038173

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2557

doi:10.1107/S1600536809038173

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N-{4-[3-(4-Fluorophenyl)pyrido[2,3-b]pyrazin-2-yl]-2-pyridyl}isopropylamine

Pierre Koch,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^aInstitute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Eberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 10 September 2009; accepted 21 September 2009; online 26 September 2009)

In the crystal structure of the title compound, C₂₁H₁₈FN₅, the pyridopyrazine ring system forms dihedral angles of 33.27 (7) and 48.69 (9)° with the 4-fluorophenyl and pyridine ring, respectively. The dihedral angle of the 4-fluorophenyl and pyridine rings is 57.45 (8)°. The crystal packing is characterized by an intermolecular 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_r = 359.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.127
S = 1.05
3468 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound, {4-[3-(4-fluorophenyl)-pyrido[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-isopropylamine (I), was prepared in the course of our studies on pyridin-4-yl-substituted pyridopyrazines as p38 mitogen-activated protein (MAP) kinase inhibitors.

The microwave-assisted reaction of 1-(4-fluorophenyl)-2-(2-(isopropylamino)-pyridin-4-yl)ethane-1,2-dione and 2,3-diaminopyridine yields two regioisomers, {4-[3-(4-fluorophenyl)-pyrido[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-isopropylamine (I) and {4-[2-(4-fluorophenyl)-pyrido[3,2-b]pyrazin-3-yl]-pyridin-2-yl}-isopropylamine (II). The isomers were separated by flash-chromatography. To identify the two regioisomers X-ray crystallography was used. Herein we present the X-ray crystallographic data of the first eluted isomer I.

As might be expected the 4-fluorophenyl, the pyridine ring as well as the pyridopyrazine ring are planar (Figure 1). The pyridopyrazine ring encloses dihedral angles of 33.27 (7)° and 48.69 (9)° to the 4-fluorophenyl ring and the pyridine ring, respectively. The dihedral angle of the 4-fluorophenyl ring and the pyridine ring measures to 57.45 (8)° to the pyridine ring. The crystal packing is characterized by an intermolecular hydrogen bond N17–H17···N6 2.32 Å.

Related literature top

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

Experimental top

1-(4-Fluorophenyl)-2-(2-(isopropylamino)pyridin-4-yl)ethane-1,2-dione (115 mg, 0.4 mmol), 2,3-diaminopyridine (44 mg, 0.4 mmol), and methanol/glacial acetic acid (3 ml, 9:1, v:v) were combined in a reaction vial. The reaction vessel was heated in a microwave reactor for 5 min at 433 K (initial power 250 W). Then a stream of compressed air cooled the reaction vessel to r.t. The solvent was removed under reduced pressure and the residue was purified by flash-chromatography (silica gel, light petroleum /ethyl acetate 1:1 to 1:4) to yield 46 mg (33%) of I as a yellow solid. Suitable crystals of compound I for X-ray diffraction were obtained from a solution in n-hexane - diethyl ether (2:1) by slow evaporation of the solvent at 298 K.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Spek, 2009).

Figures top

Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level.

N-{4-[3-(4-Fluorophenyl)pyrido[2,3-b]pyrazin-2-yl]- 2-pyridyl}isopropylamine top

Crystal data top

C₂₁H₁₈FN₅	F(000) = 752
M_r = 359.40	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.065P)² + 0.5513P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3468 reflections	Δρ_max = 0.29 e Å⁻³
247 parameters	Δρ_min = −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)

Crystal data top

C₂₁H₁₈FN₅	V = 1823.8 (3) Å³
M_r = 359.40	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.042 (1) Å	µ = 0.72 mm⁻¹
b = 7.6586 (2) Å	T = 193 K
c = 20.095 (2) Å	0.50 × 0.20 × 0.10 mm
β = 100.215 (5)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2912 reflections with I > 2σ(I)
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	R_int = 0.063
T_min = 0.743, T_max = 0.998	3 standard reflections every 60 min
3578 measured reflections	intensity decay: 2%
3468 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
3468 reflections	Δρ_min = −0.28 e Å⁻³
247 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈FN₅
M_r	359.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	12.042 (1), 7.6586 (2), 20.095 (2)
β (°)	100.215 (5)
V (Å³)	1823.8 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.50 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (CORINC; Dräger & Gattow, 1971)
T_min, T_max	0.743, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	3578, 3468, 2912
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.127, 1.05
No. of reflections	3468
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, Z., Wisnoski, D. D., Wolkenberg, S. E., Leister, W. H., Wang, Y. & Lindsley, C. W. (2004). Tetrahedron Lett. 45, 4873–4876. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 10| October 2009| Page o2557

doi:10.1107/S1600536809038173

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-{4-[3-(4-Fluoro­phen­yl)pyrido[2,3-b]pyrazin-2-yl]-2-pyrid­yl}iso­propyl­amine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N-{4-[3-(4-Fluorophenyl)pyrido[2,3-b]pyrazin-2-yl]-2-pyridyl}isopropylamine