4-[3-(4-Fluoro-phen-yl)quinoxalin-2-yl]-N-isopropyl-pyridin-2-amine.

In the crystal structure of the title compound, C(22)H(19)FN(4), the quinoxaline system makes dihedral angles of 32.07 (13) and 69.64 (13)° with the 4-fluoro-phenyl and pyridine rings, respectively. The 4-fluoro-phenyl ring makes a dihedral angle of 71.77 (16)° with the pyridine ring. The crystal structure is stabilized by inter-molecular N-H⋯N hydrogen bonding.

Related literature

For chinoxaline derivatives and their biological activity, see: He et al. (2003 ▶); Kim et al. (2004 ▶).

Experimental

Crystal data

C22H19FN4

M = 358.41

Monoclinic,

a = 17.230 (9) Å

b = 5.386 (3) Å

c = 19.123 (10) Å

β = 96.114 (13)°

V = 1764.4 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.4 × 0.06 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

20392 measured reflections

4217 independent reflections

1201 reflections with I > 2σ(I)

R int = 0.236

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.123

S = 0.74

4217 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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/S1600536809018285/bt2957sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018285/bt2957Isup2.hkl

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

C22H19FN4	F(000) = 752
Mr = 358.41	Dx = 1.349 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 934 reflections
a = 17.230 (9) Å	θ = 2.2–19.5°
b = 5.386 (3) Å	µ = 0.09 mm−1
c = 19.123 (10) Å	T = 173 K
β = 96.114 (13)°	Needle, colourless
V = 1764.4 (16) Å3	0.4 × 0.06 × 0.03 mm
Z = 4

Bruker SMART CCD diffractometer	1201 reflections with I > 2σ(I)
Radiation source: sealed Tube	Rint = 0.236
graphite	θmax = 28.0°, θmin = 1.5°
CCD scans	h = −22→21
20392 measured reflections	k = −7→6
4217 independent reflections	l = −25→25

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-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3
S = 0.74	(Δ/σ)max < 0.001
4217 reflections	Δρmax = 0.23 e Å−3
247 parameters	Δρmin = −0.22 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: 0.0111 (10)

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	0.32320 (13)	−0.2743 (4)	0.12436 (11)	0.0534 (7)
N1	0.64239 (16)	0.7424 (5)	0.21100 (13)	0.0280 (7)
C2	0.5913 (2)	0.5582 (6)	0.20994 (17)	0.0247 (9)
C3	0.5637 (2)	0.4311 (6)	0.14642 (17)	0.0247 (9)
N4	0.59317 (17)	0.4791 (5)	0.08672 (14)	0.0286 (8)
C5	0.6482 (2)	0.6633 (6)	0.08760 (18)	0.0261 (9)
C6	0.6806 (2)	0.7247 (7)	0.02532 (18)	0.0354 (9)
H6	0.6676	0.6298	−0.0162	0.043*
C7	0.7308 (2)	0.9216 (7)	0.02466 (19)	0.0391 (10)
H7	0.7523	0.9632	−0.0176	0.047*
C8	0.7511 (2)	1.0634 (7)	0.08587 (19)	0.0360 (10)
H8	0.7853	1.2010	0.0843	0.043*
C9	0.7220 (2)	1.0048 (6)	0.14717 (18)	0.0320 (10)
H9	0.7362	1.0994	0.1885	0.038*
C10	0.6703 (2)	0.8013 (6)	0.14864 (18)	0.0288 (9)
C11	0.5688 (2)	0.4924 (6)	0.28109 (17)	0.0266 (9)
C12	0.5957 (2)	0.2739 (6)	0.31406 (17)	0.0283 (9)
H12	0.6229	0.1531	0.2899	0.034*
C13	0.5814 (2)	0.2386 (6)	0.38249 (17)	0.0299 (9)
H13	0.6023	0.0934	0.4056	0.036*
N14	0.54053 (16)	0.3921 (5)	0.41920 (13)	0.0260 (7)
C15	0.50848 (19)	0.5941 (6)	0.38430 (17)	0.0259 (9)
C16	0.5247 (2)	0.6521 (6)	0.31639 (17)	0.0271 (9)
H16	0.5054	0.8016	0.2946	0.033*
N17	0.46189 (16)	0.7389 (5)	0.42120 (13)	0.0289 (7)
H17	0.4566	0.6623	0.4685	0.035*
C18	0.4038 (2)	0.9131 (6)	0.38765 (17)	0.0309 (9)
H18	0.4304	1.0266	0.3564	0.037*
C19	0.3386 (2)	0.7750 (7)	0.34280 (18)	0.0419 (10)
H19A	0.3128	0.6598	0.3726	0.063*
H19B	0.3609	0.6818	0.3057	0.063*
H19C	0.3004	0.8949	0.3214	0.063*
C20	0.3708 (2)	1.0676 (6)	0.44350 (17)	0.0374 (10)
H20A	0.3427	0.9596	0.4735	0.056*
H20B	0.3347	1.1917	0.4210	0.056*
H20C	0.4134	1.1516	0.4722	0.056*
C21	0.4997 (2)	0.2437 (6)	0.14209 (16)	0.0255 (8)
C22	0.4995 (2)	0.0513 (6)	0.09329 (17)	0.0301 (9)
H22	0.5402	0.0418	0.0636	0.036*
C23	0.4409 (2)	−0.1263 (6)	0.08723 (18)	0.0356 (10)
H23	0.4414	−0.2598	0.0548	0.043*
C24	0.3825 (2)	−0.1020 (7)	0.1296 (2)	0.0360 (10)
C25	0.3785 (2)	0.0856 (7)	0.17772 (18)	0.0347 (10)
H25	0.3365	0.0952	0.2060	0.042*
C26	0.4380 (2)	0.2604 (7)	0.18368 (17)	0.0321 (9)
H26	0.4367	0.3928	0.2164	0.039*

	U11	U22	U33	U12	U13	U23
F1	0.0456 (16)	0.0392 (14)	0.0736 (16)	−0.0154 (12)	−0.0022 (12)	0.0043 (13)
N1	0.0310 (19)	0.0222 (16)	0.0312 (17)	0.0018 (16)	0.0047 (14)	0.0014 (15)
C2	0.025 (2)	0.020 (2)	0.030 (2)	0.0058 (17)	0.0039 (18)	0.0025 (18)
C3	0.027 (2)	0.022 (2)	0.026 (2)	0.0052 (17)	0.0060 (18)	−0.0013 (18)
N4	0.0292 (19)	0.0244 (18)	0.0325 (18)	0.0068 (15)	0.0053 (15)	0.0005 (14)
C5	0.028 (2)	0.024 (2)	0.027 (2)	0.0018 (17)	0.0059 (18)	0.0003 (17)
C6	0.037 (3)	0.033 (2)	0.037 (2)	0.005 (2)	0.0078 (19)	−0.002 (2)
C7	0.038 (3)	0.040 (3)	0.040 (3)	0.007 (2)	0.012 (2)	0.011 (2)
C8	0.031 (3)	0.030 (2)	0.047 (2)	0.0018 (18)	0.005 (2)	0.004 (2)
C9	0.029 (2)	0.029 (2)	0.038 (2)	0.0020 (18)	0.0052 (19)	0.0032 (18)
C10	0.028 (2)	0.027 (2)	0.032 (2)	0.0022 (18)	0.0067 (18)	0.0028 (18)
C11	0.026 (2)	0.025 (2)	0.029 (2)	−0.0075 (17)	0.0027 (18)	−0.0067 (18)
C12	0.033 (2)	0.021 (2)	0.030 (2)	0.0001 (18)	0.0025 (18)	−0.0038 (18)
C13	0.032 (2)	0.020 (2)	0.039 (2)	0.0047 (19)	0.0096 (19)	0.0011 (19)
N14	0.0308 (19)	0.0169 (16)	0.0307 (17)	−0.0021 (15)	0.0051 (15)	−0.0004 (14)
C15	0.026 (2)	0.022 (2)	0.030 (2)	−0.0021 (18)	0.0031 (18)	−0.0024 (18)
C16	0.035 (2)	0.018 (2)	0.028 (2)	−0.0004 (16)	0.0027 (19)	−0.0013 (16)
N17	0.0362 (19)	0.0258 (17)	0.0254 (16)	0.0099 (15)	0.0060 (14)	0.0040 (15)
C18	0.032 (2)	0.025 (2)	0.035 (2)	−0.0007 (19)	0.0040 (19)	−0.0001 (18)
C19	0.037 (3)	0.046 (3)	0.042 (2)	0.001 (2)	0.001 (2)	−0.002 (2)
C20	0.041 (3)	0.029 (2)	0.044 (2)	0.0097 (19)	0.014 (2)	0.0001 (19)
C21	0.029 (2)	0.0200 (19)	0.0268 (19)	0.0030 (19)	0.0021 (17)	0.0039 (18)
C22	0.033 (2)	0.024 (2)	0.033 (2)	0.0069 (18)	0.0013 (19)	0.0042 (19)
C23	0.041 (3)	0.021 (2)	0.043 (2)	0.0047 (19)	−0.006 (2)	−0.0029 (18)
C24	0.035 (3)	0.026 (2)	0.045 (2)	−0.011 (2)	−0.003 (2)	0.009 (2)
C25	0.031 (3)	0.037 (2)	0.035 (2)	0.003 (2)	0.0031 (19)	0.006 (2)
C26	0.031 (2)	0.033 (2)	0.032 (2)	0.001 (2)	0.0004 (18)	−0.0017 (19)

F1—C24	1.376 (4)	C15—N17	1.368 (4)
N1—C2	1.325 (4)	C15—C16	1.393 (4)
N1—C10	1.370 (4)	C16—H16	0.9500
C2—C3	1.431 (4)	N17—C18	1.469 (4)
C2—C11	1.497 (4)	N17—H17	1.0071
C3—N4	1.324 (4)	C18—C20	1.512 (4)
C3—C21	1.491 (4)	C18—C19	1.532 (4)
N4—C5	1.371 (4)	C18—H18	1.0000
C5—C10	1.402 (4)	C19—H19A	0.9800
C5—C6	1.407 (4)	C19—H19B	0.9800
C6—C7	1.370 (5)	C19—H19C	0.9800
C6—H6	0.9500	C20—H20A	0.9800
C7—C8	1.410 (4)	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800
C8—C9	1.360 (4)	C21—C22	1.394 (4)
C8—H8	0.9500	C21—C26	1.397 (4)
C9—C10	1.414 (4)	C22—C23	1.386 (5)
C9—H9	0.9500	C22—H22	0.9500
C11—C16	1.372 (4)	C23—C24	1.363 (4)
C11—C12	1.391 (4)	C23—H23	0.9500
C12—C13	1.370 (4)	C24—C25	1.373 (4)
C12—H12	0.9500	C25—C26	1.387 (4)
C13—N14	1.334 (4)	C25—H25	0.9500
C13—H13	0.9500	C26—H26	0.9500
N14—C15	1.362 (4)
C2—N1—C10	117.0 (3)	C15—C16—H16	120.2
N1—C2—C3	122.1 (3)	C15—N17—C18	123.3 (3)
N1—C2—C11	113.5 (3)	C15—N17—H17	110.1
C3—C2—C11	124.3 (3)	C18—N17—H17	122.1
N4—C3—C2	121.0 (3)	N17—C18—C20	109.5 (3)
N4—C3—C21	115.7 (3)	N17—C18—C19	111.1 (3)
C2—C3—C21	123.2 (3)	C20—C18—C19	110.7 (3)
C3—N4—C5	117.3 (3)	N17—C18—H18	108.5
N4—C5—C10	121.4 (3)	C20—C18—H18	108.5
N4—C5—C6	119.7 (3)	C19—C18—H18	108.5
C10—C5—C6	118.8 (3)	C18—C19—H19A	109.5
C7—C6—C5	119.9 (3)	C18—C19—H19B	109.5
C7—C6—H6	120.1	H19A—C19—H19B	109.5
C5—C6—H6	120.1	C18—C19—H19C	109.5
C6—C7—C8	120.8 (3)	H19A—C19—H19C	109.5
C6—C7—H7	119.6	H19B—C19—H19C	109.5
C8—C7—H7	119.6	C18—C20—H20A	109.5
C9—C8—C7	120.6 (4)	C18—C20—H20B	109.5
C9—C8—H8	119.7	H20A—C20—H20B	109.5
C7—C8—H8	119.7	C18—C20—H20C	109.5
C8—C9—C10	119.2 (4)	H20A—C20—H20C	109.5
C8—C9—H9	120.4	H20B—C20—H20C	109.5
C10—C9—H9	120.4	C22—C21—C26	118.8 (3)
N1—C10—C5	120.8 (3)	C22—C21—C3	119.3 (3)
N1—C10—C9	118.5 (3)	C26—C21—C3	121.9 (3)
C5—C10—C9	120.7 (3)	C23—C22—C21	121.2 (3)
C16—C11—C12	118.8 (3)	C23—C22—H22	119.4
C16—C11—C2	120.6 (3)	C21—C22—H22	119.4
C12—C11—C2	120.4 (3)	C24—C23—C22	117.4 (3)
C13—C12—C11	117.7 (3)	C24—C23—H23	121.3
C13—C12—H12	121.1	C22—C23—H23	121.3
C11—C12—H12	121.1	C23—C24—C25	124.2 (4)
N14—C13—C12	125.1 (3)	C23—C24—F1	118.8 (4)
N14—C13—H13	117.4	C25—C24—F1	117.0 (4)
C12—C13—H13	117.4	C24—C25—C26	117.7 (4)
C13—N14—C15	116.5 (3)	C24—C25—H25	121.1
N14—C15—N17	115.6 (3)	C26—C25—H25	121.1
N14—C15—C16	121.6 (3)	C25—C26—C21	120.6 (4)
N17—C15—C16	122.7 (3)	C25—C26—H26	119.7
C11—C16—C15	119.7 (3)	C21—C26—H26	119.7
C11—C16—H16	120.2
C10—N1—C2—C3	−2.4 (5)	C2—C11—C12—C13	171.9 (3)
C10—N1—C2—C11	175.3 (3)	C11—C12—C13—N14	3.4 (5)
N1—C2—C3—N4	5.8 (5)	C12—C13—N14—C15	2.5 (5)
C11—C2—C3—N4	−171.7 (3)	C13—N14—C15—N17	175.2 (3)
N1—C2—C3—C21	−172.7 (3)	C13—N14—C15—C16	−6.9 (5)
C11—C2—C3—C21	9.9 (5)	C12—C11—C16—C15	0.6 (5)
C2—C3—N4—C5	−3.1 (5)	C2—C11—C16—C15	−176.1 (3)
C21—C3—N4—C5	175.4 (3)	N14—C15—C16—C11	5.5 (5)
C3—N4—C5—C10	−2.2 (5)	N17—C15—C16—C11	−176.8 (3)
C3—N4—C5—C6	−179.0 (3)	N14—C15—N17—C18	−160.1 (3)
N4—C5—C6—C7	174.8 (3)	C16—C15—N17—C18	22.0 (5)
C10—C5—C6—C7	−2.1 (5)	C15—N17—C18—C20	−172.2 (3)
C5—C6—C7—C8	0.4 (5)	C15—N17—C18—C19	65.2 (4)
C6—C7—C8—C9	1.0 (6)	N4—C3—C21—C22	31.4 (5)
C7—C8—C9—C10	−0.7 (5)	C2—C3—C21—C22	−150.1 (3)
C2—N1—C10—C5	−2.9 (5)	N4—C3—C21—C26	−146.0 (3)
C2—N1—C10—C9	177.0 (3)	C2—C3—C21—C26	32.5 (5)
N4—C5—C10—N1	5.5 (5)	C26—C21—C22—C23	−2.2 (5)
C6—C5—C10—N1	−177.7 (3)	C3—C21—C22—C23	−179.7 (3)
N4—C5—C10—C9	−174.4 (3)	C21—C22—C23—C24	1.6 (5)
C6—C5—C10—C9	2.4 (5)	C22—C23—C24—C25	−0.3 (6)
C8—C9—C10—N1	179.1 (3)	C22—C23—C24—F1	179.5 (3)
C8—C9—C10—C5	−1.0 (5)	C23—C24—C25—C26	−0.3 (5)
N1—C2—C11—C16	69.2 (4)	F1—C24—C25—C26	179.9 (3)
C3—C2—C11—C16	−113.1 (4)	C24—C25—C26—C21	−0.3 (5)
N1—C2—C11—C12	−107.4 (4)	C22—C21—C26—C25	1.5 (5)
C3—C2—C11—C12	70.3 (5)	C3—C21—C26—C25	178.9 (3)
C16—C11—C12—C13	−4.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N14i	1.01	2.16	3.137 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N17—H17⋯N14i	1.01	2.16	3.137 (4)	162

Symmetry code: (i) .