4-(Adamantan-1-yl)-2-(4-fluoro-phen-yl)quinoline.

In the mol-ecule of the title compound, C25H24FN, the dihedral angle between the best planes of the quinoline fragment (rings A and B) and the benzene ring (C) is 9.51 (4)°. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of weak C-H⋯F inter-actions. The mol-ecules are stacked into chains along the a axis by weak off-set π-π inter-actions between the A and C rings of translation-related mol-ecules with a centroid-centroid distance of 3.6440 (2) Å.

Related literature

For the preparation and spectroscopic properties of the title compound, see: Kozubková et al. (2012 ▶). For related structures, see: Kozubková et al. (2012 ▶); Prabhuswamy et al. (2012 ▶). For the biological activity of related compounds, see: Nayyar et al. (2009 ▶).

Experimental

Crystal data

C25H24FN

M = 357.45

Triclinic,

a = 6.4604 (3) Å

b = 10.9964 (4) Å

c = 12.9074 (5) Å

α = 93.205 (3)°

β = 96.446 (3)°

γ = 100.507 (3)°

V = 893.14 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.60 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.971, T max = 1.000

9490 measured reflections

3142 independent reflections

2445 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1.08

3142 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012336/fy2093sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012336/fy2093Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012336/fy2093Isup3.cml

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

C25H24FN	Z = 2
Mr = 357.45	F(000) = 380
Triclinic, P1	Dx = 1.329 Mg m−3
Hall symbol: -P 1	Melting point: 435 K
a = 6.4604 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9964 (4) Å	Cell parameters from 5109 reflections
c = 12.9074 (5) Å	θ = 3.2–27.2°
α = 93.205 (3)°	µ = 0.08 mm−1
β = 96.446 (3)°	T = 120 K
γ = 100.507 (3)°	Block, colourless
V = 893.14 (6) Å3	0.60 × 0.40 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer	3142 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2445 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −8→13
Tmin = 0.971, Tmax = 1.000	l = −15→15
9490 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.20 e Å−3
3142 reflections	Δρmin = −0.19 e Å−3
244 parameters

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 > 2σ(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	0.34394 (12)	0.33553 (7)	0.56712 (6)	0.0332 (2)
N1	1.06928 (16)	0.26583 (10)	0.29611 (8)	0.0214 (3)
C1	0.92455 (19)	0.17633 (12)	0.32331 (9)	0.0198 (3)
C2	0.91382 (19)	0.05025 (12)	0.29032 (9)	0.0200 (3)
H2	0.8044	−0.0101	0.3110	0.024*
C3	1.05410 (19)	0.01109 (12)	0.22984 (9)	0.0187 (3)
C4	1.21873 (19)	0.10663 (12)	0.20249 (9)	0.0194 (3)
C5	1.39056 (19)	0.08736 (13)	0.14764 (9)	0.0213 (3)
H5	1.4001	0.0052	0.1247	0.026*
C6	1.5421 (2)	0.18375 (13)	0.12701 (9)	0.0243 (3)
H6	1.6546	0.1674	0.0902	0.029*
C7	1.5339 (2)	0.30672 (13)	0.15946 (10)	0.0261 (3)
H7	1.6392	0.3733	0.1441	0.031*
C8	1.3735 (2)	0.32951 (13)	0.21319 (10)	0.0244 (3)
H8	1.3678	0.4126	0.2351	0.029*
C9	1.21530 (19)	0.23188 (12)	0.23691 (9)	0.0202 (3)
C10	0.77164 (19)	0.21533 (12)	0.39064 (9)	0.0195 (3)
C11	0.8057 (2)	0.33784 (12)	0.43399 (10)	0.0236 (3)
H11	0.9288	0.3944	0.4218	0.028*
C12	0.6640 (2)	0.37833 (13)	0.49428 (10)	0.0250 (3)
H12	0.6889	0.4615	0.5240	0.030*
C13	0.4865 (2)	0.29515 (13)	0.51007 (9)	0.0236 (3)
C14	0.4466 (2)	0.17378 (13)	0.47036 (9)	0.0237 (3)
H14	0.3231	0.1181	0.4834	0.028*
C15	0.59069 (19)	0.13429 (12)	0.41086 (9)	0.0216 (3)
H15	0.5658	0.0503	0.3832	0.026*
C16	1.03604 (19)	−0.12759 (12)	0.19886 (9)	0.0180 (3)
C17	1.22648 (19)	−0.17477 (12)	0.25635 (9)	0.0197 (3)
H17A	1.3607	−0.1264	0.2383	0.024*
H17B	1.2260	−0.1621	0.3329	0.024*
C18	1.2147 (2)	−0.31265 (12)	0.22571 (9)	0.0218 (3)
H18	1.3411	−0.3403	0.2620	0.026*
C19	1.0124 (2)	−0.38832 (12)	0.25789 (9)	0.0230 (3)
H19A	1.0050	−0.4776	0.2390	0.028*
H19B	1.0131	−0.3763	0.3345	0.028*
C20	0.82066 (19)	−0.34565 (12)	0.20168 (9)	0.0214 (3)
H20	0.6879	−0.3938	0.2235	0.026*
C21	0.83436 (19)	−0.20723 (12)	0.23111 (9)	0.0203 (3)
H21A	0.8346	−0.1938	0.3076	0.024*
H21B	0.7076	−0.1804	0.1963	0.024*
C22	1.0223 (2)	−0.15445 (12)	0.07863 (9)	0.0207 (3)
H22A	0.8924	−0.1307	0.0441	0.025*
H22B	1.1463	−0.1039	0.0528	0.025*
C23	1.0176 (2)	−0.29224 (12)	0.05047 (9)	0.0220 (3)
H23	1.0164	−0.3067	−0.0268	0.026*
C24	0.8172 (2)	−0.36869 (13)	0.08344 (9)	0.0238 (3)
H24A	0.8113	−0.4579	0.0648	0.029*
H24B	0.6901	−0.3444	0.0465	0.029*
C25	1.2133 (2)	−0.33189 (13)	0.10712 (9)	0.0235 (3)
H25A	1.2110	−0.4204	0.0871	0.028*
H25B	1.3437	−0.2822	0.0862	0.028*

	U11	U22	U33	U12	U13	U23
F1	0.0378 (5)	0.0358 (5)	0.0331 (4)	0.0163 (4)	0.0192 (4)	0.0045 (4)
N1	0.0203 (6)	0.0218 (7)	0.0228 (5)	0.0056 (5)	0.0024 (4)	0.0036 (5)
C1	0.0184 (7)	0.0214 (8)	0.0192 (6)	0.0043 (6)	−0.0010 (5)	0.0032 (6)
C2	0.0183 (6)	0.0196 (8)	0.0221 (6)	0.0028 (6)	0.0040 (5)	0.0026 (6)
C3	0.0176 (6)	0.0214 (8)	0.0165 (6)	0.0034 (6)	0.0001 (5)	0.0022 (5)
C4	0.0194 (6)	0.0233 (8)	0.0154 (6)	0.0043 (6)	0.0000 (5)	0.0031 (5)
C5	0.0212 (7)	0.0244 (8)	0.0180 (6)	0.0034 (6)	0.0026 (5)	0.0015 (5)
C6	0.0208 (7)	0.0325 (9)	0.0195 (6)	0.0029 (6)	0.0051 (5)	0.0041 (6)
C7	0.0235 (7)	0.0271 (9)	0.0265 (7)	−0.0007 (6)	0.0051 (6)	0.0076 (6)
C8	0.0270 (7)	0.0185 (8)	0.0271 (7)	0.0020 (6)	0.0035 (6)	0.0049 (6)
C9	0.0192 (6)	0.0230 (8)	0.0187 (6)	0.0048 (6)	0.0008 (5)	0.0041 (6)
C10	0.0204 (7)	0.0202 (8)	0.0186 (6)	0.0065 (6)	0.0007 (5)	0.0017 (5)
C11	0.0229 (7)	0.0218 (8)	0.0261 (7)	0.0034 (6)	0.0035 (5)	0.0022 (6)
C12	0.0309 (8)	0.0217 (8)	0.0235 (7)	0.0087 (6)	0.0036 (6)	−0.0004 (6)
C13	0.0268 (7)	0.0306 (9)	0.0179 (6)	0.0139 (7)	0.0068 (5)	0.0040 (6)
C14	0.0226 (7)	0.0268 (9)	0.0230 (6)	0.0052 (6)	0.0056 (5)	0.0062 (6)
C15	0.0230 (7)	0.0202 (8)	0.0219 (6)	0.0056 (6)	0.0020 (5)	0.0012 (6)
C16	0.0172 (6)	0.0187 (8)	0.0183 (6)	0.0033 (6)	0.0044 (5)	0.0010 (5)
C17	0.0174 (6)	0.0236 (8)	0.0179 (6)	0.0033 (6)	0.0030 (5)	0.0003 (5)
C18	0.0220 (7)	0.0229 (8)	0.0222 (6)	0.0086 (6)	0.0029 (5)	0.0013 (6)
C19	0.0313 (7)	0.0183 (8)	0.0212 (6)	0.0068 (6)	0.0075 (5)	0.0008 (6)
C20	0.0194 (7)	0.0209 (8)	0.0236 (6)	0.0006 (6)	0.0077 (5)	0.0005 (6)
C21	0.0178 (6)	0.0224 (8)	0.0212 (6)	0.0043 (6)	0.0048 (5)	0.0005 (6)
C22	0.0188 (6)	0.0249 (8)	0.0179 (6)	0.0022 (6)	0.0026 (5)	0.0023 (5)
C23	0.0247 (7)	0.0253 (8)	0.0155 (6)	0.0033 (6)	0.0043 (5)	−0.0023 (5)
C24	0.0230 (7)	0.0240 (8)	0.0227 (7)	0.0017 (6)	0.0019 (5)	−0.0026 (6)
C25	0.0238 (7)	0.0222 (8)	0.0256 (7)	0.0052 (6)	0.0076 (5)	−0.0018 (6)

F1—C13	1.3610 (14)	C15—H15	0.9500
N1—C1	1.3201 (16)	C16—C21	1.5441 (16)
N1—C9	1.3681 (16)	C16—C17	1.5506 (16)
C1—C2	1.4144 (17)	C16—C22	1.5530 (15)
C1—C10	1.4901 (17)	C17—C18	1.5313 (17)
C2—C3	1.3710 (16)	C17—H17A	0.9900
C2—H2	0.9500	C17—H17B	0.9900
C3—C4	1.4414 (17)	C18—C19	1.5287 (17)
C3—C16	1.5348 (17)	C18—C25	1.5322 (16)
C4—C5	1.4227 (17)	C18—H18	1.0000
C4—C9	1.4282 (18)	C19—C20	1.5262 (17)
C5—C6	1.3654 (18)	C19—H19A	0.9900
C5—H5	0.9500	C19—H19B	0.9900
C6—C7	1.4051 (18)	C20—C24	1.5300 (16)
C6—H6	0.9500	C20—C21	1.5322 (17)
C7—C8	1.3617 (18)	C20—H20	1.0000
C7—H7	0.9500	C21—H21A	0.9900
C8—C9	1.4134 (18)	C21—H21B	0.9900
C8—H8	0.9500	C22—C23	1.5324 (17)
C10—C15	1.3941 (17)	C22—H22A	0.9900
C10—C11	1.3986 (18)	C22—H22B	0.9900
C11—C12	1.3826 (17)	C23—C24	1.5264 (17)
C11—H11	0.9500	C23—C25	1.5337 (17)
C12—C13	1.3727 (19)	C23—H23	1.0000
C12—H12	0.9500	C24—H24A	0.9900
C13—C14	1.3708 (18)	C24—H24B	0.9900
C14—C15	1.3838 (17)	C25—H25A	0.9900
C14—H14	0.9500	C25—H25B	0.9900
C1—N1—C9	117.34 (11)	C18—C17—H17A	109.5
N1—C1—C2	122.11 (11)	C16—C17—H17A	109.5
N1—C1—C10	116.32 (12)	C18—C17—H17B	109.5
C2—C1—C10	121.57 (11)	C16—C17—H17B	109.5
C3—C2—C1	123.02 (12)	H17A—C17—H17B	108.1
C3—C2—H2	118.5	C19—C18—C17	109.63 (10)
C1—C2—H2	118.5	C19—C18—C25	109.72 (10)
C2—C3—C4	115.91 (12)	C17—C18—C25	109.25 (10)
C2—C3—C16	120.26 (11)	C19—C18—H18	109.4
C4—C3—C16	123.79 (11)	C17—C18—H18	109.4
C5—C4—C9	116.54 (12)	C25—C18—H18	109.4
C5—C4—C3	125.90 (12)	C20—C19—C18	108.95 (10)
C9—C4—C3	117.51 (11)	C20—C19—H19A	109.9
C6—C5—C4	121.80 (13)	C18—C19—H19A	109.9
C6—C5—H5	119.1	C20—C19—H19B	109.9
C4—C5—H5	119.1	C18—C19—H19B	109.9
C5—C6—C7	120.96 (12)	H19A—C19—H19B	108.3
C5—C6—H6	119.5	C19—C20—C24	109.41 (10)
C7—C6—H6	119.5	C19—C20—C21	109.41 (10)
C8—C7—C6	119.30 (13)	C24—C20—C21	110.10 (10)
C8—C7—H7	120.4	C19—C20—H20	109.3
C6—C7—H7	120.4	C24—C20—H20	109.3
C7—C8—C9	121.27 (13)	C21—C20—H20	109.3
C7—C8—H8	119.4	C20—C21—C16	111.83 (10)
C9—C8—H8	119.4	C20—C21—H21A	109.3
N1—C9—C8	115.81 (12)	C16—C21—H21A	109.3
N1—C9—C4	124.04 (12)	C20—C21—H21B	109.3
C8—C9—C4	120.11 (11)	C16—C21—H21B	109.3
C15—C10—C11	117.95 (12)	H21A—C21—H21B	107.9
C15—C10—C1	122.31 (12)	C23—C22—C16	110.71 (10)
C11—C10—C1	119.73 (11)	C23—C22—H22A	109.5
C12—C11—C10	121.36 (12)	C16—C22—H22A	109.5
C12—C11—H11	119.3	C23—C22—H22B	109.5
C10—C11—H11	119.3	C16—C22—H22B	109.5
C13—C12—C11	118.23 (13)	H22A—C22—H22B	108.1
C13—C12—H12	120.9	C24—C23—C22	109.06 (10)
C11—C12—H12	120.9	C24—C23—C25	109.39 (10)
F1—C13—C14	118.85 (12)	C22—C23—C25	110.17 (10)
F1—C13—C12	118.38 (12)	C24—C23—H23	109.4
C14—C13—C12	122.77 (12)	C22—C23—H23	109.4
C13—C14—C15	118.37 (12)	C25—C23—H23	109.4
C13—C14—H14	120.8	C23—C24—C20	108.93 (10)
C15—C14—H14	120.8	C23—C24—H24A	109.9
C14—C15—C10	121.32 (13)	C20—C24—H24A	109.9
C14—C15—H15	119.3	C23—C24—H24B	109.9
C10—C15—H15	119.3	C20—C24—H24B	109.9
C3—C16—C21	112.40 (10)	H24A—C24—H24B	108.3
C3—C16—C17	109.61 (10)	C18—C25—C23	109.93 (10)
C21—C16—C17	106.18 (10)	C18—C25—H25A	109.7
C3—C16—C22	111.85 (10)	C23—C25—H25A	109.7
C21—C16—C22	105.68 (10)	C18—C25—H25B	109.7
C17—C16—C22	110.94 (10)	C23—C25—H25B	109.7
C18—C17—C16	110.84 (10)	H25A—C25—H25B	108.2
C9—N1—C1—C2	−2.15 (17)	C11—C10—C15—C14	1.14 (18)
C9—N1—C1—C10	178.09 (10)	C1—C10—C15—C14	−177.50 (11)
N1—C1—C2—C3	1.36 (18)	C2—C3—C16—C21	7.19 (15)
C10—C1—C2—C3	−178.88 (11)	C4—C3—C16—C21	−175.40 (10)
C1—C2—C3—C4	1.05 (17)	C2—C3—C16—C17	−110.64 (12)
C1—C2—C3—C16	178.66 (10)	C4—C3—C16—C17	66.78 (13)
C2—C3—C4—C5	174.85 (11)	C2—C3—C16—C22	125.88 (12)
C16—C3—C4—C5	−2.67 (18)	C4—C3—C16—C22	−56.70 (14)
C2—C3—C4—C9	−2.43 (15)	C3—C16—C17—C18	−179.14 (9)
C16—C3—C4—C9	−179.94 (10)	C21—C16—C17—C18	59.23 (12)
C9—C4—C5—C6	−1.31 (17)	C22—C16—C17—C18	−55.13 (13)
C3—C4—C5—C6	−178.61 (11)	C16—C17—C18—C19	−61.68 (12)
C4—C5—C6—C7	−0.01 (18)	C16—C17—C18—C25	58.58 (12)
C5—C6—C7—C8	0.69 (18)	C17—C18—C19—C20	60.25 (12)
C6—C7—C8—C9	0.01 (18)	C25—C18—C19—C20	−59.73 (13)
C1—N1—C9—C8	−177.26 (10)	C18—C19—C20—C24	61.41 (13)
C1—N1—C9—C4	0.59 (17)	C18—C19—C20—C21	−59.29 (12)
C7—C8—C9—N1	176.56 (11)	C19—C20—C21—C16	60.65 (12)
C7—C8—C9—C4	−1.39 (18)	C24—C20—C21—C16	−59.63 (13)
C5—C4—C9—N1	−175.79 (10)	C3—C16—C21—C20	−178.86 (9)
C3—C4—C9—N1	1.74 (17)	C17—C16—C21—C20	−59.02 (12)
C5—C4—C9—C8	1.98 (16)	C22—C16—C21—C20	58.88 (12)
C3—C4—C9—C8	179.51 (10)	C3—C16—C22—C23	176.68 (10)
N1—C1—C10—C15	169.13 (10)	C21—C16—C22—C23	−60.71 (12)
C2—C1—C10—C15	−10.64 (18)	C17—C16—C22—C23	53.95 (13)
N1—C1—C10—C11	−9.49 (16)	C16—C22—C23—C24	63.30 (12)
C2—C1—C10—C11	170.75 (10)	C16—C22—C23—C25	−56.77 (13)
C15—C10—C11—C12	−0.61 (18)	C22—C23—C24—C20	−60.27 (13)
C1—C10—C11—C12	178.06 (11)	C25—C23—C24—C20	60.28 (14)
C10—C11—C12—C13	−0.57 (19)	C19—C20—C24—C23	−61.85 (14)
C11—C12—C13—F1	−178.33 (11)	C21—C20—C24—C23	58.43 (13)
C11—C12—C13—C14	1.30 (19)	C19—C18—C25—C23	58.80 (14)
F1—C13—C14—C15	178.84 (11)	C17—C18—C25—C23	−61.41 (13)
C12—C13—C14—C15	−0.79 (19)	C24—C23—C25—C18	−59.05 (14)
C13—C14—C15—C10	−0.47 (18)	C22—C23—C25—C18	60.83 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F1i	0.95	2.61	3.2955 (12)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F1i	0.95	2.61	3.2955 (12)	129

Symmetry code: (i) .