N-[(2-Chloro-3-quinol-yl)meth-yl]-4-fluoro-aniline.

In the title compound, C(16)H(12)ClFN(2), the dihedral angle between the quinoline ring system and the flourophenyl ring is 86.70 (4)°. In the crystal, mol-ecules are linked into chains along the a axis by N-H⋯N hydrogen bonds. In addition, C-H⋯π inter-actions involving the two benzene rings are observed.

Related literature

For general background, properties and the biological activity of quinolines, see: Campbell et al. (1988 ▶); Dutta et al. (2002 ▶); Markees et al. (1970 ▶); Meth-Cohn et al. (1981 ▶); Michael et al. (1997 ▶); Morimoto et al. (1991 ▶); Padwa et al. (1999 ▶); Rajendran & Karavembu (2002 ▶); Robert & Meunier et al. (1998 ▶). For the synthesis of quinolines, see: Kouznetsov et al. (2005 ▶). For related structures, see: Butcher et al. 2007 ▶); Lynch et al. (2001 ▶); Subashini et al. (2009 ▶); Yathirajan et al. (2007 ▶); Wu et al. (2009 ▶); Khan et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶) .

Experimental

Crystal data

C16H12ClFN2

M = 286.73

Triclinic,

a = 7.3661 (8) Å

b = 8.8967 (9) Å

c = 11.5129 (12) Å

α = 68.704 (1)°

β = 74.468 (1)°

γ = 75.445 (1)°

V = 667.25 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.55 × 0.50 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.858, T max = 0.932

8162 measured reflections

3930 independent reflections

3633 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.03

3930 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036056/ci5158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036056/ci5158Isup2.hkl

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

C16H12ClFN2	Z = 2
Mr = 286.73	F(000) = 296
Triclinic, P1	Dx = 1.427 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3661 (8) Å	Cell parameters from 5222 reflections
b = 8.8967 (9) Å	θ = 2.5–31.0°
c = 11.5129 (12) Å	µ = 0.29 mm−1
α = 68.704 (1)°	T = 100 K
β = 74.468 (1)°	Plate, colourless
γ = 75.445 (1)°	0.55 × 0.50 × 0.25 mm
V = 667.25 (12) Å3

Bruker APEXII CCD area-detector diffractometer	3930 independent reflections
Radiation source: fine-focus sealed tube	3633 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω scans	θmax = 31.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.858, Tmax = 0.932	k = −12→12
8162 measured reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.2404P] where P = (Fo2 + 2Fc2)/3
3930 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	1.15120 (4)	−0.21591 (3)	0.79554 (2)	0.02245 (8)
N1	1.24567 (12)	0.03932 (10)	0.60973 (8)	0.01634 (16)
N2	0.55793 (12)	0.03799 (11)	0.74940 (8)	0.01744 (17)
H18	0.4905	0.0291	0.7025	0.021*
F1	0.24347 (10)	0.46529 (9)	1.02706 (7)	0.02663 (16)
C7	1.09918 (14)	−0.03020 (11)	0.67819 (9)	0.01494 (17)
C1	1.02460 (14)	0.25805 (11)	0.49326 (9)	0.01455 (17)
C10	0.74539 (14)	−0.05999 (12)	0.75411 (9)	0.01625 (18)
H10A	0.7513	−0.1557	0.7308	0.020*
H10B	0.7657	−0.0977	0.8407	0.020*
C8	0.90473 (13)	0.03112 (11)	0.66692 (9)	0.01406 (17)
C5	1.36831 (15)	0.26375 (13)	0.44050 (10)	0.01949 (19)
H5	1.4913	0.2165	0.4552	0.023*
C6	1.21153 (14)	0.18553 (12)	0.51570 (9)	0.01520 (17)
C9	0.87191 (13)	0.17731 (12)	0.57294 (9)	0.01522 (17)
H9	0.7474	0.2240	0.5615	0.018*
C14	0.21346 (15)	0.33659 (13)	0.88812 (10)	0.0206 (2)
H14	0.0879	0.3910	0.8882	0.025*
C11	0.48346 (14)	0.14581 (12)	0.81816 (9)	0.01552 (18)
C2	0.99836 (15)	0.40819 (12)	0.39406 (9)	0.01792 (19)
H17	0.8764	0.4568	0.3777	0.022*
C13	0.32377 (16)	0.36116 (12)	0.95720 (10)	0.01941 (19)
C3	1.15214 (16)	0.48201 (13)	0.32212 (10)	0.01972 (19)
H3	1.1338	0.5806	0.2572	0.024*
C12	0.59034 (14)	0.17592 (12)	0.88891 (9)	0.01760 (18)
H12	0.7166	0.1235	0.8889	0.021*
C4	1.33828 (16)	0.40979 (13)	0.34565 (10)	0.0210 (2)
H4	1.4413	0.4616	0.2965	0.025*
C15	0.29365 (14)	0.22899 (13)	0.81854 (10)	0.01916 (19)
H15	0.2208	0.2116	0.7714	0.023*
C16	0.50987 (15)	0.28339 (13)	0.95926 (10)	0.01933 (19)
H16	0.5809	0.3021	1.0068	0.023*

	U11	U22	U33	U12	U13	U23
Cl1	0.01931 (13)	0.01748 (12)	0.02433 (13)	−0.00220 (9)	−0.00775 (9)	0.00240 (9)
N1	0.0150 (4)	0.0161 (4)	0.0176 (4)	−0.0027 (3)	−0.0047 (3)	−0.0039 (3)
N2	0.0128 (4)	0.0214 (4)	0.0208 (4)	−0.0023 (3)	−0.0036 (3)	−0.0099 (3)
F1	0.0308 (4)	0.0241 (3)	0.0268 (3)	−0.0030 (3)	−0.0011 (3)	−0.0146 (3)
C7	0.0154 (4)	0.0129 (4)	0.0162 (4)	−0.0015 (3)	−0.0049 (3)	−0.0037 (3)
C1	0.0149 (4)	0.0143 (4)	0.0149 (4)	−0.0024 (3)	−0.0030 (3)	−0.0052 (3)
C10	0.0139 (4)	0.0152 (4)	0.0183 (4)	−0.0028 (3)	−0.0019 (3)	−0.0045 (3)
C8	0.0137 (4)	0.0142 (4)	0.0148 (4)	−0.0028 (3)	−0.0028 (3)	−0.0049 (3)
C5	0.0159 (4)	0.0216 (5)	0.0208 (5)	−0.0063 (4)	−0.0028 (3)	−0.0050 (4)
C6	0.0147 (4)	0.0157 (4)	0.0161 (4)	−0.0033 (3)	−0.0033 (3)	−0.0054 (3)
C9	0.0134 (4)	0.0156 (4)	0.0164 (4)	−0.0016 (3)	−0.0037 (3)	−0.0049 (3)
C14	0.0181 (4)	0.0211 (5)	0.0200 (5)	−0.0001 (4)	−0.0030 (4)	−0.0063 (4)
C11	0.0152 (4)	0.0152 (4)	0.0143 (4)	−0.0044 (3)	−0.0012 (3)	−0.0025 (3)
C2	0.0197 (4)	0.0159 (4)	0.0169 (4)	−0.0022 (3)	−0.0044 (3)	−0.0035 (3)
C13	0.0242 (5)	0.0161 (4)	0.0165 (4)	−0.0047 (4)	−0.0001 (4)	−0.0054 (3)
C3	0.0239 (5)	0.0166 (4)	0.0174 (4)	−0.0054 (4)	−0.0037 (4)	−0.0029 (3)
C12	0.0165 (4)	0.0180 (4)	0.0180 (4)	−0.0051 (3)	−0.0030 (3)	−0.0043 (3)
C4	0.0210 (5)	0.0212 (5)	0.0202 (5)	−0.0088 (4)	−0.0012 (4)	−0.0043 (4)
C15	0.0165 (4)	0.0220 (5)	0.0196 (4)	−0.0016 (4)	−0.0051 (3)	−0.0073 (4)
C16	0.0221 (5)	0.0199 (4)	0.0175 (4)	−0.0077 (4)	−0.0037 (4)	−0.0050 (4)

Cl1—C7	1.7434 (10)	C5—H5	0.93
N1—C7	1.3016 (13)	C9—H9	0.93
N1—C6	1.3732 (12)	C14—C13	1.3792 (15)
N2—C11	1.3792 (12)	C14—C15	1.3878 (14)
N2—C10	1.4388 (13)	C14—H14	0.93
N2—H18	0.86	C11—C12	1.4011 (14)
F1—C13	1.3661 (12)	C11—C15	1.4077 (14)
C7—C8	1.4217 (13)	C2—C3	1.3700 (14)
C1—C9	1.4133 (13)	C2—H17	0.93
C1—C6	1.4149 (13)	C13—C16	1.3737 (15)
C1—C2	1.4164 (13)	C3—C4	1.4128 (15)
C10—C8	1.5161 (13)	C3—H3	0.93
C10—H10A	0.97	C12—C16	1.3936 (14)
C10—H10B	0.97	C12—H12	0.93
C8—C9	1.3714 (13)	C4—H4	0.93
C5—C4	1.3726 (15)	C15—H15	0.93
C5—C6	1.4136 (13)	C16—H16	0.93
C7—N1—C6	117.48 (8)	C13—C14—C15	118.66 (10)
C11—N2—C10	121.76 (8)	C13—C14—H14	120.7
C11—N2—H18	119.1	C15—C14—H14	120.7
C10—N2—H18	119.1	N2—C11—C12	122.23 (9)
N1—C7—C8	126.51 (9)	N2—C11—C15	119.59 (9)
N1—C7—Cl1	115.47 (7)	C12—C11—C15	118.18 (9)
C8—C7—Cl1	118.01 (7)	C3—C2—C1	120.15 (9)
C9—C1—C6	117.92 (9)	C3—C2—H17	119.9
C9—C1—C2	123.09 (9)	C1—C2—H17	119.9
C6—C1—C2	118.98 (9)	F1—C13—C16	119.13 (9)
N2—C10—C8	113.32 (8)	F1—C13—C14	118.49 (9)
N2—C10—H10A	108.9	C16—C13—C14	122.38 (10)
C8—C10—H10A	108.9	C2—C3—C4	120.64 (9)
N2—C10—H10B	108.9	C2—C3—H3	119.7
C8—C10—H10B	108.9	C4—C3—H3	119.7
H10A—C10—H10B	107.7	C16—C12—C11	120.86 (9)
C9—C8—C7	115.61 (8)	C16—C12—H12	119.6
C9—C8—C10	122.70 (8)	C11—C12—H12	119.6
C7—C8—C10	121.69 (8)	C5—C4—C3	120.52 (9)
C4—C5—C6	119.71 (9)	C5—C4—H4	119.7
C4—C5—H5	120.1	C3—C4—H4	119.7
C6—C5—H5	120.1	C14—C15—C11	121.05 (9)
N1—C6—C5	118.51 (9)	C14—C15—H15	119.5
N1—C6—C1	121.50 (9)	C11—C15—H15	119.5
C5—C6—C1	119.99 (9)	C13—C16—C12	118.87 (9)
C8—C9—C1	120.95 (9)	C13—C16—H16	120.6
C8—C9—H9	119.5	C12—C16—H16	120.6
C1—C9—H9	119.5
C6—N1—C7—C8	−0.94 (15)	C6—C1—C9—C8	−1.63 (14)
C6—N1—C7—Cl1	179.70 (7)	C2—C1—C9—C8	179.30 (9)
C11—N2—C10—C8	−82.06 (11)	C10—N2—C11—C12	4.96 (14)
N1—C7—C8—C9	0.82 (15)	C10—N2—C11—C15	−174.83 (9)
Cl1—C7—C8—C9	−179.83 (7)	C9—C1—C2—C3	178.48 (9)
N1—C7—C8—C10	−178.91 (9)	C6—C1—C2—C3	−0.58 (15)
Cl1—C7—C8—C10	0.43 (13)	C15—C14—C13—F1	−179.04 (9)
N2—C10—C8—C9	−14.02 (13)	C15—C14—C13—C16	0.18 (16)
N2—C10—C8—C7	165.69 (9)	C1—C2—C3—C4	0.04 (16)
C7—N1—C6—C5	179.69 (9)	N2—C11—C12—C16	−178.83 (9)
C7—N1—C6—C1	−0.29 (14)	C15—C11—C12—C16	0.96 (14)
C4—C5—C6—N1	179.83 (9)	C6—C5—C4—C3	−0.37 (16)
C4—C5—C6—C1	−0.19 (15)	C2—C3—C4—C5	0.44 (16)
C9—C1—C6—N1	1.53 (14)	C13—C14—C15—C11	0.14 (16)
C2—C1—C6—N1	−179.36 (9)	N2—C11—C15—C14	179.10 (9)
C9—C1—C6—C5	−178.45 (9)	C12—C11—C15—C14	−0.70 (15)
C2—C1—C6—C5	0.65 (14)	F1—C13—C16—C12	179.30 (9)
C7—C8—C9—C1	0.55 (14)	C14—C13—C16—C12	0.08 (16)
C10—C8—C9—C1	−179.73 (8)	C11—C12—C16—C13	−0.67 (15)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H18···N1i	0.86	2.30	3.1353 (12)	165
C4—H4···Cg2ii	0.93	2.91	3.7494 (13)	151
C10—H10A···Cg1iii	0.97	2.62	3.5365 (12)	157
C10—H10B···Cg2iv	0.97	2.98	3.8083 (11)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H18⋯N1i	0.86	2.30	3.1353 (12)	165
C4—H4⋯Cg2ii	0.93	2.91	3.7494 (13)	151
C10—H10A⋯Cg1iii	0.97	2.62	3.5365 (12)	157
C10—H10B⋯Cg2iv	0.97	2.98	3.8083 (11)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .