N-(4-Chloro-phen-yl)quinolin-2-amine.

There is a twist in the title mol-ecule, C(15)H(11)ClN(2), as seen in the dihedral angle of 18.85 (9)° between the quinoline and benzene rings. A short C-H⋯N contact arises from this conformation and the amine H and quinoline N atoms are directed towards opposite sides of the mol-ecule. In the crystal, supra-molecular layers in the ab plane are mediated by C-H⋯π inter-actions.

Related literature

For the structure of a related pyridine amine derivative, see: Aznan Akhmad et al. (2010 ▶).

Experimental

Crystal data

C15H11ClN2

M = 254.71

Monoclinic,

a = 5.9565 (4) Å

b = 7.9936 (6) Å

c = 25.0603 (18) Å

β = 92.744 (1)°

V = 1191.85 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.2 × 0.1 × 0.1 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.872, T max = 1

10754 measured reflections

2726 independent reflections

2460 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.134

S = 1.11

2726 reflections

167 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045521/hb6472sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045521/hb6472Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045521/hb6472Isup3.cml

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

C15H11ClN2	F(000) = 528
Mr = 254.71	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5281 reflections
a = 5.9565 (4) Å	θ = 2.7–28.8°
b = 7.9936 (6) Å	µ = 0.30 mm−1
c = 25.0603 (18) Å	T = 100 K
β = 92.744 (1)°	Prism, colourless
V = 1191.85 (15) Å3	0.2 × 0.1 × 0.1 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2726 independent reflections
Radiation source: fine-focus sealed tube	2460 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.872, Tmax = 1	k = −9→10
10754 measured reflections	l = −32→31

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0396P)2 + 2.5503P] where P = (Fo2 + 2Fc2)/3
2726 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.50 e Å−3
1 restraint	Δρmin = −0.32 e Å−3

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	0.28861 (10)	0.29464 (9)	0.44653 (2)	0.02527 (18)
N1	0.8994 (3)	0.5543 (3)	0.28636 (8)	0.0188 (4)
H1n	1.015 (4)	0.601 (4)	0.3019 (11)	0.032 (9)*
N2	0.7753 (3)	0.4313 (2)	0.20524 (8)	0.0162 (4)
C1	0.7450 (4)	0.4911 (3)	0.32189 (9)	0.0155 (4)
C2	0.5367 (4)	0.4212 (3)	0.30617 (9)	0.0170 (5)
H2	0.4911	0.4148	0.2694	0.020*
C3	0.3967 (4)	0.3611 (3)	0.34480 (9)	0.0174 (5)
H3	0.2554	0.3131	0.3344	0.021*
C4	0.4632 (4)	0.3714 (3)	0.39834 (9)	0.0173 (5)
C5	0.6687 (4)	0.4413 (3)	0.41464 (9)	0.0177 (5)
H5	0.7132	0.4479	0.4515	0.021*
C6	0.8072 (4)	0.5010 (3)	0.37631 (9)	0.0175 (5)
H6	0.9475	0.5498	0.3871	0.021*
C7	0.9269 (4)	0.5194 (3)	0.23314 (9)	0.0161 (5)
C8	1.1286 (4)	0.5837 (3)	0.21166 (10)	0.0187 (5)
H8	1.2304	0.6492	0.2332	0.022*
C9	1.1715 (4)	0.5496 (3)	0.16038 (10)	0.0187 (5)
H9	1.3059	0.5891	0.1458	0.022*
C10	1.0152 (4)	0.4543 (3)	0.12822 (9)	0.0165 (5)
C11	1.0462 (4)	0.4160 (3)	0.07422 (9)	0.0192 (5)
H11	1.1799	0.4505	0.0582	0.023*
C12	0.8849 (4)	0.3294 (3)	0.04451 (9)	0.0202 (5)
H12	0.9065	0.3045	0.0080	0.024*
C13	0.6878 (4)	0.2778 (3)	0.06850 (10)	0.0195 (5)
H13	0.5754	0.2194	0.0478	0.023*
C14	0.6552 (4)	0.3104 (3)	0.12125 (9)	0.0181 (5)
H14	0.5225	0.2718	0.1368	0.022*
C15	0.8163 (4)	0.4006 (3)	0.15264 (9)	0.0151 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0228 (3)	0.0326 (4)	0.0205 (3)	−0.0052 (3)	0.0018 (2)	0.0039 (2)
N1	0.0163 (10)	0.0204 (11)	0.0195 (10)	−0.0052 (8)	−0.0010 (8)	−0.0027 (8)
N2	0.0159 (9)	0.0145 (9)	0.0181 (9)	−0.0013 (7)	−0.0003 (7)	0.0009 (7)
C1	0.0143 (10)	0.0114 (10)	0.0207 (11)	0.0013 (8)	0.0012 (8)	−0.0004 (8)
C2	0.0172 (11)	0.0155 (11)	0.0179 (11)	0.0027 (9)	−0.0025 (8)	−0.0019 (9)
C3	0.0146 (10)	0.0155 (11)	0.0221 (11)	0.0017 (9)	−0.0001 (8)	−0.0009 (9)
C4	0.0170 (11)	0.0146 (11)	0.0204 (11)	0.0007 (9)	0.0036 (9)	0.0008 (9)
C5	0.0185 (11)	0.0157 (11)	0.0187 (11)	0.0035 (9)	−0.0017 (8)	−0.0023 (9)
C6	0.0153 (10)	0.0146 (11)	0.0223 (11)	0.0002 (8)	−0.0023 (8)	−0.0032 (9)
C7	0.0155 (10)	0.0138 (11)	0.0189 (11)	0.0017 (9)	−0.0008 (8)	0.0023 (9)
C8	0.0171 (11)	0.0155 (11)	0.0232 (12)	−0.0031 (9)	−0.0025 (9)	0.0017 (9)
C9	0.0147 (10)	0.0164 (11)	0.0250 (12)	−0.0023 (9)	0.0012 (9)	0.0037 (9)
C10	0.0162 (11)	0.0129 (11)	0.0204 (11)	0.0004 (9)	0.0011 (8)	0.0035 (9)
C11	0.0176 (11)	0.0179 (12)	0.0223 (12)	0.0000 (9)	0.0039 (9)	0.0045 (9)
C12	0.0256 (12)	0.0183 (12)	0.0169 (11)	0.0035 (10)	0.0027 (9)	0.0027 (9)
C13	0.0200 (11)	0.0165 (11)	0.0215 (11)	−0.0009 (9)	−0.0019 (9)	0.0019 (9)
C14	0.0180 (11)	0.0150 (11)	0.0211 (11)	−0.0023 (9)	0.0000 (9)	0.0023 (9)
C15	0.0156 (10)	0.0117 (10)	0.0179 (11)	0.0018 (8)	0.0002 (8)	0.0040 (8)

Cl1—C4	1.742 (2)	C7—C8	1.435 (3)
N1—C7	1.380 (3)	C8—C9	1.350 (3)
N1—C1	1.404 (3)	C8—H8	0.9500
N1—H1n	0.858 (10)	C9—C10	1.423 (3)
N2—C7	1.319 (3)	C9—H9	0.9500
N2—C15	1.374 (3)	C10—C11	1.408 (3)
C1—C2	1.400 (3)	C10—C15	1.425 (3)
C1—C6	1.398 (3)	C11—C12	1.374 (3)
C2—C3	1.393 (3)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.406 (3)
C3—C4	1.383 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.370 (3)
C4—C5	1.389 (3)	C13—H13	0.9500
C5—C6	1.381 (3)	C14—C15	1.410 (3)
C5—H5	0.9500	C14—H14	0.9500
C6—H6	0.9500
C7—N1—C1	130.7 (2)	C9—C8—C7	119.0 (2)
C7—N1—H1n	113 (2)	C9—C8—H8	120.5
C1—N1—H1n	114 (2)	C7—C8—H8	120.5
C7—N2—C15	117.1 (2)	C8—C9—C10	119.9 (2)
C2—C1—C6	119.1 (2)	C8—C9—H9	120.0
C2—C1—N1	124.3 (2)	C10—C9—H9	120.0
C6—C1—N1	116.6 (2)	C11—C10—C9	123.3 (2)
C3—C2—C1	119.6 (2)	C11—C10—C15	119.8 (2)
C3—C2—H2	120.2	C9—C10—C15	116.9 (2)
C1—C2—H2	120.2	C12—C11—C10	120.7 (2)
C4—C3—C2	120.0 (2)	C12—C11—H11	119.7
C4—C3—H3	120.0	C10—C11—H11	119.7
C2—C3—H3	120.0	C11—C12—C13	119.5 (2)
C5—C4—C3	121.1 (2)	C11—C12—H12	120.3
C5—C4—Cl1	119.00 (18)	C13—C12—H12	120.3
C3—C4—Cl1	119.92 (18)	C14—C13—C12	121.1 (2)
C6—C5—C4	118.8 (2)	C14—C13—H13	119.5
C6—C5—H5	120.6	C12—C13—H13	119.5
C4—C5—H5	120.6	C13—C14—C15	120.8 (2)
C5—C6—C1	121.3 (2)	C13—C14—H14	119.6
C5—C6—H6	119.3	C15—C14—H14	119.6
C1—C6—H6	119.3	N2—C15—C14	118.6 (2)
N2—C7—N1	120.7 (2)	N2—C15—C10	123.2 (2)
N2—C7—C8	123.8 (2)	C14—C15—C10	118.2 (2)
N1—C7—C8	115.5 (2)
C7—N1—C1—C2	−23.3 (4)	N1—C7—C8—C9	177.6 (2)
C7—N1—C1—C6	157.0 (2)	C7—C8—C9—C10	1.3 (4)
C6—C1—C2—C3	−0.8 (3)	C8—C9—C10—C11	178.9 (2)
N1—C1—C2—C3	179.6 (2)	C8—C9—C10—C15	0.6 (3)
C1—C2—C3—C4	0.3 (3)	C9—C10—C11—C12	−177.3 (2)
C2—C3—C4—C5	0.1 (4)	C15—C10—C11—C12	0.9 (3)
C2—C3—C4—Cl1	−179.50 (18)	C10—C11—C12—C13	−0.4 (4)
C3—C4—C5—C6	0.0 (4)	C11—C12—C13—C14	−0.9 (4)
Cl1—C4—C5—C6	179.60 (18)	C12—C13—C14—C15	1.7 (4)
C4—C5—C6—C1	−0.5 (3)	C7—N2—C15—C14	−178.4 (2)
C2—C1—C6—C5	0.9 (3)	C7—N2—C15—C10	2.2 (3)
N1—C1—C6—C5	−179.4 (2)	C13—C14—C15—N2	179.5 (2)
C15—N2—C7—N1	−179.4 (2)	C13—C14—C15—C10	−1.0 (3)
C15—N2—C7—C8	0.0 (3)	C11—C10—C15—N2	179.2 (2)
C1—N1—C7—N2	10.6 (4)	C9—C10—C15—N2	−2.5 (3)
C1—N1—C7—C8	−168.8 (2)	C11—C10—C15—C14	−0.2 (3)
N2—C7—C8—C9	−1.8 (4)	C9—C10—C15—C14	178.1 (2)

Cg1 Cg2 and Cg3 are the centroids of of the N1,C7–C10,C15, C10–C15 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2	0.95	2.39	2.961 (3)	118
C3—H3···Cg1i	0.95	2.94	3.734 (3)	142
C9—H9···Cg2ii	0.95	2.79	3.383 (3)	121
C14—H14···Cg2i	0.95	2.83	3.440 (3)	123
C6—H6···Cg3ii	0.95	2.81	3.590 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 Cg2 and Cg3 are the centroids of of the N1,C7–C10,C15, C10–C15 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N2	0.95	2.39	2.961 (3)	118
C3—H3⋯Cg1i	0.95	2.94	3.734 (3)	142
C9—H9⋯Cg2ii	0.95	2.79	3.383 (3)	121
C14—H14⋯Cg2i	0.95	2.83	3.440 (3)	123
C6—H6⋯Cg3ii	0.95	2.81	3.590 (3)	140

Symmetry codes: (i) ; (ii) .