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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3175
https://doi.org/10.1107/S1600536811045521

N-(4-Chloro­phen­yl)quinolin-2-amine

Zainal Abidin Hasan,a Zanariah Abdullah,a‡ Hairul Anuar Tajuddin,a Seik Weng Nga,b and Edward R. T. Tiekinka*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 24 October 2011; accepted 29 October 2011; online 5 November 2011)

There is a twist in the title mol­ecule, C15H11ClN2, 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 mol­ecule. In the crystal, supra­molecular layers in the ab plane are mediated by C—H⋯π inter­actions.

Related literature

For the structure of a related pyridine amine derivative, see: Aznan Akhmad et al. (2010[Aznan Akhmad, M. A., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2400.]).

[Scheme 1]

Experimental

Crystal data

  • C15H11ClN2

  • Mr = 254.71

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.872, Tmax = 1

  • 10754 measured reflections

  • 2726 independent reflections

  • 2460 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 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

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

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811045521/hb6472sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045521/hb6472Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045521/hb6472Isup3.cml

checkCIF report


Comment top

As a part of on-going studies of nitropyridine derivatives (Aznan Akhmad et al., 2010), the title compound was synthesized and structurally characterized. In (I), Fig. 1, the dihedral angle between the quinolinyl [r.m.s. deviation for the 10 non-hydrogen atoms = 0.022 Å] and benzene rings is 18.85 (9) Å indicating a twist in the molecule. The amine-H and quinolinyl-N atoms are directed towards opposite sides of the molecule. The quinolinyl-N atom participates in a close intramolecular C—H···N contact, Table 1. The amine-H atom is flanked by aromatic residues precluding its participation in close intermolecular contacts. The molecules are connected into supramolecular layers in the ab plane via C—H···π interactions, Fig. 2 and Table 1. Layers are connected along the c axis via weak C—H···Cl contacts, with the shortest of these being a C12—H12···Cl1i contact of 2.92 Å [C12···Cl1i = 3.655 (3) Å with angle at H12 = 135 °, for i: 1 + x, 1/2 - y, -1/2 + z], Fig. 3.

Related literature top

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

Experimental top

2-Chloroquinoline (1.0 g, 0.006 mol) was added to a solution of 4-chloroaniline (0.78 g, 0.006 mol) in ethanol (10 ml), and the mixture was refluxed for 7 h. The mixture was then cooled and the solvent evaporated off. The residue was dissolved in water and then extracted with diethyl ether (3 x 10 ml). The ether extracts were washed with water (3 x 10 ml) and dried over anhydrous sodium sulfate. Evaporation of the solvent gave the product and crystallization from its ethanol solution gave colourless prisms.

Refinement top

Carbon-bound hydrogen atoms were placed at calculated positions (C—H 0.95 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2 times Ueq(C). The amine-H atom was refined with N—H = 0.86±0.01 Å with refined Uiso.

Structure description top

As a part of on-going studies of nitropyridine derivatives (Aznan Akhmad et al., 2010), the title compound was synthesized and structurally characterized. In (I), Fig. 1, the dihedral angle between the quinolinyl [r.m.s. deviation for the 10 non-hydrogen atoms = 0.022 Å] and benzene rings is 18.85 (9) Å indicating a twist in the molecule. The amine-H and quinolinyl-N atoms are directed towards opposite sides of the molecule. The quinolinyl-N atom participates in a close intramolecular C—H···N contact, Table 1. The amine-H atom is flanked by aromatic residues precluding its participation in close intermolecular contacts. The molecules are connected into supramolecular layers in the ab plane via C—H···π interactions, Fig. 2 and Table 1. Layers are connected along the c axis via weak C—H···Cl contacts, with the shortest of these being a C12—H12···Cl1i contact of 2.92 Å [C12···Cl1i = 3.655 (3) Å with angle at H12 = 135 °, for i: 1 + x, 1/2 - y, -1/2 + z], Fig. 3.

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Layers in the ab plane in (I) sustained by C—H···π interactions shown as orange dashed lines.
[Figure 3] Fig. 3. Unit-cell contents for (I) shown in projection down the a axis highlighting the stacking of layers. The C—H···π interactions are shown as orange dashed lines.
N-(4-Chlorophenyl)quinolin-2-amine top
Crystal data top
C15H11ClN2F(000) = 528
Mr = 254.71Dx = 1.419 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5281 reflections
a = 5.9565 (4) Åθ = 2.7–28.8°
b = 7.9936 (6) ŵ = 0.30 mm−1
c = 25.0603 (18) ÅT = 100 K
β = 92.744 (1)°Prism, colourless
V = 1191.85 (15) Å30.2 × 0.1 × 0.1 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		2726 independent reflections
Radiation source: fine-focus sealed tube2460 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −7→7
Tmin = 0.872, Tmax = 1k = −9→10
10754 measured reflectionsl = −32→31
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H 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 parametersΔρmax = 0.50 e Å−3
1 restraintΔρmin = −0.32 e Å−3
Crystal data top
C15H11ClN2V = 1191.85 (15) Å3
Mr = 254.71Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.9565 (4) ŵ = 0.30 mm−1
b = 7.9936 (6) ÅT = 100 K
c = 25.0603 (18) Å0.2 × 0.1 × 0.1 mm
β = 92.744 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2726 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2460 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 1Rint = 0.030
10754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.50 e Å−3
2726 reflectionsΔρmin = −0.32 e Å−3
167 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.28861 (10)0.29464 (9)0.44653 (2)0.02527 (18)
N10.8994 (3)0.5543 (3)0.28636 (8)0.0188 (4)
H1n1.015 (4)0.601 (4)0.3019 (11)0.032 (9)*
N20.7753 (3)0.4313 (2)0.20524 (8)0.0162 (4)
C10.7450 (4)0.4911 (3)0.32189 (9)0.0155 (4)
C20.5367 (4)0.4212 (3)0.30617 (9)0.0170 (5)
H20.49110.41480.26940.020*
C30.3967 (4)0.3611 (3)0.34480 (9)0.0174 (5)
H30.25540.31310.33440.021*
C40.4632 (4)0.3714 (3)0.39834 (9)0.0173 (5)
C50.6687 (4)0.4413 (3)0.41464 (9)0.0177 (5)
H50.71320.44790.45150.021*
C60.8072 (4)0.5010 (3)0.37631 (9)0.0175 (5)
H60.94750.54980.38710.021*
C70.9269 (4)0.5194 (3)0.23314 (9)0.0161 (5)
C81.1286 (4)0.5837 (3)0.21166 (10)0.0187 (5)
H81.23040.64920.23320.022*
C91.1715 (4)0.5496 (3)0.16038 (10)0.0187 (5)
H91.30590.58910.14580.022*
C101.0152 (4)0.4543 (3)0.12822 (9)0.0165 (5)
C111.0462 (4)0.4160 (3)0.07422 (9)0.0192 (5)
H111.17990.45050.05820.023*
C120.8849 (4)0.3294 (3)0.04451 (9)0.0202 (5)
H120.90650.30450.00800.024*
C130.6878 (4)0.2778 (3)0.06850 (10)0.0195 (5)
H130.57540.21940.04780.023*
C140.6552 (4)0.3104 (3)0.12125 (9)0.0181 (5)
H140.52250.27180.13680.022*
C150.8163 (4)0.4006 (3)0.15264 (9)0.0151 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0228 (3)0.0326 (4)0.0205 (3)−0.0052 (3)0.0018 (2)0.0039 (2)
N10.0163 (10)0.0204 (11)0.0195 (10)−0.0052 (8)−0.0010 (8)−0.0027 (8)
N20.0159 (9)0.0145 (9)0.0181 (9)−0.0013 (7)−0.0003 (7)0.0009 (7)
C10.0143 (10)0.0114 (10)0.0207 (11)0.0013 (8)0.0012 (8)−0.0004 (8)
C20.0172 (11)0.0155 (11)0.0179 (11)0.0027 (9)−0.0025 (8)−0.0019 (9)
C30.0146 (10)0.0155 (11)0.0221 (11)0.0017 (9)−0.0001 (8)−0.0009 (9)
C40.0170 (11)0.0146 (11)0.0204 (11)0.0007 (9)0.0036 (9)0.0008 (9)
C50.0185 (11)0.0157 (11)0.0187 (11)0.0035 (9)−0.0017 (8)−0.0023 (9)
C60.0153 (10)0.0146 (11)0.0223 (11)0.0002 (8)−0.0023 (8)−0.0032 (9)
C70.0155 (10)0.0138 (11)0.0189 (11)0.0017 (9)−0.0008 (8)0.0023 (9)
C80.0171 (11)0.0155 (11)0.0232 (12)−0.0031 (9)−0.0025 (9)0.0017 (9)
C90.0147 (10)0.0164 (11)0.0250 (12)−0.0023 (9)0.0012 (9)0.0037 (9)
C100.0162 (11)0.0129 (11)0.0204 (11)0.0004 (9)0.0011 (8)0.0035 (9)
C110.0176 (11)0.0179 (12)0.0223 (12)0.0000 (9)0.0039 (9)0.0045 (9)
C120.0256 (12)0.0183 (12)0.0169 (11)0.0035 (10)0.0027 (9)0.0027 (9)
C130.0200 (11)0.0165 (11)0.0215 (11)−0.0009 (9)−0.0019 (9)0.0019 (9)
C140.0180 (11)0.0150 (11)0.0211 (11)−0.0023 (9)0.0000 (9)0.0023 (9)
C150.0156 (10)0.0117 (10)0.0179 (11)0.0018 (8)0.0002 (8)0.0040 (8)
Geometric parameters (Å, º) top
Cl1—C41.742 (2)C7—C81.435 (3)
N1—C71.380 (3)C8—C91.350 (3)
N1—C11.404 (3)C8—H80.9500
N1—H1n0.858 (10)C9—C101.423 (3)
N2—C71.319 (3)C9—H90.9500
N2—C151.374 (3)C10—C111.408 (3)
C1—C21.400 (3)C10—C151.425 (3)
C1—C61.398 (3)C11—C121.374 (3)
C2—C31.393 (3)C11—H110.9500
C2—H20.9500C12—C131.406 (3)
C3—C41.383 (3)C12—H120.9500
C3—H30.9500C13—C141.370 (3)
C4—C51.389 (3)C13—H130.9500
C5—C61.381 (3)C14—C151.410 (3)
C5—H50.9500C14—H140.9500
C6—H60.9500
C7—N1—C1130.7 (2)C9—C8—C7119.0 (2)
C7—N1—H1n113 (2)C9—C8—H8120.5
C1—N1—H1n114 (2)C7—C8—H8120.5
C7—N2—C15117.1 (2)C8—C9—C10119.9 (2)
C2—C1—C6119.1 (2)C8—C9—H9120.0
C2—C1—N1124.3 (2)C10—C9—H9120.0
C6—C1—N1116.6 (2)C11—C10—C9123.3 (2)
C3—C2—C1119.6 (2)C11—C10—C15119.8 (2)
C3—C2—H2120.2C9—C10—C15116.9 (2)
C1—C2—H2120.2C12—C11—C10120.7 (2)
C4—C3—C2120.0 (2)C12—C11—H11119.7
C4—C3—H3120.0C10—C11—H11119.7
C2—C3—H3120.0C11—C12—C13119.5 (2)
C5—C4—C3121.1 (2)C11—C12—H12120.3
C5—C4—Cl1119.00 (18)C13—C12—H12120.3
C3—C4—Cl1119.92 (18)C14—C13—C12121.1 (2)
C6—C5—C4118.8 (2)C14—C13—H13119.5
C6—C5—H5120.6C12—C13—H13119.5
C4—C5—H5120.6C13—C14—C15120.8 (2)
C5—C6—C1121.3 (2)C13—C14—H14119.6
C5—C6—H6119.3C15—C14—H14119.6
C1—C6—H6119.3N2—C15—C14118.6 (2)
N2—C7—N1120.7 (2)N2—C15—C10123.2 (2)
N2—C7—C8123.8 (2)C14—C15—C10118.2 (2)
N1—C7—C8115.5 (2)
C7—N1—C1—C2−23.3 (4)N1—C7—C8—C9177.6 (2)
C7—N1—C1—C6157.0 (2)C7—C8—C9—C101.3 (4)
C6—C1—C2—C3−0.8 (3)C8—C9—C10—C11178.9 (2)
N1—C1—C2—C3179.6 (2)C8—C9—C10—C150.6 (3)
C1—C2—C3—C40.3 (3)C9—C10—C11—C12−177.3 (2)
C2—C3—C4—C50.1 (4)C15—C10—C11—C120.9 (3)
C2—C3—C4—Cl1−179.50 (18)C10—C11—C12—C13−0.4 (4)
C3—C4—C5—C60.0 (4)C11—C12—C13—C14−0.9 (4)
Cl1—C4—C5—C6179.60 (18)C12—C13—C14—C151.7 (4)
C4—C5—C6—C1−0.5 (3)C7—N2—C15—C14−178.4 (2)
C2—C1—C6—C50.9 (3)C7—N2—C15—C102.2 (3)
N1—C1—C6—C5−179.4 (2)C13—C14—C15—N2179.5 (2)
C15—N2—C7—N1−179.4 (2)C13—C14—C15—C10−1.0 (3)
C15—N2—C7—C80.0 (3)C11—C10—C15—N2179.2 (2)
C1—N1—C7—N210.6 (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—C14178.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 Cg2 and Cg3 are the centroids of of the N1,C7–C10,C15, C10–C15 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···N20.952.392.961 (3)118
C3—H3···Cg1i0.952.943.734 (3)142
C9—H9···Cg2ii0.952.793.383 (3)121
C14—H14···Cg2i0.952.833.440 (3)123
C6—H6···Cg3ii0.952.813.590 (3)140
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC15H11ClN2
Mr254.71
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)5.9565 (4), 7.9936 (6), 25.0603 (18)
β (°) 92.744 (1)
V (Å3)1191.85 (15)
Z4
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.2 × 0.1 × 0.1
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.872, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections		10754, 2726, 2460
Rint0.030
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.134, 1.11
No. of reflections2726
No. of parameters167
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.50, −0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1 Cg2 and Cg3 are the centroids of of the N1,C7–C10,C15, C10–C15 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···N20.952.392.961 (3)118
C3—H3···Cg1i0.952.943.734 (3)142
C9—H9···Cg2ii0.952.793.383 (3)121
C14—H14···Cg2i0.952.833.440 (3)123
C6—H6···Cg3ii0.952.813.590 (3)140
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2.
 

Footnotes

‡Additional correspondence author, e-mail: zana@um.edu.my.

Acknowledgements

We thank the University of Malaya (grant No. RG027/09AFR) for supporting this study.

References

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 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3175
https://doi.org/10.1107/S1600536811045521
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