supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, o94    [ doi:10.1107/S1600536808041184 ]

4-Chloro-N-(pyrimidin-2-yl)aniline

A. B. Maizathul Akmam, Z. Abdullah and S. W. Ng

Abstract top

The two aromatic rings in the title compound, C10H8ClN3, open the angle at the planar N atom to 128.00 (12)°. The amino N atom of one molecule forms a hydrogen bond to the 1-N atom of an adjacent pyrimidyl ring, generating a hydrogen-bonded dimer.

Related literature top

For other 4-chloroanilino substituted N-heterocycles, see: Fairuz et al. (2008); Idris et al. (2008).

Experimental top

2-Chloropyrimidine (2.88 g, 2.5 mmol) and 4-chloroaniline (3.20 g, 25 mmol) were mixed with ethanol (2 ml) and the mixture was heated at 423–433 K for 8 h. The product was dissolved in water and the solution extracted with ether. The ether phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped crystals along with some unidentified brown material.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; its temperature factors were freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of hydrogen-bonded dimeric structure of C10H8ClN3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Hydrogen bonds are shown as red dashed lines.
4-Chloro-N-(pyrimidin-2-yl)aniline top
Crystal data top
C10H8ClN3Z = 2
Mr = 205.64F(000) = 212
Triclinic, P1Dx = 1.498 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.7750 (1) ÅCell parameters from 2160 reflections
b = 10.0589 (3) Åθ = 2.6–28.2°
c = 12.0116 (3) ŵ = 0.38 mm−1
α = 89.237 (1)°T = 100 K
β = 89.037 (1)°Plate, yellow
γ = 89.399 (2)°0.35 × 0.15 × 0.05 mm
V = 455.98 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer		2032 independent reflections
Radiation source: fine-focus sealed tube1757 reflections with I > 2σ(I)
graphiteRint = 0.014
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −4→4
Tmin = 0.880, Tmax = 0.982k = −13→13
3625 measured reflectionsl = −14→15
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0319P)2 + 0.3201P]
where P = (Fo2 + 2Fc2)/3
2032 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C10H8ClN3γ = 89.399 (2)°
Mr = 205.64V = 455.98 (2) Å3
Triclinic, P1Z = 2
a = 3.7750 (1) ÅMo Kα radiation
b = 10.0589 (3) ŵ = 0.38 mm−1
c = 12.0116 (3) ÅT = 100 K
α = 89.237 (1)°0.35 × 0.15 × 0.05 mm
β = 89.037 (1)°
Data collection top
Bruker SMART APEX
diffractometer		2032 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1757 reflections with I > 2σ(I)
Tmin = 0.880, Tmax = 0.982Rint = 0.014
3625 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080Δρmax = 0.34 e Å−3
S = 1.02Δρmin = −0.24 e Å−3
2032 reflectionsAbsolute structure: ?
131 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.12780 (11)0.77439 (4)1.04792 (3)0.02641 (13)
N10.6990 (3)0.63747 (13)0.59185 (10)0.0156 (3)
H10.642 (5)0.556 (2)0.5875 (16)0.028 (5)*
N20.5390 (3)0.64905 (12)0.40908 (10)0.0150 (3)
N30.7907 (3)0.83808 (12)0.49717 (10)0.0156 (3)
C10.8101 (4)0.67719 (14)0.69743 (11)0.0136 (3)
C20.7505 (4)0.80454 (15)0.73923 (11)0.0156 (3)
H20.64160.87100.69410.019*
C30.8504 (4)0.83405 (15)0.84683 (12)0.0178 (3)
H30.81170.92080.87520.021*
C41.0064 (4)0.73655 (16)0.91245 (11)0.0172 (3)
C51.0687 (4)0.60984 (15)0.87278 (12)0.0175 (3)
H51.17670.54360.91840.021*
C60.9703 (4)0.58131 (15)0.76498 (12)0.0156 (3)
H61.01310.49470.73680.019*
C70.6752 (4)0.71254 (14)0.49723 (11)0.0132 (3)
C80.7695 (4)0.90471 (14)0.40058 (12)0.0156 (3)
H80.84690.99430.39750.019*
C90.6401 (4)0.84960 (15)0.30478 (12)0.0165 (3)
H90.62960.89810.23650.020*
C100.5268 (4)0.71961 (15)0.31431 (11)0.0159 (3)
H100.43580.67850.25020.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0288 (2)0.0384 (2)0.01228 (18)−0.00173 (17)−0.00450 (14)−0.00490 (15)
N10.0213 (7)0.0124 (6)0.0133 (6)−0.0040 (5)−0.0022 (5)−0.0008 (5)
N20.0171 (6)0.0139 (6)0.0141 (6)−0.0007 (5)−0.0017 (5)−0.0020 (4)
N30.0169 (6)0.0151 (6)0.0146 (6)−0.0028 (5)0.0002 (5)−0.0010 (5)
C10.0129 (6)0.0158 (7)0.0121 (6)−0.0037 (5)0.0005 (5)−0.0004 (5)
C20.0173 (7)0.0159 (7)0.0136 (6)−0.0006 (5)0.0002 (5)0.0005 (5)
C30.0184 (7)0.0185 (7)0.0164 (7)−0.0019 (6)0.0022 (5)−0.0043 (5)
C40.0152 (7)0.0260 (8)0.0103 (6)−0.0035 (6)0.0003 (5)−0.0020 (5)
C50.0141 (7)0.0224 (8)0.0158 (7)−0.0005 (6)0.0003 (5)0.0030 (6)
C60.0153 (7)0.0154 (7)0.0162 (7)−0.0012 (5)0.0016 (5)−0.0009 (5)
C70.0118 (6)0.0145 (7)0.0133 (6)0.0001 (5)0.0007 (5)−0.0018 (5)
C80.0159 (7)0.0138 (7)0.0170 (7)−0.0013 (5)0.0017 (5)−0.0001 (5)
C90.0182 (7)0.0177 (7)0.0135 (6)0.0008 (6)0.0004 (5)0.0012 (5)
C100.0161 (7)0.0180 (7)0.0136 (6)0.0010 (5)−0.0019 (5)−0.0030 (5)
Geometric parameters (Å, °) top
Cl1—C41.7458 (14)C3—C41.383 (2)
N1—C71.3599 (18)C3—H30.9500
N1—C11.4067 (17)C4—C51.383 (2)
N1—H10.85 (2)C5—C61.3875 (19)
N2—C101.3346 (18)C5—H50.9500
N2—C71.3552 (17)C6—H60.9500
N3—C81.3353 (18)C8—C91.383 (2)
N3—C71.3404 (18)C8—H80.9500
C1—C61.392 (2)C9—C101.383 (2)
C1—C21.397 (2)C9—H90.9500
C2—C31.3890 (19)C10—H100.9500
C2—H20.9500
C7—N1—C1128.00 (12)C4—C5—H5120.7
C7—N1—H1116.9 (14)C6—C5—H5120.7
C1—N1—H1115.1 (14)C5—C6—C1121.22 (13)
C10—N2—C7115.63 (12)C5—C6—H6119.4
C8—N3—C7116.05 (12)C1—C6—H6119.4
C6—C1—C2119.06 (13)N3—C7—N2125.91 (13)
C6—C1—N1117.44 (13)N3—C7—N1119.22 (12)
C2—C1—N1123.41 (13)N2—C7—N1114.85 (12)
C3—C2—C1120.03 (14)N3—C8—C9123.14 (13)
C3—C2—H2120.0N3—C8—H8118.4
C1—C2—H2120.0C9—C8—H8118.4
C4—C3—C2119.69 (14)C10—C9—C8115.99 (13)
C4—C3—H3120.2C10—C9—H9122.0
C2—C3—H3120.2C8—C9—H9122.0
C5—C4—C3121.30 (13)N2—C10—C9123.27 (13)
C5—C4—Cl1119.40 (12)N2—C10—H10118.4
C3—C4—Cl1119.31 (12)C9—C10—H10118.4
C4—C5—C6118.70 (14)
C7—N1—C1—C6−150.50 (14)N1—C1—C6—C5−176.11 (13)
C7—N1—C1—C233.1 (2)C8—N3—C7—N2−0.4 (2)
C6—C1—C2—C3−0.1 (2)C8—N3—C7—N1178.01 (13)
N1—C1—C2—C3176.32 (13)C10—N2—C7—N31.0 (2)
C1—C2—C3—C4−0.5 (2)C10—N2—C7—N1−177.43 (13)
C2—C3—C4—C50.6 (2)C1—N1—C7—N35.1 (2)
C2—C3—C4—Cl1−179.51 (11)C1—N1—C7—N2−176.27 (13)
C3—C4—C5—C6−0.2 (2)C7—N3—C8—C9−0.6 (2)
Cl1—C4—C5—C6179.93 (11)N3—C8—C9—C100.8 (2)
C4—C5—C6—C1−0.4 (2)C7—N2—C10—C9−0.7 (2)
C2—C1—C6—C50.5 (2)C8—C9—C10—N2−0.1 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.85 (2)2.18 (2)3.028 (2)174 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.85 (2)2.18 (2)3.028 (2)174 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the University of Malaya for supporting this study (PS077/2007 C).

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Fairuz, M. Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1800.

Idris, A., Wan Saffiee, W. A. M., Abdullah, Z., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o2443.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.