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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 o3176
https://doi.org/10.1107/S1600536811045570

N-(4-Chloro­phen­yl)-3-nitro­pyridin-2-amine

Aina Mardia Akhmad Aznan,a Zainal Abidin Fairuz,a Zanariah Abdullah,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 30 October 2011; online 5 November 2011)

In the title compound, C11H8ClN3O2, the presence of intra­molecular N—H⋯O and C—H⋯N inter­actions help to establish an almost planar mol­ecule [dihedral angle between the pyridine and benzene rings = 9.89 (8)° and r.m.s. deviation for all 17 non-H atoms = 0.120 Å]. Supra­molecular tapes feature in the crystal packing whereby dimeric aggregates sustained by pairs of C—H⋯O inter­actions are connected by π–π inter­actions occurring between translationally related pyridine rings and between translationally related benzene rings along the b axis [centroid–centroid distance = length of b axis = 3.8032 (4) Å].

Related literature

For the structure of a related pyrimidine 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

  • C11H8ClN3O2

  • Mr = 249.65

  • Monoclinic, C 2/c

  • a = 30.472 (3) Å

  • b = 3.8032 (4) Å

  • c = 21.300 (2) Å

  • β = 123.153 (1)°

  • V = 2066.7 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.36 mm−1

  • T = 100 K

  • 0.40 × 0.15 × 0.05 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 = 0.869, Tmax = 0.982

  • 8919 measured reflections

  • 2347 independent reflections

  • 1912 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.091

  • S = 1.00

  • 2347 reflections

  • 158 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1n⋯O1 0.87 (2) 1.91 (2) 2.6280 (18) 138.2 (17)
C7—H7⋯N2 0.95 2.31 2.909 (2) 120
C3—H3⋯O2i 0.95 2.48 3.340 (3) 152
Symmetry code: (i) -x, -y+3, -z+1.

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/S1600536811045570/hb6473sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045570/hb6473Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045570/hb6473Isup3.cml

checkCIF report


Comment top

In connection with synthetic and structural studies of nitro-pyridine/pyrimidine derivatives (Aznan Akhmad et al., 2010), the title compound, (I), was investigated. A small twist is evident in (I), Fig. 1, as seen in the value of the dihedral angle between the pyridyl and benzene rings of 9.89 (8) Å. The nitro group is co-planar with the pyridyl ring to which it is connected: the O1—N3—C2—C1 torsion angle is 5.0 (2)°. The observed conformation is stabilized by an intramolecular N—H···O hydrogen bond as well as a C—H···N interaction, Table 1. Overall, the molecule is close to planar with the r.m.s. deviation for all 17 non-hydrogen atoms being 0.120 Å.

In the crystal structure, centrosymmetrically related molecules are connected into dimeric aggregates via C—H···O interactions, Table 1. These are connected into a supramolecular tape along the b axis by π–π interactions between translationally related pyridyl rings and between translationally related benzene rings with the centroid···centroid separation corresponding to the length of the b axis, i.e. 3.8032 (4) Å, Fig. 2. The columns are connected by weak C—H···Cl [closest contact: C5—H5···Cl1i = 3.97 Å, C5···Cl1i = 3.6112 (19) Å and angle at H5 = 124° for i: 1/2 - x, 3/2 - y, 1 - z] and Cl···Cl [Cl1···Cl1ii = 3.4366 (7) Å for ii: 1/2 - x, -1/2 + y, 1/2 - z] contacts. A view of the unit-cell contents is given in Fig. 3.

Related literature top

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

Experimental top

2-Chloro-3-nitro-pyridine (0.906 g, 0.0057 mol) and p-chloroaniline (0.730 g, 0.0057 mol) were refluxed in ethanol (5 ml) for 4 h at 385 K. After cooling the mixture, the residue was dissolved in a minimum volume of water (10 ml) and extracted with ether (3 x 10 ml). The ethereal layer was washed with water and dried over anhydrous sodium sulfate. Evaporation gave a red solid and recrystallization from its diethyl ether solution yielded red-brown prisms of (I) after a few days.

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

In connection with synthetic and structural studies of nitro-pyridine/pyrimidine derivatives (Aznan Akhmad et al., 2010), the title compound, (I), was investigated. A small twist is evident in (I), Fig. 1, as seen in the value of the dihedral angle between the pyridyl and benzene rings of 9.89 (8) Å. The nitro group is co-planar with the pyridyl ring to which it is connected: the O1—N3—C2—C1 torsion angle is 5.0 (2)°. The observed conformation is stabilized by an intramolecular N—H···O hydrogen bond as well as a C—H···N interaction, Table 1. Overall, the molecule is close to planar with the r.m.s. deviation for all 17 non-hydrogen atoms being 0.120 Å.

In the crystal structure, centrosymmetrically related molecules are connected into dimeric aggregates via C—H···O interactions, Table 1. These are connected into a supramolecular tape along the b axis by π–π interactions between translationally related pyridyl rings and between translationally related benzene rings with the centroid···centroid separation corresponding to the length of the b axis, i.e. 3.8032 (4) Å, Fig. 2. The columns are connected by weak C—H···Cl [closest contact: C5—H5···Cl1i = 3.97 Å, C5···Cl1i = 3.6112 (19) Å and angle at H5 = 124° for i: 1/2 - x, 3/2 - y, 1 - z] and Cl···Cl [Cl1···Cl1ii = 3.4366 (7) Å for ii: 1/2 - x, -1/2 + y, 1/2 - z] contacts. A view of the unit-cell contents is given in Fig. 3.

For the structure of a related pyrimidine 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. Supramolecular tape along the b axis in (I) sustained by C—H···O and π–π interactions shown as orange and purple dashed lines, respectively.
[Figure 3] Fig. 3. Unit-cell contents for (I) shown in projection down the b axis. The C—H···O interactions are shown as orange dashed lines.
N-(4-Chlorophenyl)-3-nitropyridin-2-amine top
Crystal data top
C11H8ClN3O2F(000) = 1024
Mr = 249.65Dx = 1.605 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2586 reflections
a = 30.472 (3) Åθ = 2.3–28.0°
b = 3.8032 (4) ŵ = 0.36 mm−1
c = 21.300 (2) ÅT = 100 K
β = 123.153 (1)°Prism, red-brown
V = 2066.7 (4) Å30.40 × 0.15 × 0.05 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer		2347 independent reflections
Radiation source: fine-focus sealed tube1912 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −36→38
Tmin = 0.869, Tmax = 0.982k = −4→4
8919 measured reflectionsl = −27→27
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0483P)2 + 1.1995P]
where P = (Fo2 + 2Fc2)/3
2347 reflections(Δ/σ)max = 0.001
158 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C11H8ClN3O2V = 2066.7 (4) Å3
Mr = 249.65Z = 8
Monoclinic, C2/cMo Kα radiation
a = 30.472 (3) ŵ = 0.36 mm−1
b = 3.8032 (4) ÅT = 100 K
c = 21.300 (2) Å0.40 × 0.15 × 0.05 mm
β = 123.153 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2347 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1912 reflections with I > 2σ(I)
Tmin = 0.869, Tmax = 0.982Rint = 0.042
8919 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.33 e Å−3
2347 reflectionsΔρmin = −0.22 e Å−3
158 parameters
Special details top

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Cl10.223442 (15)0.15167 (11)0.28841 (2)0.01760 (13)
O10.00287 (5)1.1095 (3)0.32850 (6)0.0239 (3)
O2−0.01657 (5)1.3711 (4)0.40019 (7)0.0271 (3)
N10.09477 (5)0.8069 (4)0.38672 (8)0.0151 (3)
H1n0.0640 (8)0.866 (5)0.3481 (11)0.021 (5)*
N20.14771 (5)0.8205 (4)0.51652 (7)0.0155 (3)
N30.01356 (5)1.1930 (4)0.39171 (8)0.0180 (3)
C10.10203 (6)0.9037 (4)0.45291 (9)0.0141 (3)
C20.06265 (6)1.0832 (4)0.45711 (9)0.0148 (3)
C30.07133 (7)1.1672 (4)0.52649 (9)0.0175 (3)
H30.04521.28590.52960.021*
C40.11814 (7)1.0768 (4)0.59046 (9)0.0181 (4)
H40.12521.12990.63880.022*
C50.15475 (6)0.9047 (4)0.58188 (9)0.0172 (3)
H50.18720.84270.62610.021*
C60.12870 (6)0.6443 (4)0.36965 (9)0.0137 (3)
C70.18163 (6)0.5712 (4)0.42051 (9)0.0161 (3)
H70.19780.62490.47220.019*
C80.21055 (6)0.4195 (4)0.39510 (9)0.0163 (3)
H80.24670.37080.42940.020*
C90.18699 (6)0.3393 (4)0.32026 (9)0.0149 (3)
C100.13421 (6)0.4065 (4)0.26931 (9)0.0161 (3)
H100.11810.34780.21790.019*
C110.10550 (6)0.5593 (4)0.29426 (9)0.0158 (3)
H110.06940.60760.25960.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0176 (2)0.0184 (2)0.0213 (2)0.00078 (16)0.01348 (17)−0.00104 (16)
O10.0167 (6)0.0340 (8)0.0164 (6)0.0051 (5)0.0062 (5)−0.0024 (5)
O20.0182 (6)0.0350 (8)0.0279 (7)0.0118 (6)0.0125 (5)−0.0006 (6)
N10.0103 (7)0.0182 (7)0.0148 (6)0.0020 (6)0.0056 (6)−0.0004 (6)
N20.0130 (7)0.0168 (7)0.0157 (6)0.0005 (6)0.0071 (6)0.0011 (5)
N30.0148 (7)0.0186 (7)0.0213 (7)0.0018 (6)0.0103 (6)−0.0002 (6)
C10.0148 (8)0.0107 (8)0.0176 (7)−0.0025 (6)0.0094 (6)−0.0004 (6)
C20.0115 (8)0.0141 (8)0.0184 (8)−0.0007 (6)0.0079 (6)−0.0003 (6)
C30.0197 (8)0.0143 (8)0.0234 (8)0.0004 (7)0.0148 (7)0.0006 (6)
C40.0225 (9)0.0167 (8)0.0178 (8)−0.0018 (7)0.0128 (7)−0.0008 (6)
C50.0157 (8)0.0178 (9)0.0161 (7)−0.0009 (7)0.0073 (6)0.0013 (6)
C60.0145 (8)0.0104 (8)0.0178 (7)−0.0013 (6)0.0098 (6)0.0000 (6)
C70.0157 (8)0.0170 (8)0.0152 (7)−0.0004 (7)0.0082 (7)−0.0016 (6)
C80.0115 (8)0.0174 (8)0.0183 (8)0.0000 (6)0.0070 (6)−0.0001 (6)
C90.0168 (8)0.0114 (8)0.0206 (8)0.0000 (6)0.0129 (7)0.0004 (6)
C100.0163 (8)0.0158 (8)0.0149 (7)−0.0015 (6)0.0078 (6)−0.0006 (6)
C110.0129 (8)0.0148 (8)0.0169 (7)−0.0004 (6)0.0065 (6)0.0003 (6)
Geometric parameters (Å, º) top
Cl1—C91.7400 (16)C4—C51.389 (2)
O1—N31.2408 (18)C4—H40.9500
O2—N31.2312 (18)C5—H50.9500
N1—C11.353 (2)C6—C111.393 (2)
N1—C61.412 (2)C6—C71.393 (2)
N1—H1n0.87 (2)C7—C81.387 (2)
N2—C51.327 (2)C7—H70.9500
N2—C11.346 (2)C8—C91.378 (2)
N3—C21.440 (2)C8—H80.9500
C1—C21.426 (2)C9—C101.386 (2)
C2—C31.389 (2)C10—C111.376 (2)
C3—C41.372 (2)C10—H100.9500
C3—H30.9500C11—H110.9500
C1—N1—C6131.43 (14)N2—C5—H5117.6
C1—N1—H1n113.1 (12)C4—C5—H5117.6
C6—N1—H1n115.4 (12)C11—C6—C7119.45 (15)
C5—N2—C1118.99 (14)C11—C6—N1114.64 (14)
O2—N3—O1121.71 (14)C7—C6—N1125.90 (14)
O2—N3—C2118.75 (13)C8—C7—C6119.47 (14)
O1—N3—C2119.54 (13)C8—C7—H7120.3
N2—C1—N1118.36 (14)C6—C7—H7120.3
N2—C1—C2119.48 (14)C9—C8—C7120.22 (15)
N1—C1—C2122.15 (14)C9—C8—H8119.9
C3—C2—C1120.01 (15)C7—C8—H8119.9
C3—C2—N3117.09 (14)C8—C9—C10120.84 (15)
C1—C2—N3122.88 (14)C8—C9—Cl1120.15 (13)
C4—C3—C2119.25 (15)C10—C9—Cl1119.02 (12)
C4—C3—H3120.4C11—C10—C9119.08 (15)
C2—C3—H3120.4C11—C10—H10120.5
C3—C4—C5117.45 (15)C9—C10—H10120.5
C3—C4—H4121.3C10—C11—C6120.93 (15)
C5—C4—H4121.3C10—C11—H11119.5
N2—C5—C4124.83 (15)C6—C11—H11119.5
C5—N2—C1—N1−178.05 (15)C1—N2—C5—C4−0.2 (3)
C5—N2—C1—C20.7 (2)C3—C4—C5—N2−0.2 (3)
C6—N1—C1—N2−4.5 (3)C1—N1—C6—C11175.03 (16)
C6—N1—C1—C2176.74 (16)C1—N1—C6—C7−6.0 (3)
N2—C1—C2—C3−0.7 (2)C11—C6—C7—C80.9 (2)
N1—C1—C2—C3177.97 (16)N1—C6—C7—C8−178.01 (15)
N2—C1—C2—N3177.63 (14)C6—C7—C8—C9−0.5 (3)
N1—C1—C2—N3−3.7 (3)C7—C8—C9—C10−0.3 (3)
O2—N3—C2—C34.2 (2)C7—C8—C9—Cl1179.57 (13)
O1—N3—C2—C3−176.53 (15)C8—C9—C10—C110.8 (2)
O2—N3—C2—C1−174.27 (15)Cl1—C9—C10—C11−179.10 (13)
O1—N3—C2—C15.0 (2)C9—C10—C11—C6−0.4 (3)
C1—C2—C3—C40.3 (3)C7—C6—C11—C10−0.4 (2)
N3—C2—C3—C4−178.19 (15)N1—C6—C11—C10178.60 (15)
C2—C3—C4—C50.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.87 (2)1.91 (2)2.6280 (18)138.2 (17)
C7—H7···N20.952.312.909 (2)120
C3—H3···O2i0.952.483.340 (3)152
Symmetry code: (i) −x, −y+3, −z+1.

Experimental details

Crystal data
Chemical formulaC11H8ClN3O2
Mr249.65
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)30.472 (3), 3.8032 (4), 21.300 (2)
β (°) 123.153 (1)
V (Å3)2066.7 (4)
Z8
Radiation typeMo Kα
µ (mm−1)0.36
Crystal size (mm)0.40 × 0.15 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.869, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections		8919, 2347, 1912
Rint0.042
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.00
No. of reflections2347
No. of parameters158
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.22

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
D—H···AD—HH···AD···AD—H···A
N1—H1n···O10.87 (2)1.91 (2)2.6280 (18)138.2 (17)
C7—H7···N20.952.312.909 (2)120
C3—H3···O2i0.952.483.340 (3)152
Symmetry code: (i) −x, −y+3, −z+1.
 

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

First citationAznan Akhmad, M. A., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2400.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3176
https://doi.org/10.1107/S1600536811045570
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