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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Aug 20;64(Pt 9):o1800. doi: 10.1107/S1600536808026317

2-(4-Chloro­anilino)pyridine

M Zainal Abidin Fairuz a, Zaharah Aiyub a, Zanariah Abdullah a, Seik Weng Ng a,*
PMCID: PMC2960521  PMID: 21201779

Abstract

The two aromatic rings of each of the four independent molecules in the asymmetric unit of the title compound, C11H9ClN2, are approximately coplanar; the four mol­ecules are arranged into two amino–pyridyl N—H⋯N hydrogen-bonded pairs. The structure has a 15% twin component related by a twofold rotation about [100].

Related literature

The title compound exhibits fluorescence; see: Abdullah (2005 ▶); Kawai et al. (2001 ▶); Mohd Salleh et al. (2007 ▶). For the use of PLATON in the preparation of the diffraction data, see: Spek (2003 ▶).graphic file with name e-64-o1800-scheme1.jpg

Experimental

Crystal data

  • C11H9ClN2

  • M r = 204.65

  • Triclinic, Inline graphic

  • a = 7.3926 (3) Å

  • b = 15.3577 (5) Å

  • c = 17.6093 (6) Å

  • α = 73.723 (2)°

  • β = 87.360 (3)°

  • γ = 87.128 (3)°

  • V = 1915.6 (1) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.35 mm−1

  • T = 100 (2) K

  • 0.26 × 0.16 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 0.989

  • 14371 measured reflections

  • 6679 independent reflections

  • 4259 reflections with I > 2σ(I)

  • R int = 0.068

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073

  • wR(F 2) = 0.201

  • S = 1.04

  • 6679 reflections

  • 506 parameters

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026317/pk2115sup1.cif

e-64-o1800-sup1.cif (28.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026317/pk2115Isup2.hkl

e-64-o1800-Isup2.hkl (326.8KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2n⋯N3 0.88 2.19 3.019 (5) 156
N4—H4n⋯N1 0.88 2.17 3.010 (5) 160
N6—H6n⋯N7 0.88 2.13 2.968 (5) 158
N8—H8n⋯N5 0.88 2.25 3.096 (5) 161
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Acknowledgments

We thank Dr Sean Parkin of the University of Kentucky for discussion of the twinning problem, and we thank the University of Malaya for supporting this study (grant No. FS358/2008 A).

supplementary crystallographic information

Comment

The class of compounds represented by the title compound (Scheme I, Fig. 1) exhibit fluorescence (Abdullah, 2005; Kawai et al., 2001; Mohd Salleh et al., 2007). The compound crystallizes with four indepedent molecules; in each molecule, the two aromatic rings are approximately coplanar. The four molecules are arranged into two H–Hamino–Npyridyl hydrogen-bonded pairs.

Experimental

2-Chloropyridine (0.5 ml, 5.28 mmol) and 4-chloroaniline (0.67 g, 5.28 mmol) were heated for 5 h. The mixture was cooled and extracted with ether (3 x 100 ml). The ether extract was washed with water and then dried over sodium sulfate. Evaporation of the solvent gave a purple colored powder. Recrystallization from chloroform yielded colorless prisms.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement using the riding model approximation, with U(H) fixed at 1.2U(C). The amino H-atoms were similarly treated as riding (N–H 0.88 Å).

The structure initially refined to a rather high R index of 8.26%, and the difference Fourier map showed relatively large peaks for an all-light atom structure, although none were larger than 1 e Å-3. A preliminary check with the TwinRotMat routine of PLATON (Spek, 2003) showed strong evidence twofold twinning about [1 0 0]. Refinement against the TwinRotMat-generated data gave a lower R index of 7.26% along with a considerably flatter final difference Fourier map (no peak larger than ca 0.5 e Å-3). According to TwinRotMat, twinning should cause split reflections on the (n,k,l) layers with n = +/-1,2,3,4 although on some of these (e.g., n =+/- 1,4) the spot splitting was marginal. With n = -5,0,5 and on all (h,n,l) and (h,k,n) layers, the overlap was essentially perfect.

On the other hand, the reciprocal lattice diffraction data, when examined with the proprietary RLATT (Bruker, 2007) did not show any evidence of split reflections, most likely because the twin component is small.

Figures

Fig. 1.

Fig. 1.

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Thermal ellipsoid plot (Barbour, 2001) of the two pairs of hydrogen-bonded C11H9N2Cl molecules.

Crystal data

C11H9ClN2 Z = 8
Mr = 204.65 F000 = 848
Triclinic, P1 Dx = 1.419 Mg m−3
Hall symbol: -P 1 Mo Kα radiation λ = 0.71073 Å
a = 7.3926 (3) Å Cell parameters from 1607 reflections
b = 15.3577 (5) Å θ = 2.7–22.1º
c = 17.6093 (6) Å µ = 0.36 mm−1
α = 73.723 (2)º T = 100 (2) K
β = 87.360 (3)º Plate, colorless
γ = 87.128 (3)º 0.26 × 0.16 × 0.03 mm
V = 1915.6 (1) Å3
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Data collection

Bruker SMART APEX diffractometer 6679 independent reflections
Radiation source: fine-focus sealed tube 4259 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.068
T = 100(2) K θmax = 25.0º
ω scans θmin = 1.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996) h = −8→8
Tmin = 0.913, Tmax = 0.989 k = −18→18
14371 measured reflections l = −20→20
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073 H-atom parameters constrained
wR(F2) = 0.201   w = 1/[σ2(Fo2) + (0.0956P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04 (Δ/σ)max = 0.001
6679 reflections Δρmax = 0.52 e Å−3
506 parameters Δρmin = −0.52 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Cl1 0.63490 (18) 0.33288 (8) 0.13449 (6) 0.0313 (3)
Cl2 0.86940 (19) 0.47050 (8) 0.93970 (7) 0.0348 (4)
Cl3 0.85771 (18) 0.82618 (8) 0.64005 (7) 0.0323 (3)
Cl4 0.68780 (19) 0.97391 (8) 1.44898 (7) 0.0344 (4)
N1 0.7638 (5) 0.2816 (2) 0.6012 (2) 0.0235 (9)
N2 0.7050 (5) 0.3289 (2) 0.4689 (2) 0.0241 (9)
H2N 0.6767 0.3812 0.4785 0.029*
N3 0.7168 (6) 0.5220 (2) 0.4778 (2) 0.0274 (10)
N4 0.8145 (6) 0.4735 (2) 0.6050 (2) 0.0266 (10)
H4N 0.8259 0.4192 0.5975 0.032*
N5 0.6763 (5) 0.7791 (2) 1.1073 (2) 0.0242 (9)
N6 0.7641 (5) 0.8237 (2) 0.97657 (19) 0.0232 (9)
H6N 0.7937 0.8742 0.9864 0.028*
N7 0.7819 (6) 1.0150 (2) 0.9807 (2) 0.0264 (10)
N8 0.6946 (6) 0.9785 (2) 1.1120 (2) 0.0253 (10)
H8N 0.6648 0.9263 1.1056 0.030*
C1 0.7593 (6) 0.2583 (3) 0.5324 (2) 0.0198 (10)
C2 0.8080 (6) 0.1703 (3) 0.5277 (3) 0.0231 (11)
H2 0.8022 0.1552 0.4792 0.028*
C3 0.8645 (7) 0.1062 (3) 0.5954 (3) 0.0268 (11)
H3 0.8996 0.0465 0.5934 0.032*
C4 0.8702 (7) 0.1288 (3) 0.6660 (3) 0.0256 (11)
H4 0.9076 0.0854 0.7131 0.031*
C5 0.8195 (7) 0.2166 (3) 0.6653 (3) 0.0241 (11)
H5 0.8244 0.2324 0.7136 0.029*
C6 0.6904 (7) 0.3257 (3) 0.3904 (2) 0.0234 (11)
C7 0.6014 (6) 0.2570 (3) 0.3717 (3) 0.0224 (11)
H7 0.5506 0.2092 0.4126 0.027*
C8 0.5873 (6) 0.2588 (3) 0.2926 (3) 0.0243 (11)
H8 0.5312 0.2108 0.2795 0.029*
C9 0.6547 (6) 0.3301 (3) 0.2336 (2) 0.0221 (11)
C10 0.7396 (6) 0.4008 (3) 0.2509 (2) 0.0219 (11)
H10 0.7847 0.4500 0.2098 0.026*
C11 0.7564 (7) 0.3970 (3) 0.3299 (2) 0.0236 (11)
H11 0.8145 0.4445 0.3428 0.028*
C12 0.7827 (6) 0.5452 (3) 0.5387 (2) 0.0225 (11)
C13 0.8204 (6) 0.6354 (3) 0.5341 (3) 0.0242 (11)
H13 0.8699 0.6502 0.5775 0.029*
C14 0.7839 (6) 0.7019 (3) 0.4651 (2) 0.0250 (11)
H14 0.8077 0.7635 0.4604 0.030*
C15 0.7119 (7) 0.6780 (3) 0.4026 (3) 0.0284 (12)
H15 0.6839 0.7228 0.3547 0.034*
C16 0.6823 (7) 0.5882 (3) 0.4117 (3) 0.0267 (11)
H16 0.6345 0.5720 0.3685 0.032*
C17 0.8306 (6) 0.4777 (3) 0.6828 (2) 0.0197 (10)
C18 0.7407 (6) 0.5441 (3) 0.7125 (2) 0.0225 (11)
H18 0.6689 0.5906 0.6785 0.027*
C19 0.7548 (6) 0.5429 (3) 0.7910 (2) 0.0234 (11)
H19 0.6954 0.5889 0.8105 0.028*
C20 0.8569 (6) 0.4734 (3) 0.8409 (2) 0.0232 (11)
C21 0.9467 (6) 0.4064 (3) 0.8133 (2) 0.0235 (11)
H21 1.0167 0.3594 0.8477 0.028*
C22 0.9327 (7) 0.4092 (3) 0.7348 (3) 0.0242 (11)
H22 0.9938 0.3634 0.7155 0.029*
C23 0.6090 (7) 0.7168 (3) 1.1698 (3) 0.0258 (11)
H23 0.5938 0.7324 1.2183 0.031*
C24 0.5600 (7) 0.6317 (3) 1.1694 (3) 0.0270 (12)
H24 0.5098 0.5904 1.2154 0.032*
C25 0.5872 (7) 0.6088 (3) 1.0989 (2) 0.0259 (12)
H25 0.5581 0.5502 1.0963 0.031*
C26 0.6557 (7) 0.6702 (3) 1.0330 (3) 0.0257 (11)
H26 0.6731 0.6554 0.9843 0.031*
C27 0.7002 (6) 0.7565 (3) 1.0396 (2) 0.0230 (11)
C28 0.7872 (6) 0.8202 (3) 0.8975 (2) 0.0179 (10)
C29 0.8870 (6) 0.7517 (3) 0.8758 (3) 0.0235 (11)
H29 0.9420 0.7036 0.9153 0.028*
C30 0.9073 (6) 0.7526 (3) 0.7969 (3) 0.0252 (11)
H30 0.9730 0.7047 0.7823 0.030*
C31 0.8304 (6) 0.8243 (3) 0.7398 (2) 0.0221 (11)
C32 0.7343 (6) 0.8940 (3) 0.7592 (2) 0.0212 (11)
H32 0.6846 0.9432 0.7190 0.025*
C33 0.7101 (6) 0.8919 (3) 0.8391 (2) 0.0203 (10)
H33 0.6414 0.9391 0.8535 0.024*
C34 0.8266 (7) 1.0766 (3) 0.9131 (3) 0.0280 (12)
H34 0.8587 1.0553 0.8684 0.034*
C35 0.8294 (7) 1.1685 (3) 0.9036 (3) 0.0276 (12)
H35 0.8688 1.2092 0.8550 0.033*
C36 0.7723 (7) 1.1994 (3) 0.9681 (3) 0.0307 (12)
H36 0.7666 1.2626 0.9637 0.037*
C37 0.7243 (6) 1.1380 (3) 1.0383 (3) 0.0251 (11)
H37 0.6846 1.1580 1.0829 0.030*
C38 0.7346 (7) 1.0458 (3) 1.0431 (2) 0.0239 (11)
C39 0.6953 (6) 0.9824 (3) 1.1897 (2) 0.0213 (10)
C40 0.7925 (7) 1.0447 (3) 1.2151 (2) 0.0240 (11)
H40 0.8622 1.0883 1.1778 0.029*
C41 0.7873 (6) 1.0427 (3) 1.2940 (3) 0.0248 (11)
H41 0.8508 1.0860 1.3107 0.030*
C42 0.6890 (6) 0.9773 (3) 1.3491 (3) 0.0239 (11)
C43 0.5945 (7) 0.9148 (3) 1.3258 (2) 0.0234 (11)
H43 0.5293 0.8697 1.3637 0.028*
C44 0.5958 (6) 0.9185 (3) 1.2462 (2) 0.0230 (11)
H44 0.5275 0.8767 1.2298 0.028*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl1 0.0369 (8) 0.0382 (7) 0.0208 (6) 0.0045 (6) −0.0054 (5) −0.0120 (5)
Cl2 0.0479 (9) 0.0381 (7) 0.0209 (6) 0.0003 (6) −0.0111 (6) −0.0113 (5)
Cl3 0.0375 (8) 0.0411 (7) 0.0217 (6) −0.0116 (6) 0.0039 (5) −0.0132 (5)
Cl4 0.0421 (9) 0.0412 (7) 0.0214 (6) −0.0039 (6) 0.0045 (6) −0.0114 (5)
N1 0.026 (2) 0.0204 (19) 0.022 (2) −0.0022 (17) −0.0010 (17) −0.0023 (16)
N2 0.040 (3) 0.0166 (18) 0.0154 (19) −0.0009 (18) −0.0052 (17) −0.0041 (15)
N3 0.038 (3) 0.022 (2) 0.020 (2) 0.0031 (19) −0.0047 (18) −0.0027 (16)
N4 0.043 (3) 0.0176 (19) 0.0169 (19) 0.0005 (19) −0.0004 (18) −0.0021 (15)
N5 0.028 (2) 0.0214 (19) 0.021 (2) −0.0015 (18) −0.0023 (17) −0.0025 (16)
N6 0.034 (3) 0.0211 (19) 0.0137 (18) −0.0044 (18) 0.0002 (17) −0.0037 (15)
N7 0.039 (3) 0.023 (2) 0.017 (2) −0.0059 (19) −0.0035 (18) −0.0050 (16)
N8 0.042 (3) 0.0178 (19) 0.0151 (19) −0.0064 (18) −0.0036 (17) −0.0014 (15)
C1 0.021 (3) 0.021 (2) 0.017 (2) −0.008 (2) −0.0024 (19) −0.0021 (18)
C2 0.028 (3) 0.025 (2) 0.017 (2) −0.004 (2) 0.000 (2) −0.0063 (19)
C3 0.027 (3) 0.021 (2) 0.030 (3) 0.000 (2) −0.001 (2) −0.002 (2)
C4 0.030 (3) 0.023 (2) 0.021 (2) −0.004 (2) −0.005 (2) 0.0004 (19)
C5 0.032 (3) 0.021 (2) 0.017 (2) −0.004 (2) −0.006 (2) 0.0001 (18)
C6 0.031 (3) 0.020 (2) 0.019 (2) 0.000 (2) −0.007 (2) −0.0049 (19)
C7 0.020 (3) 0.022 (2) 0.025 (2) −0.002 (2) −0.002 (2) −0.0064 (19)
C8 0.024 (3) 0.020 (2) 0.032 (3) 0.004 (2) −0.007 (2) −0.012 (2)
C9 0.024 (3) 0.023 (2) 0.020 (2) 0.003 (2) −0.005 (2) −0.0074 (18)
C10 0.025 (3) 0.019 (2) 0.020 (2) 0.001 (2) −0.002 (2) −0.0016 (18)
C11 0.032 (3) 0.019 (2) 0.019 (2) −0.003 (2) −0.003 (2) −0.0032 (18)
C12 0.026 (3) 0.025 (2) 0.016 (2) −0.004 (2) 0.003 (2) −0.0036 (18)
C13 0.028 (3) 0.022 (2) 0.021 (2) 0.000 (2) 0.000 (2) −0.0029 (19)
C14 0.028 (3) 0.022 (2) 0.023 (2) −0.004 (2) −0.001 (2) −0.0031 (19)
C15 0.038 (3) 0.024 (2) 0.018 (2) 0.007 (2) −0.002 (2) 0.0020 (19)
C16 0.032 (3) 0.027 (3) 0.022 (2) 0.003 (2) −0.007 (2) −0.008 (2)
C17 0.027 (3) 0.014 (2) 0.017 (2) −0.003 (2) 0.002 (2) −0.0027 (17)
C18 0.026 (3) 0.020 (2) 0.021 (2) −0.003 (2) −0.003 (2) −0.0026 (18)
C19 0.023 (3) 0.022 (2) 0.025 (2) −0.005 (2) 0.001 (2) −0.0060 (19)
C20 0.024 (3) 0.025 (2) 0.019 (2) −0.011 (2) −0.001 (2) −0.0030 (19)
C21 0.027 (3) 0.022 (2) 0.020 (2) −0.003 (2) −0.005 (2) −0.0028 (19)
C22 0.032 (3) 0.013 (2) 0.025 (2) −0.001 (2) 0.000 (2) −0.0026 (18)
C23 0.037 (3) 0.020 (2) 0.018 (2) 0.000 (2) 0.000 (2) −0.0022 (19)
C24 0.034 (3) 0.021 (2) 0.021 (2) −0.003 (2) 0.001 (2) 0.0028 (19)
C25 0.031 (3) 0.021 (2) 0.025 (3) −0.006 (2) −0.008 (2) −0.0032 (19)
C26 0.033 (3) 0.020 (2) 0.022 (2) 0.001 (2) −0.006 (2) −0.0027 (19)
C27 0.026 (3) 0.023 (2) 0.018 (2) −0.001 (2) −0.007 (2) −0.0010 (19)
C28 0.020 (3) 0.019 (2) 0.016 (2) −0.0062 (19) 0.0003 (19) −0.0056 (17)
C29 0.024 (3) 0.019 (2) 0.027 (2) −0.001 (2) −0.003 (2) −0.0050 (19)
C30 0.024 (3) 0.027 (2) 0.027 (3) −0.003 (2) 0.004 (2) −0.011 (2)
C31 0.027 (3) 0.025 (2) 0.015 (2) −0.008 (2) 0.004 (2) −0.0062 (18)
C32 0.025 (3) 0.021 (2) 0.017 (2) −0.005 (2) −0.0010 (19) −0.0025 (18)
C33 0.020 (3) 0.017 (2) 0.023 (2) −0.0011 (19) 0.000 (2) −0.0051 (18)
C34 0.040 (3) 0.024 (2) 0.019 (2) −0.005 (2) −0.004 (2) −0.0048 (19)
C35 0.038 (3) 0.025 (2) 0.015 (2) −0.004 (2) −0.005 (2) 0.0011 (19)
C36 0.039 (3) 0.023 (2) 0.028 (3) −0.003 (2) −0.010 (2) −0.001 (2)
C37 0.027 (3) 0.026 (2) 0.020 (2) −0.001 (2) −0.005 (2) −0.0006 (19)
C38 0.029 (3) 0.023 (2) 0.017 (2) −0.003 (2) −0.004 (2) −0.0005 (19)
C39 0.025 (3) 0.018 (2) 0.018 (2) 0.004 (2) −0.003 (2) −0.0002 (18)
C40 0.028 (3) 0.020 (2) 0.022 (2) −0.003 (2) −0.003 (2) −0.0026 (19)
C41 0.021 (3) 0.025 (2) 0.025 (3) −0.002 (2) 0.000 (2) −0.002 (2)
C42 0.023 (3) 0.026 (2) 0.020 (2) 0.006 (2) 0.001 (2) −0.0024 (19)
C43 0.028 (3) 0.020 (2) 0.020 (2) −0.004 (2) 0.005 (2) −0.0034 (19)
C44 0.027 (3) 0.019 (2) 0.022 (2) −0.005 (2) −0.004 (2) −0.0028 (18)
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Geometric parameters (Å, °)

Cl1—C9 1.747 (4) C15—H15 0.9500
Cl2—C20 1.734 (4) C16—H16 0.9500
Cl3—C31 1.751 (4) C17—C18 1.397 (6)
Cl4—C42 1.744 (5) C17—C22 1.400 (6)
N1—C5 1.345 (5) C18—C19 1.385 (6)
N1—C1 1.359 (5) C18—H18 0.9500
N2—C1 1.380 (5) C19—C20 1.391 (6)
N2—C6 1.406 (5) C19—H19 0.9500
N2—H2N 0.8800 C20—C21 1.386 (7)
N3—C16 1.338 (5) C21—C22 1.378 (6)
N3—C12 1.340 (6) C21—H21 0.9500
N4—C12 1.381 (5) C22—H22 0.9500
N4—C17 1.401 (5) C23—C24 1.376 (6)
N4—H4N 0.8800 C23—H23 0.9500
N5—C27 1.334 (6) C24—C25 1.385 (6)
N5—C23 1.335 (5) C24—H24 0.9500
N6—C27 1.370 (5) C25—C26 1.368 (6)
N6—C28 1.411 (5) C25—H25 0.9500
N6—H6N 0.8800 C26—C27 1.419 (6)
N7—C34 1.336 (5) C26—H26 0.9500
N7—C38 1.340 (6) C28—C29 1.385 (6)
N8—C39 1.386 (5) C28—C33 1.397 (6)
N8—C38 1.387 (5) C29—C30 1.387 (6)
N8—H8N 0.8800 C29—H29 0.9500
C1—C2 1.405 (6) C30—C31 1.385 (6)
C2—C3 1.382 (6) C30—H30 0.9500
C2—H2 0.9500 C31—C32 1.369 (6)
C3—C4 1.384 (6) C32—C33 1.401 (6)
C3—H3 0.9500 C32—H32 0.9500
C4—C5 1.378 (6) C33—H33 0.9500
C4—H4 0.9500 C34—C35 1.376 (6)
C5—H5 0.9500 C34—H34 0.9500
C6—C11 1.387 (5) C35—C36 1.389 (7)
C6—C7 1.393 (6) C35—H35 0.9500
C7—C8 1.394 (6) C36—C37 1.373 (6)
C7—H7 0.9500 C36—H36 0.9500
C8—C9 1.377 (6) C37—C38 1.392 (6)
C8—H8 0.9500 C37—H37 0.9500
C9—C10 1.391 (6) C39—C44 1.397 (6)
C10—C11 1.387 (6) C39—C40 1.403 (6)
C10—H10 0.9500 C40—C41 1.381 (6)
C11—H11 0.9500 C40—H40 0.9500
C12—C13 1.406 (6) C41—C42 1.393 (6)
C13—C14 1.377 (6) C41—H41 0.9500
C13—H13 0.9500 C42—C43 1.376 (6)
C14—C15 1.390 (6) C43—C44 1.386 (6)
C14—H14 0.9500 C43—H43 0.9500
C15—C16 1.371 (6) C44—H44 0.9500
C5—N1—C1 117.0 (4) C21—C20—Cl2 119.7 (3)
C1—N2—C6 126.6 (4) C19—C20—Cl2 119.1 (4)
C1—N2—H2N 116.7 C22—C21—C20 118.7 (4)
C6—N2—H2N 116.7 C22—C21—H21 120.6
C16—N3—C12 117.9 (4) C20—C21—H21 120.6
C12—N4—C17 127.2 (4) C21—C22—C17 121.8 (5)
C12—N4—H4N 116.4 C21—C22—H22 119.1
C17—N4—H4N 116.4 C17—C22—H22 119.1
C27—N5—C23 117.4 (4) N5—C23—C24 125.0 (4)
C27—N6—C28 126.6 (4) N5—C23—H23 117.5
C27—N6—H6N 116.7 C24—C23—H23 117.5
C28—N6—H6N 116.7 C23—C24—C25 117.0 (4)
C34—N7—C38 117.1 (4) C23—C24—H24 121.5
C39—N8—C38 128.7 (4) C25—C24—H24 121.5
C39—N8—H8N 115.7 C26—C25—C24 120.4 (4)
C38—N8—H8N 115.7 C26—C25—H25 119.8
N1—C1—N2 113.7 (4) C24—C25—H25 119.8
N1—C1—C2 122.1 (4) C25—C26—C27 118.2 (4)
N2—C1—C2 124.2 (4) C25—C26—H26 120.9
C3—C2—C1 118.5 (4) C27—C26—H26 120.9
C3—C2—H2 120.7 N5—C27—N6 115.1 (4)
C1—C2—H2 120.7 N5—C27—C26 122.1 (4)
C2—C3—C4 120.2 (4) N6—C27—C26 122.7 (4)
C2—C3—H3 119.9 C29—C28—C33 119.6 (4)
C4—C3—H3 119.9 C29—C28—N6 123.2 (4)
C5—C4—C3 117.5 (4) C33—C28—N6 117.2 (4)
C5—C4—H4 121.2 C28—C29—C30 120.6 (4)
C3—C4—H4 121.2 C28—C29—H29 119.7
N1—C5—C4 124.7 (4) C30—C29—H29 119.7
N1—C5—H5 117.6 C31—C30—C29 119.0 (5)
C4—C5—H5 117.6 C31—C30—H30 120.5
C11—C6—C7 119.4 (4) C29—C30—H30 120.5
C11—C6—N2 118.3 (4) C32—C31—C30 121.8 (4)
C7—C6—N2 122.1 (4) C32—C31—Cl3 119.1 (3)
C6—C7—C8 119.5 (4) C30—C31—Cl3 119.1 (4)
C6—C7—H7 120.3 C31—C32—C33 119.2 (4)
C8—C7—H7 120.3 C31—C32—H32 120.4
C9—C8—C7 120.0 (4) C33—C32—H32 120.4
C9—C8—H8 120.0 C28—C33—C32 119.9 (4)
C7—C8—H8 120.0 C28—C33—H33 120.1
C8—C9—C10 121.5 (4) C32—C33—H33 120.1
C8—C9—Cl1 119.9 (3) N7—C34—C35 124.7 (5)
C10—C9—Cl1 118.6 (3) N7—C34—H34 117.6
C11—C10—C9 117.9 (4) C35—C34—H34 117.6
C11—C10—H10 121.0 C34—C35—C36 117.2 (4)
C9—C10—H10 121.0 C34—C35—H35 121.4
C10—C11—C6 121.7 (4) C36—C35—H35 121.4
C10—C11—H11 119.2 C37—C36—C35 119.5 (4)
C6—C11—H11 119.2 C37—C36—H36 120.2
N3—C12—N4 114.8 (4) C35—C36—H36 120.2
N3—C12—C13 122.1 (4) C36—C37—C38 119.0 (5)
N4—C12—C13 123.1 (4) C36—C37—H37 120.5
C14—C13—C12 118.5 (4) C38—C37—H37 120.5
C14—C13—H13 120.7 N7—C38—N8 114.3 (4)
C12—C13—H13 120.7 N7—C38—C37 122.4 (4)
C13—C14—C15 119.3 (4) N8—C38—C37 123.2 (4)
C13—C14—H14 120.4 N8—C39—C44 117.4 (4)
C15—C14—H14 120.4 N8—C39—C40 124.2 (4)
C16—C15—C14 118.3 (4) C44—C39—C40 118.3 (4)
C16—C15—H15 120.8 C41—C40—C39 120.2 (4)
C14—C15—H15 120.8 C41—C40—H40 119.9
N3—C16—C15 123.8 (4) C39—C40—H40 119.9
N3—C16—H16 118.1 C40—C41—C42 120.0 (4)
C15—C16—H16 118.1 C40—C41—H41 120.0
C18—C17—C22 118.2 (4) C42—C41—H41 120.0
C18—C17—N4 123.1 (4) C43—C42—C41 120.8 (4)
C22—C17—N4 118.6 (4) C43—C42—Cl4 119.6 (3)
C19—C18—C17 120.8 (4) C41—C42—Cl4 119.6 (4)
C19—C18—H18 119.6 C42—C43—C44 119.0 (4)
C17—C18—H18 119.6 C42—C43—H43 120.5
C18—C19—C20 119.2 (5) C44—C43—H43 120.5
C18—C19—H19 120.4 C43—C44—C39 121.6 (4)
C20—C19—H19 120.4 C43—C44—H44 119.2
C21—C20—C19 121.2 (4) C39—C44—H44 119.2
C5—N1—C1—N2 −178.5 (4) C27—N5—C23—C24 −1.1 (7)
C5—N1—C1—C2 0.8 (6) N5—C23—C24—C25 1.6 (8)
C6—N2—C1—N1 178.8 (4) C23—C24—C25—C26 −1.5 (7)
C6—N2—C1—C2 −0.5 (7) C24—C25—C26—C27 1.0 (7)
N1—C1—C2—C3 −0.9 (7) C23—N5—C27—N6 178.0 (4)
N2—C1—C2—C3 178.3 (4) C23—N5—C27—C26 0.4 (7)
C1—C2—C3—C4 0.8 (7) C28—N6—C27—N5 −174.5 (4)
C2—C3—C4—C5 −0.6 (7) C28—N6—C27—C26 3.1 (7)
C1—N1—C5—C4 −0.6 (7) C25—C26—C27—N5 −0.4 (7)
C3—C4—C5—N1 0.5 (7) C25—C26—C27—N6 −177.8 (4)
C1—N2—C6—C11 −136.0 (5) C27—N6—C28—C29 −54.0 (6)
C1—N2—C6—C7 48.5 (7) C27—N6—C28—C33 128.5 (5)
C11—C6—C7—C8 2.9 (7) C33—C28—C29—C30 −1.5 (6)
N2—C6—C7—C8 178.4 (4) N6—C28—C29—C30 −179.0 (4)
C6—C7—C8—C9 −2.6 (7) C28—C29—C30—C31 1.7 (6)
C7—C8—C9—C10 0.8 (7) C29—C30—C31—C32 −0.3 (7)
C7—C8—C9—Cl1 −179.3 (4) C29—C30—C31—Cl3 179.4 (3)
C8—C9—C10—C11 0.6 (7) C30—C31—C32—C33 −1.2 (7)
Cl1—C9—C10—C11 −179.2 (4) Cl3—C31—C32—C33 179.1 (3)
C9—C10—C11—C6 −0.3 (7) C29—C28—C33—C32 0.0 (6)
C7—C6—C11—C10 −1.5 (7) N6—C28—C33—C32 177.6 (4)
N2—C6—C11—C10 −177.1 (4) C31—C32—C33—C28 1.4 (6)
C16—N3—C12—N4 179.8 (4) C38—N7—C34—C35 0.9 (7)
C16—N3—C12—C13 −1.8 (7) N7—C34—C35—C36 −3.6 (8)
C17—N4—C12—N3 −159.7 (5) C34—C35—C36—C37 2.9 (7)
C17—N4—C12—C13 21.9 (8) C35—C36—C37—C38 0.2 (7)
N3—C12—C13—C14 1.6 (8) C34—N7—C38—N8 −178.3 (4)
N4—C12—C13—C14 179.9 (5) C34—N7—C38—C37 2.6 (7)
C12—C13—C14—C15 −0.2 (7) C39—N8—C38—N7 158.5 (5)
C13—C14—C15—C16 −1.0 (8) C39—N8—C38—C37 −22.4 (8)
C12—N3—C16—C15 0.6 (8) C36—C37—C38—N7 −3.1 (7)
C14—C15—C16—N3 0.8 (8) C36—C37—C38—N8 177.9 (5)
C12—N4—C17—C18 30.0 (7) C38—N8—C39—C44 159.5 (5)
C12—N4—C17—C22 −153.9 (4) C38—N8—C39—C40 −22.0 (8)
C22—C17—C18—C19 1.1 (6) N8—C39—C40—C41 −179.1 (5)
N4—C17—C18—C19 177.1 (4) C44—C39—C40—C41 −0.6 (7)
C17—C18—C19—C20 −1.4 (6) C39—C40—C41—C42 1.6 (7)
C18—C19—C20—C21 1.0 (6) C40—C41—C42—C43 −0.8 (7)
C18—C19—C20—Cl2 −178.3 (3) C40—C41—C42—Cl4 178.5 (4)
C19—C20—C21—C22 −0.3 (6) C41—C42—C43—C44 −1.0 (7)
Cl2—C20—C21—C22 179.0 (3) Cl4—C42—C43—C44 179.7 (4)
C20—C21—C22—C17 0.0 (7) C42—C43—C44—C39 2.1 (7)
C18—C17—C22—C21 −0.4 (6) N8—C39—C44—C43 177.3 (4)
N4—C17—C22—C21 −176.6 (4) C40—C39—C44—C43 −1.2 (7)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N2—H2n···N3 0.88 2.19 3.019 (5) 156
N4—H4n···N1 0.88 2.17 3.010 (5) 160
N6—H6n···N7 0.88 2.13 2.968 (5) 158
N8—H8n···N5 0.88 2.25 3.096 (5) 161
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2115).

References

  1. Abdullah, Z. (2005). Int. J. Chem. Sci.3, 9–15.
  2. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  3. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc.11, 23–32.
  5. Mohd Salleh, N., Ling, L. P., Abdullah, Z. M. A. A. & Aiyub, Z. (2007). Malays. J. Anal. Sci.11, 229–236.
  6. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  7. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  8. Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  9. Westrip, S. P. (2008). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026317/pk2115sup1.cif

e-64-o1800-sup1.cif (28.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026317/pk2115Isup2.hkl

e-64-o1800-Isup2.hkl (326.8KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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