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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1800.
Published online 2008 August 20. doi: 10.1107/S1600536808026317.
PMCID: PMC2960521
2-(4-Chloro­anilino)pyridine
M. Zainal Abidin Fairuz,a Zaharah Aiyub,a Zanariah Abdullah,a and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received August 13, 2008; Accepted August 14, 2008.
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[cdots, three dots, centered]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 [triangle]); Kawai et al. (2001 [triangle]); Mohd Salleh et al. (2007 [triangle]). For the use of PLATON in the preparation of the diffraction data, see: Spek (2003 [triangle]).
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Object name is e-64-o1800-scheme1.jpg Object name is e-64-o1800-scheme1.jpg
Crystal data
  • C11H9ClN2
  • M r = 204.65
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1800-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026317/pk2115sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026317/pk2115Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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.
Thermal ellipsoid plot (Barbour, 2001) of the two pairs of hydrogen-bonded C11H9N2Cl molecules.
Crystal data
C11H9ClN2Z = 8
Mr = 204.65F000 = 848
Triclinic, P1Dx = 1.419 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.3926 (3) ÅCell parameters from 1607 reflections
b = 15.3577 (5) Åθ = 2.7–22.1º
c = 17.6093 (6) ŵ = 0.36 mm1
α = 73.723 (2)ºT = 100 (2) K
β = 87.360 (3)ºPlate, colorless
γ = 87.128 (3)º0.26 × 0.16 × 0.03 mm
V = 1915.6 (1) Å3
Data collection
Bruker SMART APEX diffractometer6679 independent reflections
Radiation source: fine-focus sealed tube4259 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.068
T = 100(2) Kθmax = 25.0º
ω scansθmin = 1.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.913, Tmax = 0.989k = −18→18
14371 measured reflectionsl = −20→20
Refinement
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073H-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 reflectionsΔρmax = 0.52 e Å3
506 parametersΔρmin = −0.52 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
Cl10.63490 (18)0.33288 (8)0.13449 (6)0.0313 (3)
Cl20.86940 (19)0.47050 (8)0.93970 (7)0.0348 (4)
Cl30.85771 (18)0.82618 (8)0.64005 (7)0.0323 (3)
Cl40.68780 (19)0.97391 (8)1.44898 (7)0.0344 (4)
N10.7638 (5)0.2816 (2)0.6012 (2)0.0235 (9)
N20.7050 (5)0.3289 (2)0.4689 (2)0.0241 (9)
H2N0.67670.38120.47850.029*
N30.7168 (6)0.5220 (2)0.4778 (2)0.0274 (10)
N40.8145 (6)0.4735 (2)0.6050 (2)0.0266 (10)
H4N0.82590.41920.59750.032*
N50.6763 (5)0.7791 (2)1.1073 (2)0.0242 (9)
N60.7641 (5)0.8237 (2)0.97657 (19)0.0232 (9)
H6N0.79370.87420.98640.028*
N70.7819 (6)1.0150 (2)0.9807 (2)0.0264 (10)
N80.6946 (6)0.9785 (2)1.1120 (2)0.0253 (10)
H8N0.66480.92631.10560.030*
C10.7593 (6)0.2583 (3)0.5324 (2)0.0198 (10)
C20.8080 (6)0.1703 (3)0.5277 (3)0.0231 (11)
H20.80220.15520.47920.028*
C30.8645 (7)0.1062 (3)0.5954 (3)0.0268 (11)
H30.89960.04650.59340.032*
C40.8702 (7)0.1288 (3)0.6660 (3)0.0256 (11)
H40.90760.08540.71310.031*
C50.8195 (7)0.2166 (3)0.6653 (3)0.0241 (11)
H50.82440.23240.71360.029*
C60.6904 (7)0.3257 (3)0.3904 (2)0.0234 (11)
C70.6014 (6)0.2570 (3)0.3717 (3)0.0224 (11)
H70.55060.20920.41260.027*
C80.5873 (6)0.2588 (3)0.2926 (3)0.0243 (11)
H80.53120.21080.27950.029*
C90.6547 (6)0.3301 (3)0.2336 (2)0.0221 (11)
C100.7396 (6)0.4008 (3)0.2509 (2)0.0219 (11)
H100.78470.45000.20980.026*
C110.7564 (7)0.3970 (3)0.3299 (2)0.0236 (11)
H110.81450.44450.34280.028*
C120.7827 (6)0.5452 (3)0.5387 (2)0.0225 (11)
C130.8204 (6)0.6354 (3)0.5341 (3)0.0242 (11)
H130.86990.65020.57750.029*
C140.7839 (6)0.7019 (3)0.4651 (2)0.0250 (11)
H140.80770.76350.46040.030*
C150.7119 (7)0.6780 (3)0.4026 (3)0.0284 (12)
H150.68390.72280.35470.034*
C160.6823 (7)0.5882 (3)0.4117 (3)0.0267 (11)
H160.63450.57200.36850.032*
C170.8306 (6)0.4777 (3)0.6828 (2)0.0197 (10)
C180.7407 (6)0.5441 (3)0.7125 (2)0.0225 (11)
H180.66890.59060.67850.027*
C190.7548 (6)0.5429 (3)0.7910 (2)0.0234 (11)
H190.69540.58890.81050.028*
C200.8569 (6)0.4734 (3)0.8409 (2)0.0232 (11)
C210.9467 (6)0.4064 (3)0.8133 (2)0.0235 (11)
H211.01670.35940.84770.028*
C220.9327 (7)0.4092 (3)0.7348 (3)0.0242 (11)
H220.99380.36340.71550.029*
C230.6090 (7)0.7168 (3)1.1698 (3)0.0258 (11)
H230.59380.73241.21830.031*
C240.5600 (7)0.6317 (3)1.1694 (3)0.0270 (12)
H240.50980.59041.21540.032*
C250.5872 (7)0.6088 (3)1.0989 (2)0.0259 (12)
H250.55810.55021.09630.031*
C260.6557 (7)0.6702 (3)1.0330 (3)0.0257 (11)
H260.67310.65540.98430.031*
C270.7002 (6)0.7565 (3)1.0396 (2)0.0230 (11)
C280.7872 (6)0.8202 (3)0.8975 (2)0.0179 (10)
C290.8870 (6)0.7517 (3)0.8758 (3)0.0235 (11)
H290.94200.70360.91530.028*
C300.9073 (6)0.7526 (3)0.7969 (3)0.0252 (11)
H300.97300.70470.78230.030*
C310.8304 (6)0.8243 (3)0.7398 (2)0.0221 (11)
C320.7343 (6)0.8940 (3)0.7592 (2)0.0212 (11)
H320.68460.94320.71900.025*
C330.7101 (6)0.8919 (3)0.8391 (2)0.0203 (10)
H330.64140.93910.85350.024*
C340.8266 (7)1.0766 (3)0.9131 (3)0.0280 (12)
H340.85871.05530.86840.034*
C350.8294 (7)1.1685 (3)0.9036 (3)0.0276 (12)
H350.86881.20920.85500.033*
C360.7723 (7)1.1994 (3)0.9681 (3)0.0307 (12)
H360.76661.26260.96370.037*
C370.7243 (6)1.1380 (3)1.0383 (3)0.0251 (11)
H370.68461.15801.08290.030*
C380.7346 (7)1.0458 (3)1.0431 (2)0.0239 (11)
C390.6953 (6)0.9824 (3)1.1897 (2)0.0213 (10)
C400.7925 (7)1.0447 (3)1.2151 (2)0.0240 (11)
H400.86221.08831.17780.029*
C410.7873 (6)1.0427 (3)1.2940 (3)0.0248 (11)
H410.85081.08601.31070.030*
C420.6890 (6)0.9773 (3)1.3491 (3)0.0239 (11)
C430.5945 (7)0.9148 (3)1.3258 (2)0.0234 (11)
H430.52930.86971.36370.028*
C440.5958 (6)0.9185 (3)1.2462 (2)0.0230 (11)
H440.52750.87671.22980.028*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
Cl10.0369 (8)0.0382 (7)0.0208 (6)0.0045 (6)−0.0054 (5)−0.0120 (5)
Cl20.0479 (9)0.0381 (7)0.0209 (6)0.0003 (6)−0.0111 (6)−0.0113 (5)
Cl30.0375 (8)0.0411 (7)0.0217 (6)−0.0116 (6)0.0039 (5)−0.0132 (5)
Cl40.0421 (9)0.0412 (7)0.0214 (6)−0.0039 (6)0.0045 (6)−0.0114 (5)
N10.026 (2)0.0204 (19)0.022 (2)−0.0022 (17)−0.0010 (17)−0.0023 (16)
N20.040 (3)0.0166 (18)0.0154 (19)−0.0009 (18)−0.0052 (17)−0.0041 (15)
N30.038 (3)0.022 (2)0.020 (2)0.0031 (19)−0.0047 (18)−0.0027 (16)
N40.043 (3)0.0176 (19)0.0169 (19)0.0005 (19)−0.0004 (18)−0.0021 (15)
N50.028 (2)0.0214 (19)0.021 (2)−0.0015 (18)−0.0023 (17)−0.0025 (16)
N60.034 (3)0.0211 (19)0.0137 (18)−0.0044 (18)0.0002 (17)−0.0037 (15)
N70.039 (3)0.023 (2)0.017 (2)−0.0059 (19)−0.0035 (18)−0.0050 (16)
N80.042 (3)0.0178 (19)0.0151 (19)−0.0064 (18)−0.0036 (17)−0.0014 (15)
C10.021 (3)0.021 (2)0.017 (2)−0.008 (2)−0.0024 (19)−0.0021 (18)
C20.028 (3)0.025 (2)0.017 (2)−0.004 (2)0.000 (2)−0.0063 (19)
C30.027 (3)0.021 (2)0.030 (3)0.000 (2)−0.001 (2)−0.002 (2)
C40.030 (3)0.023 (2)0.021 (2)−0.004 (2)−0.005 (2)0.0004 (19)
C50.032 (3)0.021 (2)0.017 (2)−0.004 (2)−0.006 (2)0.0001 (18)
C60.031 (3)0.020 (2)0.019 (2)0.000 (2)−0.007 (2)−0.0049 (19)
C70.020 (3)0.022 (2)0.025 (2)−0.002 (2)−0.002 (2)−0.0064 (19)
C80.024 (3)0.020 (2)0.032 (3)0.004 (2)−0.007 (2)−0.012 (2)
C90.024 (3)0.023 (2)0.020 (2)0.003 (2)−0.005 (2)−0.0074 (18)
C100.025 (3)0.019 (2)0.020 (2)0.001 (2)−0.002 (2)−0.0016 (18)
C110.032 (3)0.019 (2)0.019 (2)−0.003 (2)−0.003 (2)−0.0032 (18)
C120.026 (3)0.025 (2)0.016 (2)−0.004 (2)0.003 (2)−0.0036 (18)
C130.028 (3)0.022 (2)0.021 (2)0.000 (2)0.000 (2)−0.0029 (19)
C140.028 (3)0.022 (2)0.023 (2)−0.004 (2)−0.001 (2)−0.0031 (19)
C150.038 (3)0.024 (2)0.018 (2)0.007 (2)−0.002 (2)0.0020 (19)
C160.032 (3)0.027 (3)0.022 (2)0.003 (2)−0.007 (2)−0.008 (2)
C170.027 (3)0.014 (2)0.017 (2)−0.003 (2)0.002 (2)−0.0027 (17)
C180.026 (3)0.020 (2)0.021 (2)−0.003 (2)−0.003 (2)−0.0026 (18)
C190.023 (3)0.022 (2)0.025 (2)−0.005 (2)0.001 (2)−0.0060 (19)
C200.024 (3)0.025 (2)0.019 (2)−0.011 (2)−0.001 (2)−0.0030 (19)
C210.027 (3)0.022 (2)0.020 (2)−0.003 (2)−0.005 (2)−0.0028 (19)
C220.032 (3)0.013 (2)0.025 (2)−0.001 (2)0.000 (2)−0.0026 (18)
C230.037 (3)0.020 (2)0.018 (2)0.000 (2)0.000 (2)−0.0022 (19)
C240.034 (3)0.021 (2)0.021 (2)−0.003 (2)0.001 (2)0.0028 (19)
C250.031 (3)0.021 (2)0.025 (3)−0.006 (2)−0.008 (2)−0.0032 (19)
C260.033 (3)0.020 (2)0.022 (2)0.001 (2)−0.006 (2)−0.0027 (19)
C270.026 (3)0.023 (2)0.018 (2)−0.001 (2)−0.007 (2)−0.0010 (19)
C280.020 (3)0.019 (2)0.016 (2)−0.0062 (19)0.0003 (19)−0.0056 (17)
C290.024 (3)0.019 (2)0.027 (2)−0.001 (2)−0.003 (2)−0.0050 (19)
C300.024 (3)0.027 (2)0.027 (3)−0.003 (2)0.004 (2)−0.011 (2)
C310.027 (3)0.025 (2)0.015 (2)−0.008 (2)0.004 (2)−0.0062 (18)
C320.025 (3)0.021 (2)0.017 (2)−0.005 (2)−0.0010 (19)−0.0025 (18)
C330.020 (3)0.017 (2)0.023 (2)−0.0011 (19)0.000 (2)−0.0051 (18)
C340.040 (3)0.024 (2)0.019 (2)−0.005 (2)−0.004 (2)−0.0048 (19)
C350.038 (3)0.025 (2)0.015 (2)−0.004 (2)−0.005 (2)0.0011 (19)
C360.039 (3)0.023 (2)0.028 (3)−0.003 (2)−0.010 (2)−0.001 (2)
C370.027 (3)0.026 (2)0.020 (2)−0.001 (2)−0.005 (2)−0.0006 (19)
C380.029 (3)0.023 (2)0.017 (2)−0.003 (2)−0.004 (2)−0.0005 (19)
C390.025 (3)0.018 (2)0.018 (2)0.004 (2)−0.003 (2)−0.0002 (18)
C400.028 (3)0.020 (2)0.022 (2)−0.003 (2)−0.003 (2)−0.0026 (19)
C410.021 (3)0.025 (2)0.025 (3)−0.002 (2)0.000 (2)−0.002 (2)
C420.023 (3)0.026 (2)0.020 (2)0.006 (2)0.001 (2)−0.0024 (19)
C430.028 (3)0.020 (2)0.020 (2)−0.004 (2)0.005 (2)−0.0034 (19)
C440.027 (3)0.019 (2)0.022 (2)−0.005 (2)−0.004 (2)−0.0028 (18)
Geometric parameters (Å, °)
Cl1—C91.747 (4)C15—H150.9500
Cl2—C201.734 (4)C16—H160.9500
Cl3—C311.751 (4)C17—C181.397 (6)
Cl4—C421.744 (5)C17—C221.400 (6)
N1—C51.345 (5)C18—C191.385 (6)
N1—C11.359 (5)C18—H180.9500
N2—C11.380 (5)C19—C201.391 (6)
N2—C61.406 (5)C19—H190.9500
N2—H2N0.8800C20—C211.386 (7)
N3—C161.338 (5)C21—C221.378 (6)
N3—C121.340 (6)C21—H210.9500
N4—C121.381 (5)C22—H220.9500
N4—C171.401 (5)C23—C241.376 (6)
N4—H4N0.8800C23—H230.9500
N5—C271.334 (6)C24—C251.385 (6)
N5—C231.335 (5)C24—H240.9500
N6—C271.370 (5)C25—C261.368 (6)
N6—C281.411 (5)C25—H250.9500
N6—H6N0.8800C26—C271.419 (6)
N7—C341.336 (5)C26—H260.9500
N7—C381.340 (6)C28—C291.385 (6)
N8—C391.386 (5)C28—C331.397 (6)
N8—C381.387 (5)C29—C301.387 (6)
N8—H8N0.8800C29—H290.9500
C1—C21.405 (6)C30—C311.385 (6)
C2—C31.382 (6)C30—H300.9500
C2—H20.9500C31—C321.369 (6)
C3—C41.384 (6)C32—C331.401 (6)
C3—H30.9500C32—H320.9500
C4—C51.378 (6)C33—H330.9500
C4—H40.9500C34—C351.376 (6)
C5—H50.9500C34—H340.9500
C6—C111.387 (5)C35—C361.389 (7)
C6—C71.393 (6)C35—H350.9500
C7—C81.394 (6)C36—C371.373 (6)
C7—H70.9500C36—H360.9500
C8—C91.377 (6)C37—C381.392 (6)
C8—H80.9500C37—H370.9500
C9—C101.391 (6)C39—C441.397 (6)
C10—C111.387 (6)C39—C401.403 (6)
C10—H100.9500C40—C411.381 (6)
C11—H110.9500C40—H400.9500
C12—C131.406 (6)C41—C421.393 (6)
C13—C141.377 (6)C41—H410.9500
C13—H130.9500C42—C431.376 (6)
C14—C151.390 (6)C43—C441.386 (6)
C14—H140.9500C43—H430.9500
C15—C161.371 (6)C44—H440.9500
C5—N1—C1117.0 (4)C21—C20—Cl2119.7 (3)
C1—N2—C6126.6 (4)C19—C20—Cl2119.1 (4)
C1—N2—H2N116.7C22—C21—C20118.7 (4)
C6—N2—H2N116.7C22—C21—H21120.6
C16—N3—C12117.9 (4)C20—C21—H21120.6
C12—N4—C17127.2 (4)C21—C22—C17121.8 (5)
C12—N4—H4N116.4C21—C22—H22119.1
C17—N4—H4N116.4C17—C22—H22119.1
C27—N5—C23117.4 (4)N5—C23—C24125.0 (4)
C27—N6—C28126.6 (4)N5—C23—H23117.5
C27—N6—H6N116.7C24—C23—H23117.5
C28—N6—H6N116.7C23—C24—C25117.0 (4)
C34—N7—C38117.1 (4)C23—C24—H24121.5
C39—N8—C38128.7 (4)C25—C24—H24121.5
C39—N8—H8N115.7C26—C25—C24120.4 (4)
C38—N8—H8N115.7C26—C25—H25119.8
N1—C1—N2113.7 (4)C24—C25—H25119.8
N1—C1—C2122.1 (4)C25—C26—C27118.2 (4)
N2—C1—C2124.2 (4)C25—C26—H26120.9
C3—C2—C1118.5 (4)C27—C26—H26120.9
C3—C2—H2120.7N5—C27—N6115.1 (4)
C1—C2—H2120.7N5—C27—C26122.1 (4)
C2—C3—C4120.2 (4)N6—C27—C26122.7 (4)
C2—C3—H3119.9C29—C28—C33119.6 (4)
C4—C3—H3119.9C29—C28—N6123.2 (4)
C5—C4—C3117.5 (4)C33—C28—N6117.2 (4)
C5—C4—H4121.2C28—C29—C30120.6 (4)
C3—C4—H4121.2C28—C29—H29119.7
N1—C5—C4124.7 (4)C30—C29—H29119.7
N1—C5—H5117.6C31—C30—C29119.0 (5)
C4—C5—H5117.6C31—C30—H30120.5
C11—C6—C7119.4 (4)C29—C30—H30120.5
C11—C6—N2118.3 (4)C32—C31—C30121.8 (4)
C7—C6—N2122.1 (4)C32—C31—Cl3119.1 (3)
C6—C7—C8119.5 (4)C30—C31—Cl3119.1 (4)
C6—C7—H7120.3C31—C32—C33119.2 (4)
C8—C7—H7120.3C31—C32—H32120.4
C9—C8—C7120.0 (4)C33—C32—H32120.4
C9—C8—H8120.0C28—C33—C32119.9 (4)
C7—C8—H8120.0C28—C33—H33120.1
C8—C9—C10121.5 (4)C32—C33—H33120.1
C8—C9—Cl1119.9 (3)N7—C34—C35124.7 (5)
C10—C9—Cl1118.6 (3)N7—C34—H34117.6
C11—C10—C9117.9 (4)C35—C34—H34117.6
C11—C10—H10121.0C34—C35—C36117.2 (4)
C9—C10—H10121.0C34—C35—H35121.4
C10—C11—C6121.7 (4)C36—C35—H35121.4
C10—C11—H11119.2C37—C36—C35119.5 (4)
C6—C11—H11119.2C37—C36—H36120.2
N3—C12—N4114.8 (4)C35—C36—H36120.2
N3—C12—C13122.1 (4)C36—C37—C38119.0 (5)
N4—C12—C13123.1 (4)C36—C37—H37120.5
C14—C13—C12118.5 (4)C38—C37—H37120.5
C14—C13—H13120.7N7—C38—N8114.3 (4)
C12—C13—H13120.7N7—C38—C37122.4 (4)
C13—C14—C15119.3 (4)N8—C38—C37123.2 (4)
C13—C14—H14120.4N8—C39—C44117.4 (4)
C15—C14—H14120.4N8—C39—C40124.2 (4)
C16—C15—C14118.3 (4)C44—C39—C40118.3 (4)
C16—C15—H15120.8C41—C40—C39120.2 (4)
C14—C15—H15120.8C41—C40—H40119.9
N3—C16—C15123.8 (4)C39—C40—H40119.9
N3—C16—H16118.1C40—C41—C42120.0 (4)
C15—C16—H16118.1C40—C41—H41120.0
C18—C17—C22118.2 (4)C42—C41—H41120.0
C18—C17—N4123.1 (4)C43—C42—C41120.8 (4)
C22—C17—N4118.6 (4)C43—C42—Cl4119.6 (3)
C19—C18—C17120.8 (4)C41—C42—Cl4119.6 (4)
C19—C18—H18119.6C42—C43—C44119.0 (4)
C17—C18—H18119.6C42—C43—H43120.5
C18—C19—C20119.2 (5)C44—C43—H43120.5
C18—C19—H19120.4C43—C44—C39121.6 (4)
C20—C19—H19120.4C43—C44—H44119.2
C21—C20—C19121.2 (4)C39—C44—H44119.2
C5—N1—C1—N2−178.5 (4)C27—N5—C23—C24−1.1 (7)
C5—N1—C1—C20.8 (6)N5—C23—C24—C251.6 (8)
C6—N2—C1—N1178.8 (4)C23—C24—C25—C26−1.5 (7)
C6—N2—C1—C2−0.5 (7)C24—C25—C26—C271.0 (7)
N1—C1—C2—C3−0.9 (7)C23—N5—C27—N6178.0 (4)
N2—C1—C2—C3178.3 (4)C23—N5—C27—C260.4 (7)
C1—C2—C3—C40.8 (7)C28—N6—C27—N5−174.5 (4)
C2—C3—C4—C5−0.6 (7)C28—N6—C27—C263.1 (7)
C1—N1—C5—C4−0.6 (7)C25—C26—C27—N5−0.4 (7)
C3—C4—C5—N10.5 (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—C748.5 (7)C27—N6—C28—C33128.5 (5)
C11—C6—C7—C82.9 (7)C33—C28—C29—C30−1.5 (6)
N2—C6—C7—C8178.4 (4)N6—C28—C29—C30−179.0 (4)
C6—C7—C8—C9−2.6 (7)C28—C29—C30—C311.7 (6)
C7—C8—C9—C100.8 (7)C29—C30—C31—C32−0.3 (7)
C7—C8—C9—Cl1−179.3 (4)C29—C30—C31—Cl3179.4 (3)
C8—C9—C10—C110.6 (7)C30—C31—C32—C33−1.2 (7)
Cl1—C9—C10—C11−179.2 (4)Cl3—C31—C32—C33179.1 (3)
C9—C10—C11—C6−0.3 (7)C29—C28—C33—C320.0 (6)
C7—C6—C11—C10−1.5 (7)N6—C28—C33—C32177.6 (4)
N2—C6—C11—C10−177.1 (4)C31—C32—C33—C281.4 (6)
C16—N3—C12—N4179.8 (4)C38—N7—C34—C350.9 (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—C372.9 (7)
C17—N4—C12—C1321.9 (8)C35—C36—C37—C380.2 (7)
N3—C12—C13—C141.6 (8)C34—N7—C38—N8−178.3 (4)
N4—C12—C13—C14179.9 (5)C34—N7—C38—C372.6 (7)
C12—C13—C14—C15−0.2 (7)C39—N8—C38—N7158.5 (5)
C13—C14—C15—C16−1.0 (8)C39—N8—C38—C37−22.4 (8)
C12—N3—C16—C150.6 (8)C36—C37—C38—N7−3.1 (7)
C14—C15—C16—N30.8 (8)C36—C37—C38—N8177.9 (5)
C12—N4—C17—C1830.0 (7)C38—N8—C39—C44159.5 (5)
C12—N4—C17—C22−153.9 (4)C38—N8—C39—C40−22.0 (8)
C22—C17—C18—C191.1 (6)N8—C39—C40—C41−179.1 (5)
N4—C17—C18—C19177.1 (4)C44—C39—C40—C41−0.6 (7)
C17—C18—C19—C20−1.4 (6)C39—C40—C41—C421.6 (7)
C18—C19—C20—C211.0 (6)C40—C41—C42—C43−0.8 (7)
C18—C19—C20—Cl2−178.3 (3)C40—C41—C42—Cl4178.5 (4)
C19—C20—C21—C22−0.3 (6)C41—C42—C43—C44−1.0 (7)
Cl2—C20—C21—C22179.0 (3)Cl4—C42—C43—C44179.7 (4)
C20—C21—C22—C170.0 (7)C42—C43—C44—C392.1 (7)
C18—C17—C22—C21−0.4 (6)N8—C39—C44—C43177.3 (4)
N4—C17—C22—C21−176.6 (4)C40—C39—C44—C43−1.2 (7)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
N2—H2n···N30.882.193.019 (5)156
N4—H4n···N10.882.173.010 (5)160
N6—H6n···N70.882.132.968 (5)158
N8—H8n···N50.882.253.096 (5)161
 
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2115).
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