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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o996–o997.
Published online 2009 April 8. doi:  10.1107/S1600536809012392
PMCID: PMC2977688

4-(2,4-Dichloro­phen­yl)-6-(1H-indol-3-yl)-2,2′-bipyridine-5-carbonitrile

Abstract

The title compound, C25H14Cl2N4, crystallizes with two independent mol­ecules in the asymmetric unit. The two pyridine rings are almost coplanar, making dihedral angles of 3.2 (1) and 8.6 (1)° in the two independent mol­ecules. The dichloro­phenyl and indole rings are twisted away from the bipyridine ring by 64.32 (5) and 18.46 (4)°, respectively in the first molecule and by 51.0 (1) and 27.99 (5)°, respectively in the second molecule. The crystal packing is stabilized by C—H(...)N, C—H(...)Cl, N—H(...)N and C—H(...)π inter­actions.

Related literature

For the use of pyridine derivatives containing cyano, amino, carboxyl and hydroxyl groups as drugs, see: Zhou et al. (2008 [triangle]); Stevenson et al. (2000 [triangle]); Harris & Uhle (1960 [triangle]); Ho et al. (1986 [triangle]); Rajeswaran et al. (1999 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o996-scheme1.jpg

Experimental

Crystal data

  • C25H14Cl2N4
  • M r = 441.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o996-efi1.jpg
  • a = 10.0307 (12) Å
  • b = 22.446 (3) Å
  • c = 17.932 (3) Å
  • β = 90.991 (4)°
  • V = 4036.7 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 293 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.902, T max = 0.934
  • 38628 measured reflections
  • 7874 independent reflections
  • 5586 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.141
  • S = 1.06
  • 7874 reflections
  • 567 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012392/bt2890sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012392/bt2890Isup2.hkl

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

Acknowledgments

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Pyridine derivatives containing multi-functional groups can be used as drugs such as streptonigrin, streptonigrone and lavendamycin which are reported as anticancer drugs, and itavastatin, cerivastatin are reported as the HMG-CoA enzyme inhibitors (Zhou et al., 2008). Indole derivatives are used as bioactive drugs (Stevenson et al., 2000) and they exhibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle 1960; Ho et al., 1986). Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999).

The ORTEP diagram of the title compound is shown in Fig. 1. In the title compound, there are two crystallographically independent molecules in the asymmetric unit. The two pyridine rings lie in the same plane as can be seen from the dihedral angle of 3.2 (1)° and 8.6 (1)°. The dichlorophenyl and indole rings are twisted away from the bipyridine ring by 64.32 (5)° and 18.46 (4)°, respectively. In the benzene ring of the indole ring system, the endocyclic angels at C12 and C12' are contracted to 117.7 (2)° and 117.9 (3)°, while those at C13 and C13' are expanded to 123.0 (2)° and 122.2 (3)°, respectively. This would appear to be a real effect caused by the fusion of the pyrrole with benzene ring resulting in an angular distortion. The sum of the bond angles around N14(359.3)° and N14'(360.3)° are in accordance with sp2 hybridization. The bond angles of C3—C16—N17 (178.0 (3))° and C3'-C16'-N17' (178.0 (3))° show the linearity of the cyano group, a feature observed in carbonitrile compounds.

The crystal packing is controlled by C—H···N, C—H···Cl, N—H···N and C—H···π types of intra and intermolecular interactions in addition to van der Waals forces. Atoms N14 and N14' at (x, y, z) donate one proton each to N17 (-x, y + 1/2, -z + 1/2) and N17'(-x, y - 1/2, -z + 1/2) which connects the molecules to form a dimer with a graph-set-motiff R22(16) (Bernstein et al., 1995). These dimers are linked into a zigzag chain running along b axis through intermolecular C5—H5···Cl2' hydrogen bond which is shown in Fig. 2.

Experimental

A mixture of 4-(2,4-dichlorophenyl)-6-(1H-indol-3-yl)-1,4-dihydro -2,2'-bipyridine-5-carbonitrile (1 mmol) and urea oxalate (20 mol%) was irradiated in a microwave oven in ethanol for 5 min. After the completion of the reaction (as monitored by TLC), it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuo. The crude product was chromatographed and isolated in 86% yield (90:10, petroleum ether: ethyl acetate). The compound was recrystallized in ethanol.

Refinement

H atoms bonded to nitrogen were freely refined; those bonded to carbon were positioned geometrically (C—H=0.93 Å) and allowed to ride on their parent atoms, with 1.2Ueq(C).

Figures

Fig. 1.
Perspective view of one of the two molecules in the asymmetric unit with displacement ellipsoids drawn at the 50% probability level. The H atoms are shown as small circles of arbitrary radii.
Fig. 2.
The crystal packing of the molecules viewed down c axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C25H14Cl2N4F(000) = 1808
Mr = 441.30Dx = 1.452 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4532 reflections
a = 10.0307 (12) Åθ = 1.5–26.0°
b = 22.446 (3) ŵ = 0.34 mm1
c = 17.932 (3) ÅT = 293 K
β = 90.991 (4)°Block, colourless
V = 4036.7 (10) Å30.30 × 0.25 × 0.20 mm
Z = 8

Data collection

Bruker Kappa APEXII area-detector diffractometer7874 independent reflections
Radiation source: fine-focus sealed tube5586 reflections with I > 2σ(I)
graphiteRint = 0.038
ω and [var phi] scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −12→12
Tmin = 0.902, Tmax = 0.934k = −27→27
38628 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0749P)2 + 1.173P] where P = (Fo2 + 2Fc2)/3
7874 reflections(Δ/σ)max = 0.002
567 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = −0.41 e Å3

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.
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 > σ(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)

xyzUiso*/Ueq
Cl10.45103 (8)0.83228 (3)−0.01221 (4)0.0625 (2)
Cl1'1.02167 (6)0.57914 (3)0.01576 (4)0.04880 (18)
Cl20.36009 (7)0.60707 (3)0.06685 (5)0.0571 (2)
Cl2'0.83340 (8)0.80040 (3)0.03850 (6)0.0715 (3)
N10.20249 (18)0.98708 (8)0.13679 (11)0.0348 (4)
N1'0.74187 (17)0.42415 (8)0.15496 (11)0.0344 (4)
C20.3239 (2)0.96455 (10)0.15411 (12)0.0341 (5)
C2'0.8626 (2)0.44706 (10)0.17186 (12)0.0324 (5)
C30.3509 (2)0.90381 (10)0.14152 (13)0.0356 (5)
C3'0.8898 (2)0.50742 (10)0.15868 (13)0.0344 (5)
C40.2523 (2)0.86696 (10)0.11020 (13)0.0346 (5)
C4'0.7929 (2)0.54340 (10)0.12346 (13)0.0331 (5)
C50.1296 (2)0.89156 (10)0.09365 (14)0.0379 (5)
H50.06170.86820.07330.046*
C5'0.6708 (2)0.51797 (10)0.10687 (13)0.0360 (5)
H5'0.60400.54040.08370.043*
C60.1082 (2)0.95146 (10)0.10757 (13)0.0338 (5)
C6'0.6482 (2)0.45913 (10)0.12483 (13)0.0336 (5)
C70.4203 (2)1.00692 (11)0.18467 (13)0.0363 (5)
C7'0.9576 (2)0.40339 (10)0.20169 (13)0.0341 (5)
C80.4100 (2)1.07118 (10)0.18173 (13)0.0361 (5)
C8'0.9477 (2)0.33985 (11)0.19115 (14)0.0379 (5)
C90.3196 (2)1.11211 (11)0.15114 (14)0.0422 (6)
H90.24351.09900.12580.051*
C9'0.8629 (3)0.30236 (12)0.15088 (17)0.0496 (7)
H9'0.79160.31790.12330.060*
C100.3444 (3)1.17177 (12)0.15879 (16)0.0486 (6)
H100.28421.19900.13830.058*
C10'0.8856 (3)0.24218 (13)0.1523 (2)0.0661 (9)
H10'0.82890.21710.12530.079*
C110.4577 (3)1.19271 (12)0.19653 (16)0.0526 (7)
H110.47111.23350.20160.063*
C11'0.9914 (3)0.21783 (13)0.1930 (2)0.0681 (9)
H11'1.00340.17670.19370.082*
C120.5494 (3)1.15379 (12)0.22616 (15)0.0489 (7)
H120.62631.16740.25040.059*
C12'1.0781 (3)0.25361 (13)0.23219 (18)0.0573 (8)
H12'1.14990.23750.25880.069*
C130.5240 (2)1.09366 (11)0.21879 (14)0.0399 (6)
C13'1.0555 (2)0.31442 (12)0.23096 (14)0.0422 (6)
N140.5971 (2)1.04600 (10)0.24325 (13)0.0462 (6)
H140.662 (3)1.0477 (14)0.2631 (17)0.057 (10)*
N14'1.1256 (2)0.35976 (10)0.26389 (12)0.0447 (5)
H14'1.197 (3)0.3551 (13)0.2910 (16)0.056 (9)*
C150.5373 (2)0.99500 (12)0.22312 (14)0.0432 (6)
H150.56990.95710.23360.052*
C15'1.0688 (2)0.41225 (12)0.24621 (13)0.0398 (6)
H15'1.10020.44930.26190.048*
C160.4777 (3)0.87749 (11)0.15980 (15)0.0437 (6)
C16'1.0143 (2)0.53357 (11)0.18177 (14)0.0405 (6)
N170.5778 (2)0.85535 (11)0.17464 (15)0.0609 (7)
N17'1.1115 (2)0.55515 (11)0.20191 (14)0.0582 (6)
C180.2769 (2)0.80267 (10)0.09598 (13)0.0352 (5)
C18'0.8131 (2)0.60717 (10)0.10453 (13)0.0345 (5)
C190.3670 (2)0.78254 (11)0.04386 (14)0.0385 (5)
C19'0.9112 (2)0.62789 (10)0.05739 (14)0.0374 (5)
C200.3917 (2)0.72262 (11)0.03353 (15)0.0443 (6)
H200.45350.7100−0.00120.053*
C20'0.9179 (2)0.68721 (11)0.03654 (15)0.0431 (6)
H20'0.98430.70050.00500.052*
C210.3230 (2)0.68196 (11)0.07557 (14)0.0408 (6)
C21'0.8242 (3)0.72612 (11)0.06352 (16)0.0452 (6)
C220.2279 (2)0.70021 (11)0.12538 (15)0.0435 (6)
H220.17880.67230.15170.052*
C22'0.7246 (3)0.70747 (11)0.11006 (16)0.0491 (7)
H22'0.66170.73430.12740.059*
C230.2068 (2)0.76007 (11)0.13554 (14)0.0407 (6)
H230.14390.77240.16980.049*
C23'0.7198 (3)0.64864 (11)0.13038 (15)0.0447 (6)
H23'0.65310.63590.16210.054*
C24−0.0246 (2)0.97866 (10)0.09155 (13)0.0354 (5)
C24'0.5145 (2)0.43164 (10)0.11345 (13)0.0326 (5)
C25−0.0512 (3)1.03740 (11)0.10704 (16)0.0472 (6)
H250.01521.06200.12670.057*
C25'0.4913 (2)0.37279 (11)0.13089 (15)0.0437 (6)
H25'0.56060.34830.14720.052*
C26−0.1781 (3)1.05944 (13)0.09294 (17)0.0558 (7)
H26−0.19821.09900.10310.067*
C26'0.3625 (3)0.35088 (12)0.12371 (16)0.0500 (7)
H26'0.34390.31140.13520.060*
C27−0.2730 (3)1.02249 (13)0.06407 (17)0.0531 (7)
H27−0.35921.03610.05440.064*
C27'0.2636 (2)0.38809 (12)0.09957 (14)0.0432 (6)
H27'0.17610.37470.09500.052*
C28−0.2384 (3)0.96470 (13)0.04952 (17)0.0515 (7)
H28−0.30340.93960.02940.062*
C28'0.2955 (2)0.44533 (12)0.08230 (15)0.0438 (6)
H28'0.22750.47020.06510.053*
N29−0.1168 (2)0.94216 (9)0.06248 (13)0.0453 (5)
N29'0.41791 (19)0.46807 (9)0.08843 (12)0.0402 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0732 (5)0.0578 (4)0.0573 (4)−0.0020 (4)0.0262 (4)0.0068 (3)
Cl1'0.0403 (3)0.0521 (4)0.0542 (4)0.0078 (3)0.0067 (3)0.0029 (3)
Cl20.0517 (4)0.0350 (3)0.0842 (5)0.0091 (3)−0.0060 (4)−0.0091 (3)
Cl2'0.0753 (5)0.0338 (4)0.1049 (7)−0.0035 (3)−0.0140 (5)0.0104 (4)
N10.0330 (10)0.0340 (10)0.0375 (11)0.0009 (8)0.0003 (8)−0.0003 (9)
N1'0.0271 (9)0.0352 (10)0.0408 (11)0.0017 (8)−0.0008 (8)0.0008 (9)
C20.0345 (12)0.0363 (12)0.0316 (12)0.0002 (10)0.0013 (10)0.0017 (10)
C2'0.0293 (11)0.0369 (12)0.0310 (12)0.0018 (9)0.0015 (9)−0.0005 (10)
C30.0305 (11)0.0380 (13)0.0383 (13)0.0029 (10)−0.0001 (10)−0.0001 (10)
C3'0.0290 (11)0.0392 (13)0.0350 (12)−0.0016 (10)−0.0013 (9)−0.0003 (10)
C40.0341 (12)0.0345 (12)0.0355 (13)0.0012 (10)0.0047 (10)−0.0001 (10)
C4'0.0312 (11)0.0330 (12)0.0351 (13)−0.0007 (9)−0.0012 (9)−0.0011 (10)
C50.0332 (12)0.0358 (13)0.0448 (14)−0.0016 (10)0.0013 (10)−0.0013 (11)
C5'0.0305 (12)0.0358 (13)0.0417 (13)0.0026 (10)−0.0035 (10)0.0043 (10)
C60.0314 (12)0.0339 (12)0.0360 (13)0.0004 (10)0.0041 (10)0.0019 (10)
C6'0.0292 (11)0.0362 (12)0.0352 (13)0.0018 (9)−0.0017 (9)−0.0004 (10)
C70.0361 (12)0.0386 (13)0.0340 (13)0.0002 (10)0.0001 (10)−0.0013 (10)
C7'0.0284 (11)0.0390 (13)0.0349 (12)0.0035 (9)0.0008 (9)0.0051 (10)
C80.0334 (12)0.0406 (13)0.0343 (13)−0.0016 (10)0.0017 (10)−0.0035 (10)
C8'0.0298 (12)0.0420 (13)0.0421 (14)0.0070 (10)0.0031 (10)0.0060 (11)
C90.0354 (13)0.0425 (14)0.0486 (15)0.0003 (11)−0.0015 (11)0.0004 (12)
C9'0.0389 (14)0.0434 (15)0.0662 (19)0.0045 (11)−0.0047 (13)−0.0024 (13)
C100.0467 (15)0.0417 (14)0.0573 (17)0.0029 (12)0.0011 (13)0.0037 (12)
C10'0.0569 (18)0.0440 (16)0.097 (3)0.0054 (14)−0.0042 (17)−0.0104 (16)
C110.0599 (17)0.0383 (14)0.0596 (18)−0.0090 (13)0.0019 (14)−0.0017 (13)
C11'0.069 (2)0.0391 (16)0.097 (3)0.0152 (15)0.0030 (19)0.0016 (16)
C120.0498 (15)0.0476 (15)0.0492 (16)−0.0113 (12)−0.0048 (12)−0.0068 (13)
C12'0.0514 (17)0.0542 (17)0.0664 (19)0.0215 (14)0.0034 (15)0.0135 (15)
C130.0379 (13)0.0435 (14)0.0381 (13)−0.0022 (11)−0.0012 (11)−0.0036 (11)
C13'0.0351 (13)0.0477 (14)0.0439 (14)0.0076 (11)0.0033 (11)0.0103 (12)
N140.0397 (13)0.0494 (14)0.0490 (14)−0.0009 (11)−0.0137 (11)−0.0028 (10)
N14'0.0338 (11)0.0575 (14)0.0426 (12)0.0090 (10)−0.0059 (10)0.0091 (11)
C150.0415 (14)0.0438 (14)0.0442 (15)0.0032 (11)−0.0062 (11)−0.0001 (12)
C15'0.0372 (13)0.0465 (14)0.0357 (13)0.0044 (11)−0.0013 (10)0.0029 (11)
C160.0412 (14)0.0415 (14)0.0483 (15)0.0028 (11)−0.0054 (12)−0.0072 (12)
C16'0.0385 (13)0.0399 (13)0.0429 (14)−0.0022 (11)−0.0076 (11)0.0062 (11)
N170.0496 (14)0.0586 (15)0.0739 (18)0.0139 (12)−0.0148 (12)−0.0155 (13)
N17'0.0469 (14)0.0605 (15)0.0666 (16)−0.0129 (12)−0.0207 (12)0.0127 (13)
C180.0320 (12)0.0350 (12)0.0385 (13)0.0039 (10)−0.0013 (10)−0.0007 (10)
C18'0.0316 (12)0.0335 (12)0.0382 (13)−0.0033 (10)−0.0077 (10)−0.0022 (10)
C190.0385 (13)0.0389 (13)0.0381 (13)0.0023 (10)0.0030 (10)−0.0001 (11)
C19'0.0332 (12)0.0374 (13)0.0413 (14)−0.0004 (10)−0.0071 (10)−0.0016 (11)
C200.0407 (14)0.0474 (15)0.0448 (15)0.0079 (12)0.0024 (11)−0.0085 (12)
C20'0.0394 (13)0.0422 (14)0.0474 (15)−0.0088 (11)−0.0064 (11)0.0039 (12)
C210.0384 (13)0.0340 (13)0.0498 (15)0.0078 (10)−0.0104 (11)−0.0044 (11)
C21'0.0493 (15)0.0301 (12)0.0557 (17)−0.0032 (11)−0.0143 (13)−0.0011 (11)
C220.0396 (13)0.0370 (13)0.0540 (16)0.0010 (11)0.0004 (12)0.0047 (12)
C22'0.0453 (15)0.0378 (14)0.0639 (18)0.0051 (12)−0.0039 (13)−0.0102 (13)
C230.0341 (12)0.0412 (13)0.0471 (15)0.0029 (10)0.0074 (11)−0.0008 (11)
C23'0.0420 (14)0.0379 (14)0.0540 (16)−0.0009 (11)−0.0022 (12)−0.0042 (12)
C240.0346 (12)0.0356 (12)0.0361 (13)0.0006 (10)0.0027 (10)0.0042 (10)
C24'0.0297 (11)0.0322 (12)0.0359 (12)0.0004 (9)0.0004 (9)−0.0017 (10)
C250.0441 (14)0.0373 (14)0.0602 (17)0.0026 (11)0.0002 (12)−0.0029 (12)
C25'0.0341 (12)0.0362 (13)0.0609 (17)0.0012 (10)−0.0027 (11)0.0045 (12)
C260.0502 (16)0.0444 (15)0.073 (2)0.0140 (13)0.0011 (14)−0.0004 (14)
C26'0.0437 (15)0.0406 (14)0.0658 (18)−0.0089 (12)0.0011 (13)0.0059 (13)
C270.0385 (14)0.0565 (17)0.0643 (19)0.0120 (13)0.0006 (13)0.0111 (14)
C27'0.0311 (12)0.0534 (16)0.0449 (15)−0.0092 (11)−0.0020 (11)−0.0012 (12)
C280.0352 (14)0.0536 (16)0.0655 (19)−0.0027 (12)−0.0071 (12)0.0070 (14)
C28'0.0304 (12)0.0502 (15)0.0506 (15)0.0023 (11)−0.0074 (11)0.0024 (12)
N290.0360 (11)0.0408 (12)0.0590 (14)0.0006 (9)−0.0040 (10)0.0030 (10)
N29'0.0314 (10)0.0377 (11)0.0512 (13)0.0009 (9)−0.0079 (9)0.0027 (9)

Geometric parameters (Å, °)

Cl1—C191.731 (3)C12'—H12'0.9300
Cl1'—C19'1.735 (2)C13—N141.365 (3)
Cl2—C211.729 (2)C13'—N14'1.365 (3)
Cl2'—C21'1.729 (3)N14—C151.339 (3)
N1—C61.338 (3)N14—H140.73 (3)
N1—C21.350 (3)N14'—C15'1.344 (3)
N1'—C6'1.332 (3)N14'—H14'0.86 (3)
N1'—C2'1.346 (3)C15—H150.9300
C2—C31.409 (3)C15'—H15'0.9300
C2—C71.457 (3)C16—N171.147 (3)
C2'—C3'1.403 (3)C16'—N17'1.142 (3)
C2'—C7'1.462 (3)C18—C191.387 (3)
C3—C41.400 (3)C18—C231.389 (3)
C3—C161.435 (3)C18'—C19'1.389 (3)
C3'—C4'1.406 (3)C18'—C23'1.404 (3)
C3'—C16'1.434 (3)C19—C201.380 (3)
C4—C51.377 (3)C19'—C20'1.385 (3)
C4—C181.487 (3)C20—C211.376 (4)
C4'—C5'1.379 (3)C20—H200.9300
C4'—C18'1.486 (3)C20'—C21'1.377 (4)
C5—C61.385 (3)C20'—H20'0.9300
C5—H50.9300C21—C221.380 (4)
C5'—C6'1.379 (3)C21'—C22'1.378 (4)
C5'—H5'0.9300C22—C231.373 (3)
C6—C241.489 (3)C22—H220.9300
C6'—C24'1.487 (3)C22'—C23'1.371 (4)
C7—C151.376 (3)C22'—H22'0.9300
C7—C81.447 (3)C23—H230.9300
C7'—C15'1.375 (3)C23'—H23'0.9300
C7'—C8'1.442 (3)C24—N291.335 (3)
C8—C91.396 (3)C24—C251.374 (3)
C8—C131.406 (3)C24'—N29'1.339 (3)
C8'—C9'1.390 (4)C24'—C25'1.378 (3)
C8'—C13'1.406 (3)C25—C261.386 (4)
C9—C101.368 (4)C25—H250.9300
C9—H90.9300C25'—C26'1.386 (3)
C9'—C10'1.370 (4)C25'—H25'0.9300
C9'—H9'0.9300C26—C271.358 (4)
C10—C111.394 (4)C26—H260.9300
C10—H100.9300C26'—C27'1.361 (4)
C10'—C11'1.390 (4)C26'—H26'0.9300
C10'—H10'0.9300C27—C281.369 (4)
C11—C121.370 (4)C27—H270.9300
C11—H110.9300C27'—C28'1.361 (4)
C11'—C12'1.369 (4)C27'—H27'0.9300
C11'—H11'0.9300C28—N291.337 (3)
C12—C131.380 (4)C28—H280.9300
C12—H120.9300C28'—N29'1.332 (3)
C12'—C13'1.384 (4)C28'—H28'0.9300
C6—N1—C2119.67 (19)C15'—N14'—H14'126 (2)
C6'—N1'—C2'119.48 (19)C13'—N14'—H14'124.5 (19)
N1—C2—C3120.1 (2)N14—C15—C7110.1 (2)
N1—C2—C7115.6 (2)N14—C15—H15125.0
C3—C2—C7124.3 (2)C7—C15—H15125.0
N1'—C2'—C3'120.5 (2)N14'—C15'—C7'110.3 (2)
N1'—C2'—C7'113.9 (2)N14'—C15'—H15'124.9
C3'—C2'—C7'125.6 (2)C7'—C15'—H15'124.9
C4—C3—C2120.0 (2)N17—C16—C3178.6 (3)
C4—C3—C16117.8 (2)N17'—C16'—C3'178.0 (3)
C2—C3—C16122.3 (2)C19—C18—C23117.5 (2)
C2'—C3'—C4'119.7 (2)C19—C18—C4122.9 (2)
C2'—C3'—C16'121.2 (2)C23—C18—C4119.6 (2)
C4'—C3'—C16'119.1 (2)C19'—C18'—C23'117.5 (2)
C5—C4—C3118.2 (2)C19'—C18'—C4'124.2 (2)
C5—C4—C18120.2 (2)C23'—C18'—C4'118.0 (2)
C3—C4—C18121.6 (2)C20—C19—C18121.9 (2)
C5'—C4'—C3'117.7 (2)C20—C19—Cl1117.41 (19)
C5'—C4'—C18'118.3 (2)C18—C19—Cl1120.71 (19)
C3'—C4'—C18'124.0 (2)C20'—C19'—C18'121.6 (2)
C4—C5—C6119.4 (2)C20'—C19'—Cl1'117.12 (19)
C4—C5—H5120.3C18'—C19'—Cl1'121.02 (18)
C6—C5—H5120.3C21—C20—C19118.7 (2)
C4'—C5'—C6'119.7 (2)C21—C20—H20120.7
C4'—C5'—H5'120.2C19—C20—H20120.7
C6'—C5'—H5'120.2C21'—C20'—C19'118.6 (2)
N1—C6—C5122.7 (2)C21'—C20'—H20'120.7
N1—C6—C24117.0 (2)C19'—C20'—H20'120.7
C5—C6—C24120.3 (2)C20—C21—C22121.0 (2)
N1'—C6'—C5'122.8 (2)C20—C21—Cl2119.0 (2)
N1'—C6'—C24'116.1 (2)C22—C21—Cl2119.9 (2)
C5'—C6'—C24'121.1 (2)C20'—C21'—C22'121.8 (2)
C15—C7—C8105.8 (2)C20'—C21'—Cl2'118.7 (2)
C15—C7—C2128.0 (2)C22'—C21'—Cl2'119.5 (2)
C8—C7—C2126.2 (2)C23—C22—C21119.1 (2)
C15'—C7'—C8'105.8 (2)C23—C22—H22120.5
C15'—C7'—C2'129.2 (2)C21—C22—H22120.5
C8'—C7'—C2'124.9 (2)C23'—C22'—C21'118.9 (2)
C9—C8—C13117.8 (2)C23'—C22'—H22'120.6
C9—C8—C7135.7 (2)C21'—C22'—H22'120.6
C13—C8—C7106.4 (2)C22—C23—C18121.7 (2)
C9'—C8'—C13'118.4 (2)C22—C23—H23119.2
C9'—C8'—C7'135.0 (2)C18—C23—H23119.2
C13'—C8'—C7'106.5 (2)C22'—C23'—C18'121.6 (3)
C10—C9—C8119.3 (2)C22'—C23'—H23'119.2
C10—C9—H9120.3C18'—C23'—H23'119.2
C8—C9—H9120.3N29—C24—C25122.1 (2)
C10'—C9'—C8'119.2 (3)N29—C24—C6115.8 (2)
C10'—C9'—H9'120.4C25—C24—C6122.0 (2)
C8'—C9'—H9'120.4N29'—C24'—C25'122.5 (2)
C9—C10—C11121.6 (3)N29'—C24'—C6'115.98 (19)
C9—C10—H10119.2C25'—C24'—C6'121.5 (2)
C11—C10—H10119.2C24—C25—C26119.1 (2)
C9'—C10'—C11'121.5 (3)C24—C25—H25120.4
C9'—C10'—H10'119.3C26—C25—H25120.4
C11'—C10'—H10'119.3C24'—C25'—C26'118.7 (2)
C12—C11—C10120.7 (2)C24'—C25'—H25'120.7
C12—C11—H11119.7C26'—C25'—H25'120.7
C10—C11—H11119.7C27—C26—C25119.2 (3)
C12'—C11'—C10'120.8 (3)C27—C26—H26120.4
C12'—C11'—H11'119.6C25—C26—H26120.4
C10'—C11'—H11'119.6C27'—C26'—C25'119.0 (2)
C11—C12—C13117.7 (2)C27'—C26'—H26'120.5
C11—C12—H12121.1C25'—C26'—H26'120.5
C13—C12—H12121.1C26—C27—C28118.2 (2)
C11'—C12'—C13'117.9 (3)C26—C27—H27120.9
C11'—C12'—H12'121.0C28—C27—H27120.9
C13'—C12'—H12'121.0C28'—C27'—C26'118.6 (2)
N14—C13—C12129.7 (2)C28'—C27'—H27'120.7
N14—C13—C8107.4 (2)C26'—C27'—H27'120.7
C12—C13—C8123.0 (2)N29—C28—C27124.0 (3)
N14'—C13'—C12'130.2 (2)N29—C28—H28118.0
N14'—C13'—C8'107.6 (2)C27—C28—H28118.0
C12'—C13'—C8'122.2 (3)N29'—C28'—C27'124.2 (2)
C15—N14—C13110.3 (2)N29'—C28'—H28'117.9
C15—N14—H14124 (2)C27'—C28'—H28'117.9
C13—N14—H14125 (2)C24—N29—C28117.4 (2)
C15'—N14'—C13'109.8 (2)C28'—N29'—C24'117.0 (2)
C6—N1—C2—C3−0.1 (3)C8—C13—N14—C150.8 (3)
C6—N1—C2—C7179.2 (2)C12'—C13'—N14'—C15'178.6 (3)
C6'—N1'—C2'—C3'0.6 (3)C8'—C13'—N14'—C15'−0.8 (3)
C6'—N1'—C2'—C7'−177.6 (2)C13—N14—C15—C7−0.5 (3)
N1—C2—C3—C40.8 (3)C8—C7—C15—N140.0 (3)
C7—C2—C3—C4−178.5 (2)C2—C7—C15—N14−178.8 (2)
N1—C2—C3—C16−179.2 (2)C13'—N14'—C15'—C7'0.9 (3)
C7—C2—C3—C161.6 (4)C8'—C7'—C15'—N14'−0.6 (3)
N1'—C2'—C3'—C4'−3.8 (3)C2'—C7'—C15'—N14'177.3 (2)
C7'—C2'—C3'—C4'174.2 (2)C4—C3—C16—N17−28 (12)
N1'—C2'—C3'—C16'175.0 (2)C2—C3—C16—N17152 (12)
C7'—C2'—C3'—C16'−7.0 (4)C2'—C3'—C16'—N17'−103 (8)
C2—C3—C4—C5−1.1 (3)C4'—C3'—C16'—N17'76 (8)
C16—C3—C4—C5178.9 (2)C5—C4—C18—C19114.7 (3)
C2—C3—C4—C18180.0 (2)C3—C4—C18—C19−66.4 (3)
C16—C3—C4—C18−0.1 (3)C5—C4—C18—C23−64.7 (3)
C2'—C3'—C4'—C5'3.5 (3)C3—C4—C18—C23114.2 (3)
C16'—C3'—C4'—C5'−175.4 (2)C5'—C4'—C18'—C19'−121.2 (3)
C2'—C3'—C4'—C18'−177.8 (2)C3'—C4'—C18'—C19'60.1 (3)
C16'—C3'—C4'—C18'3.4 (4)C5'—C4'—C18'—C23'52.8 (3)
C3—C4—C5—C60.7 (3)C3'—C4'—C18'—C23'−126.0 (3)
C18—C4—C5—C6179.7 (2)C23—C18—C19—C20−3.0 (4)
C3'—C4'—C5'—C6'−0.2 (3)C4—C18—C19—C20177.6 (2)
C18'—C4'—C5'—C6'−179.0 (2)C23—C18—C19—Cl1175.85 (18)
C2—N1—C6—C5−0.3 (3)C4—C18—C19—Cl1−3.6 (3)
C2—N1—C6—C24178.4 (2)C23'—C18'—C19'—C20'0.2 (3)
C4—C5—C6—N10.0 (4)C4'—C18'—C19'—C20'174.2 (2)
C4—C5—C6—C24−178.7 (2)C23'—C18'—C19'—Cl1'−174.10 (18)
C2'—N1'—C6'—C5'2.9 (3)C4'—C18'—C19'—Cl1'−0.1 (3)
C2'—N1'—C6'—C24'−175.3 (2)C18—C19—C20—C211.0 (4)
C4'—C5'—C6'—N1'−3.1 (4)Cl1—C19—C20—C21−177.85 (19)
C4'—C5'—C6'—C24'175.0 (2)C18'—C19'—C20'—C21'−0.1 (4)
N1—C2—C7—C15163.0 (2)Cl1'—C19'—C20'—C21'174.42 (19)
C3—C2—C7—C15−17.8 (4)C19—C20—C21—C222.2 (4)
N1—C2—C7—C8−15.6 (3)C19—C20—C21—Cl2−176.34 (19)
C3—C2—C7—C8163.7 (2)C19'—C20'—C21'—C22'−0.3 (4)
N1'—C2'—C7'—C15'−156.2 (2)C19'—C20'—C21'—Cl2'179.25 (19)
C3'—C2'—C7'—C15'25.6 (4)C20—C21—C22—C23−3.3 (4)
N1'—C2'—C7'—C8'21.3 (3)Cl2—C21—C22—C23175.3 (2)
C3'—C2'—C7'—C8'−156.9 (2)C20'—C21'—C22'—C23'0.6 (4)
C15—C7—C8—C9179.0 (3)Cl2'—C21'—C22'—C23'−179.0 (2)
C2—C7—C8—C9−2.2 (4)C21—C22—C23—C181.2 (4)
C15—C7—C8—C130.5 (3)C19—C18—C23—C221.8 (4)
C2—C7—C8—C13179.3 (2)C4—C18—C23—C22−178.7 (2)
C15'—C7'—C8'—C9'−177.3 (3)C21'—C22'—C23'—C18'−0.5 (4)
C2'—C7'—C8'—C9'4.7 (4)C19'—C18'—C23'—C22'0.1 (4)
C15'—C7'—C8'—C13'0.1 (3)C4'—C18'—C23'—C22'−174.3 (2)
C2'—C7'—C8'—C13'−177.9 (2)N1—C6—C24—N29−180.0 (2)
C13—C8—C9—C10−0.6 (4)C5—C6—C24—N29−1.2 (3)
C7—C8—C9—C10−179.0 (3)N1—C6—C24—C25−1.1 (3)
C13'—C8'—C9'—C10'1.1 (4)C5—C6—C24—C25177.7 (2)
C7'—C8'—C9'—C10'178.3 (3)N1'—C6'—C24'—N29'175.1 (2)
C8—C9—C10—C11−0.1 (4)C5'—C6'—C24'—N29'−3.0 (3)
C8'—C9'—C10'—C11'0.0 (5)N1'—C6'—C24'—C25'−2.1 (3)
C9—C10—C11—C121.2 (4)C5'—C6'—C24'—C25'179.7 (2)
C9'—C10'—C11'—C12'−1.2 (5)N29—C24—C25—C260.8 (4)
C10—C11—C12—C13−1.5 (4)C6—C24—C25—C26−178.0 (2)
C10'—C11'—C12'—C13'1.2 (5)N29'—C24'—C25'—C26'−1.4 (4)
C11—C12—C13—N14−179.4 (3)C6'—C24'—C25'—C26'175.7 (2)
C11—C12—C13—C80.8 (4)C24—C25—C26—C27−0.1 (4)
C9—C8—C13—N14−179.6 (2)C24'—C25'—C26'—C27'0.1 (4)
C7—C8—C13—N14−0.8 (3)C25—C26—C27—C28−0.5 (4)
C9—C8—C13—C120.2 (4)C25'—C26'—C27'—C28'1.0 (4)
C7—C8—C13—C12179.0 (2)C26—C27—C28—N290.5 (5)
C11'—C12'—C13'—N14'−179.3 (3)C26'—C27'—C28'—N29'−1.0 (4)
C11'—C12'—C13'—C8'0.0 (4)C25—C24—N29—C28−0.8 (4)
C9'—C8'—C13'—N14'178.4 (2)C6—C24—N29—C28178.0 (2)
C7'—C8'—C13'—N14'0.4 (3)C27—C28—N29—C240.2 (4)
C9'—C8'—C13'—C12'−1.1 (4)C27'—C28'—N29'—C24'−0.2 (4)
C7'—C8'—C13'—C12'−179.1 (2)C25'—C24'—N29'—C28'1.4 (4)
C12—C13—N14—C15−179.0 (3)C6'—C24'—N29'—C28'−175.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9···N10.932.553.052 (3)114
C9'—H9'···N1'0.932.502.993 (3)113
C15—H15···N170.932.523.280 (4)139
C15'—H15'···N17'0.932.613.334 (3)135
C5—H5···Cl2'i0.932.813.727 (3)169
N14—H14···N17'ii0.73 (3)2.36 (3)3.075 (3)166 (3)
N14'—H14'···N17iii0.86 (3)2.33 (3)3.157 (3)160 (3)
C15'—H15'···Cg50.933.133.798 (3)131
C23—H23···Cg80.932.763.620 (3)155
C23'—H23'···Cg70.932.833.633 (3)145

Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2890).

References

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