Literature DB >> 21584031

4-(2,4-Dichloro-phen-yl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile.

P Ramesh, S S Sundaresan, P Thirumurugan, Paramasivan T Perumal, M N Ponnuswamy.   

Abstract

The title compound, C(25)H(14)Cl(2)N(4), crystallizes with two independent mol-ecules 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 mol-ecules. The dichloro-phenyl 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 inter-actions.

Entities:  

Year:  2009        PMID： 21584031      PMCID： PMC2977688          DOI： 10.1107/S1600536809012392

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C25H14Cl2N4 M = 441.30 Monoclinic, 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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). 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
C25H14Cl2N4F(000) = 1808
Mr = 441.30Dx = 1.452 Mg m−3
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 mm−1
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
Bruker Kappa APEXII area-detector diffractometer7874 independent reflections
Radiation source: fine-focus sealed tube5586 reflections with I > 2σ(I)
graphiteRint = 0.038
ω and φ 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 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 Å−3
0 restraintsΔρmin = −0.41 e Å−3
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.
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)
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)
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)
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
Table 1

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) ; (ii) ; (iii) . Cg5, Cg7 and Cg8 are the centroids of the C24–N29, C8–C13 and C8A–C13A rings, respectively.

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  G I Stevenson; A L Smith; S Lewis; S G Michie; J G Neduvelil; S Patel; R Marwood; S Patel; J L Castro
Journal:  Bioorg Med Chem Lett       Date:  2000-12-18       Impact factor: 2.823

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Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-07-23
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