Literature DB >> 21579118

5-(4-Chloro-phen-yl)-3-(2-fur-yl)-1,2,4-triazolo[3,4-a]isoquinoline.

F Nawaz Khan, P Manivel, K Prabakarana, Venkatesha R Hathwar, Mehmet Akkurt.   

Abstract

In the title mol-ecule, C(20)H(12)ClN(3)O, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.018 (3) Å and a maximum deviation of 0.034 (3) Å from the mean plane for the triazole ring C atom which is bonded to the benzene ring. The furan and benzene rings are twisted by 59.71 (14) and 66.95 (10)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The mol-ecular conformation is stabilized by an intra-molecular π-π inter-action [centroid-to-centroid distance = 3.5262 (18) Å]. The crystal packing is stabilized by weak C-H⋯π inter-actions and weak π-π inter-actions [centroid-to-centroid distance = 3.9431 (17) Å].

Entities:  

Year:  2010        PMID： 21579118      PMCID： PMC2979100          DOI： 10.1107/S1600536810012924

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


Related literature

For a related crystal structure, see: Khan et al. (2010 ▶).

Experimental

Crystal data

C20H12ClN3O M = 345.78 Orthorhombic, a = 9.0281 (9) Å b = 12.6034 (11) Å c = 14.6444 (15) Å V = 1666.3 (3) Å3 Z = 4 Mo Kα radiation μ = 0.24 mm−1 T = 290 K 0.32 × 0.24 × 0.15 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.933, T max = 0.964 9280 measured reflections 3029 independent reflections 1831 reflections with I > 2σ(I) R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.082 S = 0.85 3029 reflections 227 parameters H-atom parameters constrained Δρmax = 0.13 e Å−3 Δρmin = −0.14 e Å−3 Absolute structure: Flack (1983 ▶), with 1245 Freidel pairs Flack parameter: 0.00 (8) Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012924/pv2272sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012924/pv2272Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H12ClN3OF(000) = 712
Mr = 345.78Dx = 1.378 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1165 reflections
a = 9.0281 (9) Åθ = 1.7–20.6°
b = 12.6034 (11) ŵ = 0.24 mm−1
c = 14.6444 (15) ÅT = 290 K
V = 1666.3 (3) Å3Block, colourless
Z = 40.32 × 0.24 × 0.15 mm
Oxford Xcalibur Eos (Nova) CCD detector diffractometer3029 independent reflections
Radiation source: Enhance (Mo) X-ray Source1831 reflections with I > 2σ(I)
graphiteRint = 0.071
ω scansθmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)h = −8→10
Tmin = 0.933, Tmax = 0.964k = −14→15
9280 measured reflectionsl = −17→17
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041w = 1/[σ2(Fo2) + (0.0329P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082(Δ/σ)max = 0.001
S = 0.85Δρmax = 0.13 e Å−3
3029 reflectionsΔρmin = −0.14 e Å−3
227 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc* = kFc[1+0.001Fc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0109 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 1245 Freidel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.00 (8)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl10.33125 (9)1.00293 (7)0.16049 (6)0.0937 (3)
O10.5357 (2)0.77175 (16)0.41053 (13)0.0713 (8)
N10.3343 (2)0.56533 (14)0.42785 (13)0.0434 (7)
N20.4295 (2)0.58135 (18)0.56552 (15)0.0607 (9)
N30.3791 (3)0.47806 (17)0.55611 (15)0.0588 (8)
C10.3237 (3)0.46973 (19)0.47266 (18)0.0485 (9)
C20.2614 (3)0.3788 (2)0.42840 (18)0.0494 (9)
C30.2546 (3)0.2798 (2)0.4715 (2)0.0667 (11)
C40.1926 (4)0.1962 (2)0.4261 (2)0.0837 (14)
C50.1397 (4)0.2076 (3)0.3387 (2)0.0833 (16)
C60.1482 (3)0.3040 (2)0.29456 (19)0.0675 (11)
C70.2094 (3)0.39175 (19)0.33964 (18)0.0500 (10)
C80.2207 (3)0.4941 (2)0.29680 (17)0.0520 (9)
C90.2803 (2)0.57833 (19)0.33756 (16)0.0420 (8)
C100.2922 (3)0.68419 (19)0.29424 (16)0.0440 (9)
C110.2102 (3)0.7688 (2)0.32553 (17)0.0512 (10)
C120.2214 (3)0.8674 (2)0.28522 (19)0.0600 (11)
C130.3148 (3)0.8789 (2)0.21205 (19)0.0574 (10)
C140.3970 (3)0.7960 (2)0.17858 (18)0.0598 (11)
C150.3843 (3)0.6977 (2)0.21980 (17)0.0552 (10)
C160.4029 (3)0.6318 (2)0.48920 (17)0.0491 (9)
C170.4389 (3)0.7432 (2)0.47754 (19)0.0538 (10)
C180.3987 (3)0.8269 (2)0.5256 (2)0.0627 (11)
C190.4689 (4)0.9155 (3)0.4879 (2)0.0837 (14)
C200.5505 (4)0.8809 (3)0.4193 (3)0.0800 (14)
H30.291700.271100.530300.0800*
H40.186100.130600.454900.1000*
H50.097800.149700.309000.1000*
H60.113500.310900.235100.0810*
H80.184600.501900.237700.0620*
H110.146300.759400.374700.0610*
H120.166900.924600.307100.0720*
H140.460200.805800.129100.0720*
H150.438100.640500.197300.0660*
H180.335200.826900.575500.0750*
H190.459800.985400.507400.1010*
H200.609400.923500.382200.0960*
U11U22U33U12U13U23
Cl10.0975 (6)0.0700 (5)0.1137 (7)−0.0069 (5)0.0076 (5)0.0403 (6)
O10.0635 (12)0.0737 (15)0.0768 (14)−0.0078 (11)0.0015 (12)−0.0030 (13)
N10.0512 (13)0.0416 (12)0.0374 (11)−0.0028 (11)−0.0005 (11)−0.0017 (11)
N20.0728 (15)0.0637 (16)0.0455 (14)0.0032 (13)−0.0107 (12)−0.0025 (14)
N30.0732 (15)0.0575 (16)0.0457 (13)0.0034 (12)−0.0032 (12)0.0029 (12)
C10.0557 (17)0.0445 (16)0.0453 (16)0.0088 (13)0.0062 (15)0.0033 (14)
C20.0567 (17)0.0442 (16)0.0472 (16)0.0006 (13)0.0102 (14)0.0012 (15)
C30.080 (2)0.0570 (19)0.0632 (19)−0.0034 (15)0.0079 (17)0.0130 (18)
C40.109 (3)0.054 (2)0.088 (2)−0.0159 (19)0.010 (2)0.010 (2)
C50.104 (3)0.054 (2)0.092 (3)−0.0220 (19)−0.002 (2)−0.011 (2)
C60.076 (2)0.060 (2)0.0665 (19)−0.0110 (17)−0.0065 (17)−0.0052 (18)
C70.0521 (17)0.0433 (16)0.0547 (18)−0.0020 (13)0.0042 (14)−0.0043 (15)
C80.0570 (16)0.0545 (17)0.0444 (16)0.0003 (14)−0.0038 (13)−0.0045 (15)
C90.0442 (14)0.0477 (16)0.0341 (14)0.0027 (12)0.0006 (12)−0.0005 (14)
C100.0465 (15)0.0498 (16)0.0358 (14)−0.0018 (13)−0.0030 (13)0.0016 (13)
C110.0491 (17)0.0550 (17)0.0495 (16)0.0003 (13)0.0083 (13)0.0052 (15)
C120.0600 (18)0.0530 (18)0.067 (2)0.0057 (14)0.0012 (16)0.0066 (16)
C130.0597 (18)0.0538 (17)0.0587 (18)−0.0109 (16)−0.0070 (16)0.0193 (16)
C140.0611 (19)0.067 (2)0.0513 (17)−0.0080 (15)0.0113 (14)0.0033 (17)
C150.0623 (17)0.0530 (18)0.0504 (16)−0.0013 (14)0.0093 (15)−0.0030 (15)
C160.0546 (16)0.0521 (17)0.0407 (16)0.0045 (14)−0.0016 (13)−0.0055 (15)
C170.0525 (17)0.0586 (19)0.0502 (18)−0.0028 (15)−0.0081 (15)0.0001 (17)
C180.0672 (19)0.0539 (18)0.0670 (19)0.0022 (16)0.0031 (16)−0.0094 (17)
C190.088 (2)0.060 (2)0.103 (3)0.000 (2)−0.018 (2)−0.018 (2)
C200.073 (2)0.064 (2)0.103 (3)−0.0245 (19)−0.019 (2)0.016 (2)
Cl1—C131.742 (3)C11—C121.380 (4)
O1—C171.362 (3)C12—C131.371 (4)
O1—C201.388 (4)C13—C141.372 (4)
N1—C11.375 (3)C14—C151.383 (4)
N1—C91.419 (3)C16—C171.451 (4)
N1—C161.376 (3)C17—C181.319 (4)
N2—N31.386 (3)C18—C191.398 (4)
N2—C161.308 (3)C19—C201.320 (5)
N3—C11.325 (3)C3—H30.9300
C1—C21.432 (4)C4—H40.9300
C2—C31.400 (4)C5—H50.9300
C2—C71.392 (4)C6—H60.9300
C3—C41.366 (4)C8—H80.9300
C4—C51.374 (4)C11—H110.9300
C5—C61.378 (4)C12—H120.9300
C6—C71.402 (4)C14—H140.9300
C7—C81.438 (4)C15—H150.9300
C8—C91.332 (3)C18—H180.9300
C9—C101.481 (3)C19—H190.9300
C10—C111.377 (4)C20—H200.9300
C10—C151.382 (4)
Cl1···C18i3.579 (3)C16···C113.428 (4)
Cl1···C16ii3.634 (3)C17···C113.053 (4)
Cl1···N1ii3.378 (2)C17···C103.084 (4)
Cl1···C9ii3.634 (2)C18···Cl1viii3.579 (3)
Cl1···H18i2.9000C18···C113.467 (4)
O1···N13.184 (3)C19···C1v3.562 (5)
O1···C102.992 (3)C20···C16v3.456 (5)
O1···C113.192 (3)C20···C123.565 (5)
O1···C153.247 (3)C20···C1v3.483 (5)
N1···O13.184 (3)C2···H14iii2.8100
N1···N22.201 (3)C3···H14iii2.9800
N1···Cl1iii3.378 (2)C8···H153.0600
N2···N12.201 (3)C14···H3vii2.8900
N3···N12.214 (3)C15···H83.0700
N2···H6iv2.8600C17···H113.0500
N2···H11v2.9400C17···H11v2.8600
N2···H12v2.8400C18···H11v2.8800
N2···H8iv2.9200H3···N32.7500
N3···H32.7500H3···C14iv2.8900
N3···H8iv2.7300H6···H82.4900
N3···H20vi2.8800H6···N2vii2.8600
C1···C19vi3.562 (5)H8···C153.0700
C1···C20vi3.483 (5)H8···H62.4900
C3···C14iv3.462 (4)H8···N2vii2.9200
C9···Cl1iii3.634 (2)H8···N3vii2.7300
C10···C173.084 (4)H11···C173.0500
C10···O12.992 (3)H11···N2vi2.9400
C11···O13.192 (3)H11···C17vi2.8600
C11···C173.053 (4)H11···C18vi2.8800
C11···C183.467 (4)H12···N2vi2.8400
C11···C163.428 (4)H14···C2ii2.8100
C12···C203.565 (5)H14···C3ii2.9800
C14···C3vii3.462 (4)H15···C83.0600
C15···O13.247 (3)H18···Cl1viii2.9000
C16···Cl1iii3.634 (3)H20···N3v2.8800
C16···C20vi3.456 (5)
C17—O1—C20104.9 (2)N1—C16—N2110.2 (2)
C1—N1—C9121.46 (19)N1—C16—C17127.8 (2)
C1—N1—C16104.7 (2)N2—C16—C17122.0 (2)
C9—N1—C16133.9 (2)O1—C17—C16118.9 (2)
N3—N2—C16108.1 (2)O1—C17—C18110.5 (2)
N2—N3—C1106.9 (2)C16—C17—C18130.5 (3)
N1—C1—N3110.2 (2)C17—C18—C19107.7 (3)
N1—C1—C2120.8 (2)C18—C19—C20106.9 (3)
N3—C1—C2129.0 (2)O1—C20—C19110.1 (3)
C1—C2—C3121.8 (2)C2—C3—H3120.00
C1—C2—C7117.5 (2)C4—C3—H3120.00
C3—C2—C7120.7 (2)C3—C4—H4119.00
C2—C3—C4119.1 (3)C5—C4—H4120.00
C3—C4—C5121.0 (3)C4—C5—H5120.00
C4—C5—C6120.7 (3)C6—C5—H5120.00
C5—C6—C7119.8 (3)C5—C6—H6120.00
C2—C7—C6118.7 (2)C7—C6—H6120.00
C2—C7—C8119.3 (2)C7—C8—H8118.00
C6—C7—C8122.0 (2)C9—C8—H8118.00
C7—C8—C9123.3 (2)C10—C11—H11120.00
N1—C9—C8117.7 (2)C12—C11—H11119.00
N1—C9—C10118.6 (2)C11—C12—H12121.00
C8—C9—C10123.7 (2)C13—C12—H12121.00
C9—C10—C11121.1 (2)C13—C14—H14121.00
C9—C10—C15119.5 (2)C15—C14—H14121.00
C11—C10—C15119.4 (2)C10—C15—H15120.00
C10—C11—C12121.1 (2)C14—C15—H15120.00
C11—C12—C13118.3 (2)C17—C18—H18126.00
Cl1—C13—C12119.1 (2)C19—C18—H18126.00
Cl1—C13—C14118.8 (2)C18—C19—H19127.00
C12—C13—C14122.1 (2)C20—C19—H19127.00
C13—C14—C15118.8 (2)O1—C20—H20125.00
C10—C15—C14120.3 (2)C19—C20—H20125.00
C20—O1—C17—C16−177.9 (3)C3—C4—C5—C60.1 (5)
C20—O1—C17—C18−1.2 (3)C4—C5—C6—C7−0.9 (5)
C17—O1—C20—C190.6 (4)C5—C6—C7—C20.5 (4)
C9—N1—C1—N3−178.9 (2)C5—C6—C7—C8−179.9 (3)
C9—N1—C1—C21.9 (4)C2—C7—C8—C90.7 (4)
C16—N1—C1—N31.2 (3)C6—C7—C8—C9−179.0 (3)
C16—N1—C1—C2−178.0 (2)C7—C8—C9—N1−0.3 (4)
C1—N1—C9—C8−1.0 (3)C7—C8—C9—C10−179.8 (2)
C1—N1—C9—C10178.6 (2)N1—C9—C10—C11−67.9 (3)
C16—N1—C9—C8178.8 (3)N1—C9—C10—C15113.7 (3)
C16—N1—C9—C10−1.6 (4)C8—C9—C10—C11111.7 (3)
C1—N1—C16—N2−1.0 (3)C8—C9—C10—C15−66.7 (3)
C1—N1—C16—C17−178.7 (3)C9—C10—C11—C12179.9 (2)
C9—N1—C16—N2179.1 (2)C15—C10—C11—C12−1.7 (4)
C9—N1—C16—C171.4 (4)C9—C10—C15—C14−179.9 (2)
C16—N2—N3—C10.4 (3)C11—C10—C15—C141.7 (4)
N3—N2—C16—N10.4 (3)C10—C11—C12—C131.0 (4)
N3—N2—C16—C17178.3 (2)C11—C12—C13—Cl1−179.7 (2)
N2—N3—C1—N1−1.0 (3)C11—C12—C13—C14−0.3 (4)
N2—N3—C1—C2178.2 (3)Cl1—C13—C14—C15179.7 (2)
N1—C1—C2—C3177.6 (2)C12—C13—C14—C150.4 (4)
N1—C1—C2—C7−1.4 (4)C13—C14—C15—C10−1.1 (4)
N3—C1—C2—C3−1.5 (5)N1—C16—C17—O1−62.7 (4)
N3—C1—C2—C7179.5 (3)N1—C16—C17—C18121.5 (3)
C1—C2—C3—C4179.4 (3)N2—C16—C17—O1119.9 (3)
C7—C2—C3—C4−1.7 (4)N2—C16—C17—C18−56.0 (4)
C1—C2—C7—C6179.8 (2)O1—C17—C18—C191.4 (3)
C1—C2—C7—C80.2 (4)C16—C17—C18—C19177.5 (3)
C3—C2—C7—C60.8 (4)C17—C18—C19—C20−0.9 (4)
C3—C2—C7—C8−178.8 (3)C18—C19—C20—O10.2 (4)
C2—C3—C4—C51.2 (5)
D—H···AD—HH···AD···AD—H···A
C20—H20···Cg2v0.932.953.273 (4)102
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the N1–N3/C1/C16 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C20—H20⋯Cg2i0.932.953.273 (4)102

Symmetry code: (i) .

  2 in total

1.  A short history of SHELX.

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

2.  5-Phenyl-3-(2-thien-yl)-1,2,4-triazolo[3,4-a]isoquinoline.

Authors:  F Nawaz Khan; P Manivel; K Prabakaran; Venkatesha R Hathwar; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-30
  2 in total

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