Literature DB >> 21587791

3-[(2-Chloro-6-methyl-quinolin-3-yl)meth-yl]quinazolin-4(3H)-one.

S Mohana Roopan, F Nawaz Khan, Sriramakrishnaswamy Kone, Venkatesha R Hathwar, Mehmet Akkurt.   

Abstract

In the title mol-ecule, C(19)H(14)ClN(3)O, the quinoline and quinazoline ring systems form a dihedral angle of 80.75 (4)°. In the crystal, the mol-ecules are linked by pairs of C-H⋯N hydrogen bonds into centrosymmetric dimers, generating R(2) (2)(6) ring motifs. The structure is further stabilized by C-H⋯π inter-actions and π-π stacking inter-actions [centroid-centroid distances = 3.7869 (8) and 3.8490 (8) Å].

Entities:  

Year:  2010        PMID： 21587791      PMCID： PMC3006817          DOI： 10.1107/S1600536810020830

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


Related literature

For quinoline analogues, see: Roopan et al. (2009 ▶); Khan et al. (2009 ▶, 2010a ▶,b ▶). For quinazolinone analogues, see: Roopan et al. (2008a ▶,b ▶). For the properties and applications of related compounds, see: Abdel-Hamide et al. (1996 ▶); Bekhit & Khalil (1998 ▶); Chapman et al. (1963 ▶); Honda et al. (1979 ▶).

Experimental

Crystal data

C19H14ClN3O M = 335.78 Monoclinic, a = 7.86728 (14) Å b = 14.7098 (3) Å c = 13.7055 (3) Å β = 102.1500 (17)° V = 1550.56 (5) Å3 Z = 4 Mo Kα radiation μ = 0.26 mm−1 T = 295 K 0.25 × 0.21 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur E CCD diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.938, T max = 0.960 15755 measured reflections 3048 independent reflections 2417 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.096 S = 1.14 3048 reflections 219 parameters H-atom parameters constrained Δρmax = 0.18 e Å−3 Δρmin = −0.19 e Å−3 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/S1600536810020830/gk2276sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020830/gk2276Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H14ClN3OF(000) = 696
Mr = 335.78Dx = 1.438 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1326 reflections
a = 7.86728 (14) Åθ = 2.0–20.7°
b = 14.7098 (3) ŵ = 0.26 mm−1
c = 13.7055 (3) ÅT = 295 K
β = 102.1500 (17)°Needle, colourless
V = 1550.56 (5) Å30.25 × 0.21 × 0.16 mm
Z = 4
Oxford Diffraction Xcalibur E CCD diffractometer3048 independent reflections
Radiation source: Enhance (Mo) X-ray Source2417 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)h = −9→9
Tmin = 0.938, Tmax = 0.960k = −18→18
15755 measured reflectionsl = −16→16
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.096w = 1/[σ2(Fo2) + (0.0511P)2 + 0.0739P] where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
3048 reflectionsΔρmax = 0.18 e Å−3
219 parametersΔρmin = −0.19 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0123 (15)
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 e.s.d.'s 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
Cl11.05099 (5)0.28142 (3)1.12633 (3)0.0552 (2)
O10.60460 (15)0.24457 (8)0.79970 (8)0.0550 (4)
N10.90795 (14)0.12379 (9)1.13506 (8)0.0409 (4)
N20.82439 (14)0.32871 (8)0.89095 (8)0.0368 (4)
N30.79403 (17)0.48498 (9)0.92418 (9)0.0453 (4)
C10.94294 (18)0.18353 (10)1.07237 (11)0.0389 (5)
C20.90272 (18)0.17726 (10)0.96669 (10)0.0374 (5)
C30.82067 (18)0.09933 (10)0.92894 (10)0.0395 (5)
C40.77799 (17)0.03094 (10)0.99195 (10)0.0366 (4)
C50.69103 (18)−0.05001 (10)0.95563 (11)0.0413 (5)
C60.64859 (18)−0.11435 (10)1.01883 (11)0.0403 (5)
C70.6946 (2)−0.09747 (11)1.12254 (11)0.0461 (5)
C80.77957 (19)−0.02054 (11)1.16013 (11)0.0444 (5)
C90.82367 (17)0.04583 (10)1.09569 (10)0.0373 (5)
C100.5554 (2)−0.20015 (11)0.97943 (13)0.0519 (6)
C110.9436 (2)0.25093 (11)0.89857 (12)0.0442 (5)
C120.65169 (19)0.31653 (10)0.84072 (10)0.0383 (4)
C130.54199 (18)0.39518 (10)0.84513 (10)0.0376 (5)
C140.3617 (2)0.38997 (12)0.80976 (11)0.0497 (6)
C150.2604 (2)0.46424 (15)0.81376 (12)0.0613 (7)
C160.3351 (3)0.54611 (15)0.85043 (13)0.0658 (7)
C170.5113 (2)0.55297 (12)0.88491 (12)0.0571 (6)
C180.61654 (19)0.47690 (10)0.88456 (10)0.0406 (5)
C190.88460 (19)0.41208 (11)0.92637 (11)0.0415 (5)
H30.792200.091000.860200.0470*
H50.66180−0.060000.887100.0500*
H70.66590−0.140201.166400.0550*
H80.80880−0.011701.228800.0530*
H10A0.44010−0.199500.992300.0780*
H10B0.61780−0.251701.011900.0780*
H10C0.54880−0.204200.908800.0780*
H11A1.061700.272000.923300.0530*
H11B0.937300.225600.832500.0530*
H140.311300.335700.783500.0600*
H150.140400.460100.791800.0740*
H160.265000.596800.851600.0790*
H170.560500.608300.908500.0690*
H191.002500.416500.954800.0500*
U11U22U33U12U13U23
Cl10.0554 (3)0.0545 (3)0.0522 (3)−0.0078 (2)0.0032 (2)−0.0056 (2)
O10.0623 (7)0.0417 (7)0.0540 (7)−0.0106 (5)−0.0034 (5)−0.0054 (5)
N10.0375 (7)0.0482 (8)0.0363 (7)0.0036 (6)0.0060 (5)−0.0013 (6)
N20.0353 (6)0.0375 (7)0.0368 (6)−0.0034 (5)0.0059 (5)0.0015 (5)
N30.0483 (8)0.0392 (8)0.0451 (7)−0.0082 (6)0.0021 (6)0.0015 (6)
C10.0316 (7)0.0426 (9)0.0422 (8)0.0051 (6)0.0068 (6)−0.0016 (7)
C20.0347 (8)0.0412 (9)0.0377 (8)0.0094 (6)0.0110 (6)0.0016 (6)
C30.0442 (8)0.0435 (9)0.0320 (7)0.0103 (7)0.0109 (6)−0.0005 (6)
C40.0365 (8)0.0397 (8)0.0347 (7)0.0109 (6)0.0100 (6)0.0001 (6)
C50.0440 (8)0.0446 (9)0.0361 (8)0.0083 (7)0.0105 (6)−0.0042 (7)
C60.0358 (8)0.0401 (9)0.0468 (9)0.0088 (6)0.0128 (6)0.0002 (7)
C70.0449 (9)0.0495 (10)0.0467 (9)0.0038 (7)0.0158 (7)0.0083 (7)
C80.0439 (8)0.0557 (10)0.0341 (8)0.0024 (7)0.0096 (6)0.0028 (7)
C90.0326 (7)0.0436 (9)0.0369 (8)0.0087 (6)0.0099 (6)0.0007 (6)
C100.0519 (10)0.0455 (10)0.0604 (10)0.0026 (8)0.0169 (8)−0.0015 (8)
C110.0436 (9)0.0479 (9)0.0436 (8)0.0035 (7)0.0152 (7)0.0017 (7)
C120.0430 (8)0.0383 (8)0.0317 (7)−0.0078 (7)0.0038 (6)0.0041 (6)
C130.0392 (8)0.0436 (9)0.0293 (7)−0.0041 (7)0.0054 (6)0.0083 (6)
C140.0414 (9)0.0646 (11)0.0400 (9)−0.0059 (8)0.0015 (7)0.0123 (8)
C150.0433 (10)0.0941 (15)0.0460 (10)0.0117 (10)0.0084 (7)0.0210 (10)
C160.0701 (13)0.0799 (14)0.0482 (10)0.0341 (11)0.0143 (9)0.0114 (10)
C170.0739 (12)0.0484 (10)0.0478 (10)0.0125 (9)0.0101 (8)0.0022 (8)
C180.0475 (9)0.0425 (9)0.0318 (7)−0.0007 (7)0.0083 (6)0.0046 (6)
C190.0386 (8)0.0432 (9)0.0402 (8)−0.0114 (7)0.0028 (6)0.0039 (7)
Cl1—C11.7545 (15)C13—C141.401 (2)
O1—C121.2191 (19)C13—C181.396 (2)
N1—C11.2984 (19)C14—C151.360 (3)
N1—C91.3767 (19)C15—C161.387 (3)
N2—C111.469 (2)C16—C171.371 (3)
N2—C121.3994 (19)C17—C181.393 (2)
N2—C191.367 (2)C3—H30.9300
N3—C181.393 (2)C5—H50.9300
N3—C191.284 (2)C7—H70.9300
C1—C21.419 (2)C8—H80.9300
C2—C31.363 (2)C10—H10A0.9600
C2—C111.509 (2)C10—H10B0.9600
C3—C41.412 (2)C10—H10C0.9600
C4—C51.411 (2)C11—H11A0.9700
C4—C91.4084 (19)C11—H11B0.9700
C5—C61.371 (2)C14—H140.9300
C6—C71.413 (2)C15—H150.9300
C6—C101.502 (2)C16—H160.9300
C7—C81.359 (2)C17—H170.9300
C8—C91.408 (2)C19—H190.9300
C12—C131.452 (2)
Cl1···N23.4130 (12)C15···H3ix2.9900
Cl1···C193.3776 (16)C16···H3ix2.9200
Cl1···H11A2.8000C18···H8vi2.9100
Cl1···H193.0400C19···H15x3.0800
Cl1···H16i3.1300C19···H19iv3.0300
Cl1···H11Bii3.1400C19···H8vi3.0300
O1···C23.0757 (18)H3···O12.7300
O1···C33.0535 (18)H3···H52.5100
O1···H32.7300H3···H11B2.3600
O1···H11B2.5800H3···C15xi2.9900
O1···H142.6400H3···C16xi2.9200
O1···H7iii2.7400H5···H32.5100
N2···Cl13.4130 (12)H5···H10C2.3400
N3···C19iv3.271 (2)H5···C14xi2.7700
N1···H15v2.8000H5···C15xi2.9600
N3···H19iv2.5100H7···O1iii2.7400
N3···H8vi2.7300H8···N3ii2.7300
C1···C5vii3.573 (2)H8···C18ii2.9100
C2···O13.0757 (18)H8···C19ii3.0300
C3···O13.0535 (18)H10A···C1iii2.9700
C3···C9vii3.592 (2)H10A···C2iii2.8900
C3···C123.572 (2)H10A···C3iii2.9100
C4···C4vii3.5715 (19)H10A···C4iii3.0500
C4···C6iii3.547 (2)H10A···C12iii3.0700
C5···C1vii3.572 (2)H10B···H17viii2.4900
C6···C4iii3.547 (2)H10B···H11Avii2.5100
C9···C3vii3.592 (2)H10C···H52.3400
C12···C33.572 (2)H11A···Cl12.8000
C16···C18i3.587 (2)H11A···H192.2400
C17···C18i3.539 (2)H11A···H10Bvii2.5100
C17···C17i3.557 (2)H11B···O12.5800
C18···C17i3.539 (2)H11B···H32.3600
C18···C16i3.587 (2)H11B···Cl1vi3.1400
C19···N3iv3.271 (2)H14···O12.6400
C19···Cl13.3776 (16)H15···C19xii3.0800
C19···C19iv3.538 (2)H15···N1xiii2.8000
C1···H10Aiii2.9700H16···Cl1i3.1300
C2···H10Aiii2.8900H17···C10xiv2.9800
C3···H10Aiii2.9100H17···H10Bxiv2.4900
C4···H10Aiii3.0500H19···Cl13.0400
C10···H17viii2.9800H19···H11A2.2400
C12···H10Aiii3.0700H19···N3iv2.5100
C14···H5ix2.7700H19···C19iv3.0300
C15···H5ix2.9600
C1—N1—C9117.14 (12)C16—C17—C18119.90 (17)
C11—N2—C12118.32 (12)N3—C18—C13121.98 (13)
C11—N2—C19120.35 (12)N3—C18—C17118.56 (14)
C12—N2—C19121.18 (12)C13—C18—C17119.46 (14)
C18—N3—C19116.34 (13)N2—C19—N3126.29 (14)
Cl1—C1—N1115.34 (11)C2—C3—H3119.00
Cl1—C1—C2117.89 (11)C4—C3—H3119.00
N1—C1—C2126.78 (14)C4—C5—H5119.00
C1—C2—C3115.35 (13)C6—C5—H5119.00
C1—C2—C11123.66 (13)C6—C7—H7119.00
C3—C2—C11120.99 (13)C8—C7—H7119.00
C2—C3—C4121.45 (13)C7—C8—H8120.00
C3—C4—C5123.08 (13)C9—C8—H8120.00
C3—C4—C9117.63 (13)C6—C10—H10A110.00
C5—C4—C9119.29 (13)C6—C10—H10B109.00
C4—C5—C6121.62 (13)C6—C10—H10C109.00
C5—C6—C7118.00 (14)H10A—C10—H10B109.00
C5—C6—C10121.23 (14)H10A—C10—H10C109.00
C7—C6—C10120.78 (14)H10B—C10—H10C109.00
C6—C7—C8121.94 (14)N2—C11—H11A109.00
C7—C8—C9120.39 (14)N2—C11—H11B109.00
N1—C9—C4121.65 (13)C2—C11—H11A109.00
N1—C9—C8119.58 (12)C2—C11—H11B109.00
C4—C9—C8118.76 (13)H11A—C11—H11B108.00
N2—C11—C2112.79 (12)C13—C14—H14120.00
O1—C12—N2120.49 (14)C15—C14—H14120.00
O1—C12—C13125.83 (14)C14—C15—H15120.00
N2—C12—C13113.67 (12)C16—C15—H15120.00
C12—C13—C14120.61 (14)C15—C16—H16120.00
C12—C13—C18119.82 (13)C17—C16—H16120.00
C14—C13—C18119.57 (14)C16—C17—H17120.00
C13—C14—C15120.08 (16)C18—C17—H17120.00
C14—C15—C16120.32 (17)N2—C19—H19117.00
C15—C16—C17120.62 (19)N3—C19—H19117.00
C9—N1—C1—Cl1−179.80 (10)C3—C4—C9—N1−0.4 (2)
C9—N1—C1—C20.3 (2)C3—C4—C9—C8178.79 (13)
C1—N1—C9—C40.4 (2)C5—C4—C9—N1−179.72 (13)
C1—N1—C9—C8−178.82 (13)C5—C4—C9—C8−0.5 (2)
C12—N2—C11—C2−69.62 (16)C4—C5—C6—C70.0 (2)
C19—N2—C11—C2114.68 (14)C4—C5—C6—C10179.76 (14)
C11—N2—C12—O1−4.0 (2)C5—C6—C7—C8−0.5 (2)
C11—N2—C12—C13174.94 (12)C10—C6—C7—C8179.74 (15)
C19—N2—C12—O1171.64 (13)C6—C7—C8—C90.5 (2)
C19—N2—C12—C13−9.40 (18)C7—C8—C9—N1179.26 (14)
C11—N2—C19—N3−179.97 (14)C7—C8—C9—C40.1 (2)
C12—N2—C19—N34.5 (2)O1—C12—C13—C147.1 (2)
C19—N3—C18—C13−2.9 (2)O1—C12—C13—C18−172.61 (14)
C19—N3—C18—C17176.95 (14)N2—C12—C13—C14−171.76 (13)
C18—N3—C19—N22.1 (2)N2—C12—C13—C188.50 (19)
Cl1—C1—C2—C3179.26 (11)C12—C13—C14—C15−179.62 (14)
Cl1—C1—C2—C11−1.6 (2)C18—C13—C14—C150.1 (2)
N1—C1—C2—C3−0.8 (2)C12—C13—C18—N3−2.7 (2)
N1—C1—C2—C11178.31 (14)C12—C13—C18—C17177.48 (13)
C1—C2—C3—C40.7 (2)C14—C13—C18—N3177.54 (13)
C11—C2—C3—C4−178.43 (14)C14—C13—C18—C17−2.3 (2)
C1—C2—C11—N2−75.60 (18)C13—C14—C15—C161.7 (2)
C3—C2—C11—N2103.49 (16)C14—C15—C16—C17−1.3 (3)
C2—C3—C4—C5179.10 (14)C15—C16—C17—C18−0.9 (3)
C2—C3—C4—C9−0.2 (2)C16—C17—C18—N3−177.16 (15)
C3—C4—C5—C6−178.76 (14)C16—C17—C18—C132.7 (2)
C9—C4—C5—C60.5 (2)
Cg1 and Cg2 are the centroids of the N1/C1–C4/C9 and N2/N3/C12/C13/C18/C19 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C19—H19···N3iv0.932.513.271 (2)139
C8—H8···Cg2ii0.932.893.6598 (16)142
C10—H10A···Cg1iii0.962.683.5189 (17)146
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1–C4/C9 and N2/N3/C12/C13/C18/C19 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C19—H19⋯N3i0.932.513.271 (2)139
C8—H8⋯Cg2ii0.932.893.6598 (16)142
C10—H10A⋯Cg1iii0.962.683.5189 (17)146

Symmetry codes: (i) ; (ii) ; (iii) .

  6 in total

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

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Authors:  G Honda; M Tabata; M Tsuda
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Authors:  F Nawaz Khan; S Mohana Roopan; Venkatesha R Hathwar; Seik Weng Ng
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4.  2-Chloro-3-hydroxy-methyl-6-methoxy-quinoline.

Authors:  F Nawaz Khan; S Mohana Roopan; Venkatesha R Hathwar; Seik Weng Ng
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5.  Non-steroidal anti-inflammatory agents: synthesis of novel benzopyrazolyl, benzoxazolyl and quinazolinyl derivatives of 4(3 H)-quinazolinones.

Authors:  A A Bekhit; M A Khalil
Journal:  Pharmazie       Date:  1998-08       Impact factor: 1.267

6.  2-Chloro-6-methyl-quinoline-3-carbaldehyde.

Authors:  F Nawaz Khan; R Subashini; S Mohana Roopan; Venkatesha R Hathwar; Seik Weng Ng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-10
  6 in total

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