Literature DB >> 21588661

5,8-Dimeth-oxy-2-phenyl-1,4-dihydro-quinoline-3-carbonitrile.

Souheila Ladraa, Abdelmalek Bouraiou, Sofiane Bouacida, Thierry Roisnel, Ali Belfaitah.   

Abstract

The crystal structure of the title mol-ecule, C(18)H(16)N(2)O(2), can be described as two types of crossed layers parallel to the (110) and (10) planes. An intra-molecular N-H⋯O hydrogen bond occurs.

Entities:  

Year:  2010        PMID： 21588661      PMCID： PMC3008076          DOI： 10.1107/S1600536810031685

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


Related literature

For our previous work on the preparation of quinoline derivatives see: Benzerka et al. (2008 ▶); Ladraa et al. (2009 ▶, 2010 ▶); Moussaoui et al. (2002 ▶); Menasra et al. (2005 ▶); Belfaitah et al. (2006 ▶); Bouraiou et al. (2006 ▶, 2007 ▶, 2008 ▶). For more details of quinoline reduction, see: Dauphinee & Forrest (1978 ▶); Srikrishna et al. (1996 ▶); Vierhapper & Eliel (1975 ▶); Lim et al. (1995 ▶).

Experimental

Crystal data

C18H16N2O2 M = 292.33 Monoclinic, a = 3.9952 (3) Å b = 20.4544 (15) Å c = 17.7313 (13) Å β = 95.976 (5)° V = 1441.12 (18) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 150 K 0.27 × 0.07 × 0.05 mm

Data collection

Bruker APEXII diffractometer Absorption correction: multi-scan (SADABS: Sheldrick, 2002 ▶) T min = 0.702, T max = 0.996 12491 measured reflections 3292 independent reflections 1975 reflections with I > 2σ(I) R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.133 S = 1.03 3292 reflections 201 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.29 e Å−3 Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031685/hg2695sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031685/hg2695Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H16N2O2F(000) = 616
Mr = 292.33Dx = 1.347 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2693 reflections
a = 3.9952 (3) Åθ = 2.3–25.3°
b = 20.4544 (15) ŵ = 0.09 mm−1
c = 17.7313 (13) ÅT = 150 K
β = 95.976 (5)°Stick, colourless
V = 1441.12 (18) Å30.27 × 0.07 × 0.05 mm
Z = 4
Bruker APEXII diffractometer1975 reflections with I > 2σ(I)
graphiteRint = 0.051
CCD rotation images, thin slices scansθmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS: Sheldrick, 2002)h = −3→5
Tmin = 0.702, Tmax = 0.996k = −26→24
12491 measured reflectionsl = −22→22
3292 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0462P)2 + 0.6371P] where P = (Fo2 + 2Fc2)/3
3292 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.29 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
C10.1215 (5)0.13620 (9)0.66975 (11)0.0267 (5)
C20.0694 (5)0.18185 (9)0.72449 (11)0.0252 (4)
C30.2040 (5)0.17402 (10)0.80517 (11)0.0302 (5)
H3A0.01480.17630.83700.036*
H3B0.35730.21100.81980.036*
C40.3890 (5)0.11164 (9)0.82153 (11)0.0258 (4)
C50.5299 (5)0.09642 (10)0.89555 (11)0.0280 (5)
C60.7054 (5)0.03884 (10)0.91013 (12)0.0329 (5)
H60.79930.02890.96030.040*
C70.7448 (5)−0.00496 (10)0.85068 (12)0.0329 (5)
H70.8668−0.04440.86090.040*
C80.6090 (5)0.00849 (9)0.77773 (11)0.0282 (5)
C100.8195 (6)−0.09023 (10)0.72813 (14)0.0402 (6)
H10A1.0483−0.08070.75090.060*
H10B0.8296−0.11300.67980.060*
H10C0.7053−0.11800.76260.060*
C110.6472 (6)0.13355 (11)1.02389 (11)0.0377 (5)
H11A0.56990.09261.04500.056*
H11B0.59630.17011.05660.056*
H11C0.89060.13131.02110.056*
C12−0.1237 (5)0.23988 (10)0.70655 (11)0.0273 (5)
C130.0034 (5)0.14369 (9)0.58792 (11)0.0268 (4)
C140.0519 (5)0.20237 (10)0.55075 (11)0.0319 (5)
H140.16070.23780.57790.038*
C15−0.0572 (6)0.20951 (11)0.47439 (12)0.0383 (6)
H15−0.02320.24980.44960.046*
C16−0.2153 (6)0.15839 (12)0.43412 (13)0.0419 (6)
H16−0.29280.16370.38200.050*
C17−0.2606 (6)0.09925 (12)0.46989 (12)0.0409 (6)
H17−0.36700.06390.44210.049*
C18−0.1503 (5)0.09145 (11)0.54663 (12)0.0347 (5)
H18−0.17940.05070.57090.042*
C90.4271 (5)0.06718 (9)0.76313 (11)0.0265 (4)
N10.2916 (4)0.07985 (8)0.68900 (9)0.0294 (4)
H10.31660.05060.65360.035*
N2−0.2790 (5)0.28731 (9)0.69710 (10)0.0370 (5)
O10.6360 (4)−0.02995 (7)0.71508 (8)0.0351 (4)
O20.4784 (4)0.14325 (7)0.94924 (8)0.0337 (4)
U11U22U33U12U13U23
C10.0277 (11)0.0253 (11)0.0271 (11)−0.0058 (8)0.0032 (8)0.0022 (8)
C20.0292 (11)0.0213 (10)0.0250 (10)−0.0039 (8)0.0028 (8)0.0011 (8)
C30.0297 (11)0.0285 (11)0.0324 (11)−0.0049 (9)0.0028 (9)0.0070 (9)
C40.0272 (11)0.0220 (10)0.0287 (11)−0.0034 (8)0.0052 (8)0.0045 (8)
C50.0298 (11)0.0280 (11)0.0262 (11)−0.0047 (8)0.0029 (8)0.0023 (8)
C60.0361 (13)0.0304 (12)0.0318 (12)−0.0007 (9)0.0007 (9)0.0089 (9)
C70.0331 (12)0.0252 (11)0.0407 (13)0.0033 (9)0.0047 (9)0.0083 (9)
C80.0294 (11)0.0226 (10)0.0335 (11)−0.0027 (8)0.0070 (8)0.0023 (8)
C100.0401 (14)0.0264 (12)0.0548 (15)0.0061 (10)0.0088 (11)−0.0030 (10)
C110.0463 (14)0.0409 (13)0.0245 (11)−0.0055 (10)−0.0022 (9)0.0027 (9)
C120.0341 (12)0.0240 (11)0.0240 (10)−0.0047 (9)0.0044 (8)−0.0027 (8)
C130.0271 (11)0.0275 (11)0.0258 (11)0.0017 (8)0.0033 (8)−0.0019 (8)
C140.0389 (13)0.0288 (11)0.0287 (11)0.0025 (9)0.0061 (9)0.0010 (9)
C150.0514 (15)0.0366 (13)0.0279 (12)0.0090 (11)0.0092 (10)0.0048 (9)
C160.0462 (15)0.0560 (16)0.0233 (11)0.0130 (12)0.0022 (10)−0.0021 (10)
C170.0403 (14)0.0482 (15)0.0332 (12)0.0000 (11)−0.0009 (10)−0.0140 (11)
C180.0380 (13)0.0311 (12)0.0347 (12)−0.0034 (9)0.0030 (9)−0.0031 (9)
C90.0262 (11)0.0225 (10)0.0309 (11)−0.0038 (8)0.0043 (8)0.0050 (8)
N10.0406 (11)0.0229 (9)0.0246 (9)0.0000 (7)0.0025 (7)0.0010 (7)
N20.0475 (12)0.0287 (10)0.0348 (10)0.0044 (9)0.0045 (8)−0.0014 (8)
O10.0422 (9)0.0258 (8)0.0378 (9)0.0044 (6)0.0071 (7)−0.0003 (6)
O20.0436 (9)0.0320 (8)0.0244 (8)0.0003 (6)−0.0019 (6)0.0000 (6)
C1—N11.363 (3)C10—H10B0.9800
C1—C21.378 (3)C10—H10C0.9800
C1—C131.486 (3)C11—O21.435 (2)
C2—C121.433 (3)C11—H11A0.9800
C2—C31.484 (3)C11—H11B0.9800
C3—C41.488 (3)C11—H11C0.9800
C3—H3A0.9900C12—N21.154 (3)
C3—H3B0.9900C13—C141.393 (3)
C4—C91.398 (3)C13—C181.400 (3)
C4—C51.408 (3)C14—C151.386 (3)
C5—O21.381 (2)C14—H140.9500
C5—C61.381 (3)C15—C161.381 (3)
C6—C71.405 (3)C15—H150.9500
C6—H60.9500C16—C171.386 (3)
C7—C81.377 (3)C16—H160.9500
C7—H70.9500C17—C181.395 (3)
C8—O11.374 (2)C17—H170.9500
C8—C91.413 (3)C18—H180.9500
C10—O11.441 (2)C9—N11.393 (2)
C10—H10A0.9800N1—H10.8800
N1—C1—C2120.29 (17)O2—C11—H11A109.5
N1—C1—C13115.53 (17)O2—C11—H11B109.5
C2—C1—C13124.18 (18)H11A—C11—H11B109.5
C1—C2—C12121.48 (17)O2—C11—H11C109.5
C1—C2—C3122.67 (18)H11A—C11—H11C109.5
C12—C2—C3115.85 (17)H11B—C11—H11C109.5
C2—C3—C4113.79 (17)N2—C12—C2175.5 (2)
C2—C3—H3A108.8C14—C13—C18119.03 (19)
C4—C3—H3A108.8C14—C13—C1120.34 (17)
C2—C3—H3B108.8C18—C13—C1120.61 (18)
C4—C3—H3B108.8C15—C14—C13120.5 (2)
H3A—C3—H3B107.7C15—C14—H14119.7
C9—C4—C5118.87 (18)C13—C14—H14119.7
C9—C4—C3120.23 (17)C16—C15—C14120.4 (2)
C5—C4—C3120.90 (18)C16—C15—H15119.8
O2—C5—C6124.87 (17)C14—C15—H15119.8
O2—C5—C4114.55 (17)C15—C16—C17119.9 (2)
C6—C5—C4120.58 (19)C15—C16—H16120.1
C5—C6—C7119.86 (19)C17—C16—H16120.1
C5—C6—H6120.1C16—C17—C18120.2 (2)
C7—C6—H6120.1C16—C17—H17119.9
C8—C7—C6120.88 (19)C18—C17—H17119.9
C8—C7—H7119.6C17—C18—C13120.0 (2)
C6—C7—H7119.6C17—C18—H18120.0
O1—C8—C7126.04 (18)C13—C18—H18120.0
O1—C8—C9114.84 (17)N1—C9—C4121.09 (17)
C7—C8—C9119.11 (19)N1—C9—C8118.22 (18)
O1—C10—H10A109.5C4—C9—C8120.68 (18)
O1—C10—H10B109.5C1—N1—C9121.88 (17)
H10A—C10—H10B109.5C1—N1—H1119.1
O1—C10—H10C109.5C9—N1—H1119.1
H10A—C10—H10C109.5C8—O1—C10116.18 (16)
H10B—C10—H10C109.5C5—O2—C11116.77 (16)
N1—C1—C2—C12−176.67 (19)C13—C14—C15—C16−0.1 (3)
C13—C1—C2—C123.5 (3)C14—C15—C16—C17−1.0 (3)
N1—C1—C2—C32.6 (3)C15—C16—C17—C180.7 (3)
C13—C1—C2—C3−177.25 (19)C16—C17—C18—C130.7 (3)
C1—C2—C3—C4−2.0 (3)C14—C13—C18—C17−1.8 (3)
C12—C2—C3—C4177.34 (17)C1—C13—C18—C17179.85 (19)
C2—C3—C4—C90.9 (3)C5—C4—C9—N1179.80 (18)
C2—C3—C4—C5−179.41 (18)C3—C4—C9—N1−0.5 (3)
C9—C4—C5—O2−179.88 (16)C5—C4—C9—C8−1.2 (3)
C3—C4—C5—O20.4 (3)C3—C4—C9—C8178.53 (19)
C9—C4—C5—C60.6 (3)O1—C8—C9—N10.9 (3)
C3—C4—C5—C6−179.07 (19)C7—C8—C9—N1−179.98 (18)
O2—C5—C6—C7−179.32 (19)O1—C8—C9—C4−178.15 (17)
C4—C5—C6—C70.1 (3)C7—C8—C9—C41.0 (3)
C5—C6—C7—C8−0.3 (3)C2—C1—N1—C9−2.1 (3)
C6—C7—C8—O1178.81 (19)C13—C1—N1—C9177.77 (17)
C6—C7—C8—C9−0.2 (3)C4—C9—N1—C11.1 (3)
N1—C1—C13—C14−133.8 (2)C8—C9—N1—C1−178.01 (18)
C2—C1—C13—C1446.0 (3)C7—C8—O1—C101.1 (3)
N1—C1—C13—C1844.5 (3)C9—C8—O1—C10−179.86 (18)
C2—C1—C13—C18−135.6 (2)C6—C5—O2—C116.0 (3)
C18—C13—C14—C151.5 (3)C4—C5—O2—C11−173.46 (18)
C1—C13—C14—C15179.86 (19)
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.882.292.649 (2)104
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O10.882.292.649 (2)104
  4 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.  2-Chloro-quinoline-3-carboxylic acid.

Authors:  Souheila Ladraa; Abdelmalek Bouraiou; Sofiane Bouacida; Thierry Roisnel; Ali Belfaitah
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-27

3.  The diastereoisomers 2-[(S/R)-2-chloro-3-quinolyl]-2-[(R)-1-(4-methoxyphenyl)ethylamino]acetonitrile at 100 K.

Authors:  Souheila Ladraa; Abdelmalek Bouraiou; Sofiane Bouacida; Thierry Roisnel; Ali Belfaitah
Journal:  Acta Crystallogr C       Date:  2009-08-22       Impact factor: 1.172

4.  (3RS,4SR)-Methyl 4-(2-chloro-5,8-di-methoxy-quinolin-3-yl)-1-phenyl-pyrrolidine-3-carboxyl-ate.

Authors:  Saida Benzerka; Abdelmalek Bouraiou; Sofiane Bouacida; Salah Rhouati; Ali Belfaitah
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-09
  4 in total
  1 in total

1.  2-(2-Chloro-6,7-dimethyl-quinolin-3-yl)-2,3-dihydro-quinolin-4(1H)-one.

Authors:  Saida Benzerka; Abdelmalek Bouraiou; Sofiane Bouacida; Thierry Roisnel; Ali Belfaitah
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-23
  1 in total

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