Literature DB >> 23476426

Ethyl 2,7,7-trimethyl-4-(1-methyl-1H-indol-3-yl)-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

Sema Oztürk Yildirim1, Ray J Butcher, Miyase Gözde Gündüz, Ahmed El-Khouly, Rahime Simşek, Cihat Safak.   

Abstract

In the title mol-ecule, C24H28N2O3, the n class="Chemical">cyclo-hexene ring is in a sofa conformation and the 1,4-dihydro-pyridine ring is in a slight boat conformation. In the indole ring system, the pyrrole and benzene rings form a dihedral angle of 2.63 (7)°. In the crystal, N-H⋯O hydrogen bonds connect the mol-ecules into C(6) chains parallel to the b axis and pairs of weak C-H⋯O hydrogen bonds link inversion-related chains into a ladder motif through R2(2)(18) rings. A weak intra-molecular C-H⋯O hydrogen bond is also observed.

Entities:  

Year:  2012        PMID: 23476426      PMCID: PMC3588325          DOI: 10.1107/S1600536812047976

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


Related literature

For the biological functions of calcium ions, see: Triggle & Swamy (1980 ▶) and for the biological functions and physiological roles of n class="Chemical">calcium channels, see: Zamponi (1997 ▶); Dolphin (2006 ▶). For the biological properties of 1,4-dihydro pyridines (DHP), see: Vaghy et al. (1987 ▶); Triggle (2003 ▶); Şafak & Şimşek (2006 ▶); Zhou et al., (2011 ▶). For nifedipine (the prototypical DHP) in clinical use, see: Gordeev et al. (1998 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For similar structures, see: El-Khouly et al. (2012 ▶); Öztürk Yildirim et al. (2012 ▶); Gündüz, et al. (2012 ▶).

Experimental

Crystal data

C24H28N2O3 M = 392.48 Monoclinic, a = 17.4656 (4) Å b = 10.1883 (2) Å c = 12.3465 (3) Å β = 106.806 (2)° V = 2103.16 (8) Å3 Z = 4 Cu Kα radiation μ = 0.65 mm−1 T = 123 K 0.55 × 0.40 × 0.35 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T min = 0.715, T max = 0.804 8035 measured reflections 4246 independent reflections 3533 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.125 S = 1.03 4246 reflections 271 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.27 e Å−3 Δρmin = −0.23 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: SHELXTL; software used to prepare material for publication: SHELXTL. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047976/lh5560sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047976/lh5560Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H28N2O3F(000) = 840
Mr = 392.48Dx = 1.240 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 3252 reflections
a = 17.4656 (4) Åθ = 3.7–75.7°
b = 10.1883 (2) ŵ = 0.65 mm1
c = 12.3465 (3) ÅT = 123 K
β = 106.806 (2)°Block, colorless
V = 2103.16 (8) Å30.55 × 0.40 × 0.35 mm
Z = 4
Agilent Xcalibur (Ruby, Gemini) diffractometer4246 independent reflections
Radiation source: Enhance (Cu) X-ray Source3533 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 10.5081 pixels mm-1θmax = 75.9°, θmin = 5.1°
ω scansh = −20→21
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived from Clark & Reid (1995)]k = −12→10
Tmin = 0.715, Tmax = 0.804l = −14→15
8035 measured 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0707P)2 + 0.4192P] where P = (Fo2 + 2Fc2)/3
4246 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.23 e Å3
Experimental. Absorption correction: CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Clark & Reid, 1995).
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
O10.80036 (6)0.10674 (11)0.14843 (8)0.0291 (2)
O20.50682 (7)0.45404 (15)0.20829 (11)0.0444 (3)
O30.53584 (6)0.31811 (11)0.08329 (9)0.0281 (2)
N10.74838 (7)0.40267 (13)0.41035 (10)0.0250 (3)
N20.70297 (7)0.49919 (13)−0.07455 (10)0.0254 (3)
C10.79738 (8)0.31973 (14)0.37441 (11)0.0235 (3)
C20.87530 (9)0.28770 (16)0.46042 (12)0.0289 (3)
H2A0.86620.21850.51160.035*
H2B0.89520.36680.50660.035*
C30.93922 (9)0.24060 (16)0.40645 (12)0.0301 (3)
C40.90135 (9)0.13072 (16)0.32375 (13)0.0312 (3)
H4A0.93970.10370.28250.037*
H4B0.89210.05400.36750.037*
C50.82268 (8)0.16811 (14)0.23802 (11)0.0240 (3)
C60.77439 (8)0.26933 (14)0.26782 (11)0.0221 (3)
C70.69728 (8)0.31300 (14)0.18198 (11)0.0218 (3)
H7A0.67040.23330.14090.026*
C80.64109 (8)0.37442 (14)0.24284 (11)0.0232 (3)
C90.66851 (8)0.42081 (14)0.34996 (12)0.0242 (3)
C100.71174 (8)0.40744 (14)0.09521 (11)0.0223 (3)
C110.75097 (8)0.53337 (14)0.11377 (12)0.0233 (3)
C120.78991 (8)0.60792 (15)0.20974 (12)0.0269 (3)
H12A0.79700.57360.28350.032*
C130.81773 (9)0.73194 (16)0.19525 (13)0.0308 (3)
H13A0.84380.78270.25990.037*
C140.80824 (9)0.78432 (16)0.08691 (14)0.0317 (3)
H14A0.82770.87000.07960.038*
C150.77111 (9)0.71327 (16)−0.00918 (13)0.0297 (3)
H15A0.76470.7485−0.08250.036*
C160.74337 (8)0.58779 (15)0.00536 (12)0.0249 (3)
C170.68333 (8)0.39281 (14)−0.01990 (11)0.0246 (3)
H17A0.65400.3189−0.05680.029*
C180.55550 (8)0.38803 (15)0.18007 (12)0.0266 (3)
C190.45226 (9)0.32978 (17)0.01690 (13)0.0317 (3)
H19A0.43820.42320.00000.038*
H19B0.41710.29370.05980.038*
C200.44107 (10)0.2548 (2)−0.09068 (15)0.0436 (4)
H20A0.38500.2606−0.13640.065*
H20B0.45530.1626−0.07310.065*
H20C0.47550.2920−0.13300.065*
C210.62218 (9)0.49093 (17)0.41785 (13)0.0313 (3)
H21A0.58440.55220.36880.047*
H21B0.65920.53960.47960.047*
H21C0.59270.42670.44940.047*
C221.01088 (10)0.1881 (2)0.49980 (15)0.0404 (4)
H22A1.05110.15400.46590.061*
H22B0.99310.11740.54080.061*
H22C1.03420.25920.55250.061*
C230.96694 (10)0.35270 (19)0.34418 (15)0.0390 (4)
H23A1.00710.31970.30950.058*
H23B0.99040.42270.39800.058*
H23C0.92110.38740.28520.058*
C240.67642 (9)0.52313 (17)−0.19626 (12)0.0307 (3)
H24A0.65080.4438−0.23540.046*
H24B0.72260.5459−0.22250.046*
H24C0.63800.5958−0.21260.046*
H1N0.7596 (11)0.414 (2)0.4823 (17)0.033 (5)*
U11U22U33U12U13U23
O10.0361 (5)0.0295 (6)0.0207 (5)0.0038 (4)0.0064 (4)−0.0004 (4)
O20.0284 (6)0.0622 (9)0.0387 (6)0.0099 (6)0.0033 (5)−0.0156 (6)
O30.0226 (5)0.0304 (5)0.0266 (5)0.0016 (4)−0.0001 (4)−0.0026 (4)
N10.0275 (6)0.0286 (6)0.0166 (5)0.0006 (5)0.0029 (4)−0.0013 (5)
N20.0297 (6)0.0276 (6)0.0183 (5)0.0048 (5)0.0058 (4)0.0028 (5)
C10.0251 (6)0.0241 (7)0.0198 (6)−0.0004 (5)0.0040 (5)0.0022 (5)
C20.0279 (7)0.0352 (8)0.0196 (6)0.0020 (6)0.0007 (5)0.0001 (6)
C30.0255 (7)0.0353 (8)0.0253 (7)0.0036 (6)0.0007 (6)0.0006 (6)
C40.0301 (7)0.0331 (8)0.0273 (7)0.0089 (6)0.0034 (6)0.0000 (6)
C50.0277 (7)0.0246 (7)0.0193 (6)0.0008 (5)0.0060 (5)0.0028 (5)
C60.0231 (6)0.0229 (6)0.0187 (6)0.0008 (5)0.0033 (5)0.0023 (5)
C70.0238 (6)0.0218 (6)0.0174 (6)−0.0001 (5)0.0020 (5)0.0005 (5)
C80.0246 (7)0.0232 (7)0.0209 (6)0.0010 (5)0.0050 (5)0.0025 (5)
C90.0261 (7)0.0233 (7)0.0230 (6)−0.0003 (5)0.0064 (5)0.0015 (5)
C100.0234 (6)0.0226 (7)0.0192 (6)0.0032 (5)0.0036 (5)0.0003 (5)
C110.0234 (6)0.0236 (7)0.0226 (6)0.0037 (5)0.0063 (5)0.0026 (5)
C120.0271 (7)0.0280 (7)0.0242 (6)0.0011 (6)0.0051 (5)0.0000 (6)
C130.0302 (7)0.0283 (8)0.0320 (8)−0.0017 (6)0.0062 (6)−0.0036 (6)
C140.0301 (7)0.0243 (7)0.0411 (9)−0.0003 (6)0.0113 (6)0.0050 (6)
C150.0302 (7)0.0300 (8)0.0303 (7)0.0052 (6)0.0113 (6)0.0084 (6)
C160.0237 (6)0.0272 (7)0.0239 (7)0.0053 (5)0.0070 (5)0.0026 (6)
C170.0273 (7)0.0239 (7)0.0209 (6)0.0036 (5)0.0045 (5)0.0001 (5)
C180.0255 (7)0.0286 (7)0.0244 (6)−0.0002 (6)0.0052 (5)0.0013 (6)
C190.0220 (7)0.0335 (8)0.0334 (8)0.0026 (6)−0.0019 (6)−0.0030 (6)
C200.0343 (8)0.0480 (10)0.0385 (9)0.0068 (8)−0.0056 (7)−0.0127 (8)
C210.0309 (7)0.0358 (8)0.0267 (7)0.0018 (6)0.0075 (6)−0.0048 (6)
C220.0294 (8)0.0494 (10)0.0349 (8)0.0077 (7)−0.0025 (6)0.0011 (8)
C230.0295 (7)0.0459 (10)0.0399 (9)−0.0019 (7)0.0074 (6)0.0033 (8)
C240.0369 (8)0.0364 (8)0.0186 (6)0.0082 (6)0.0078 (6)0.0047 (6)
O1—C51.2317 (18)C10—C111.441 (2)
O2—C181.2115 (19)C11—C121.406 (2)
O3—C181.3475 (18)C11—C161.4191 (19)
O3—C191.4578 (16)C12—C131.384 (2)
N1—C11.3648 (19)C12—H12A0.9500
N1—C91.3910 (18)C13—C141.405 (2)
N1—H1N0.86 (2)C13—H13A0.9500
N2—C171.3716 (19)C14—C151.381 (2)
N2—C161.3724 (19)C14—H14A0.9500
N2—C241.4594 (17)C15—C161.397 (2)
C1—C61.3606 (19)C15—H15A0.9500
C1—C21.5002 (18)C17—H17A0.9500
C2—C31.533 (2)C19—C201.495 (2)
C2—H2A0.9900C19—H19A0.9900
C2—H2B0.9900C19—H19B0.9900
C3—C41.531 (2)C20—H20A0.9800
C3—C231.531 (2)C20—H20B0.9800
C3—C221.532 (2)C20—H20C0.9800
C4—C51.5207 (19)C21—H21A0.9800
C4—H4A0.9900C21—H21B0.9800
C4—H4B0.9900C21—H21C0.9800
C5—C61.446 (2)C22—H22A0.9800
C6—C71.5197 (17)C22—H22B0.9800
C7—C101.5146 (19)C22—H22C0.9800
C7—C81.5315 (19)C23—H23A0.9800
C7—H7A1.0000C23—H23B0.9800
C8—C91.355 (2)C23—H23C0.9800
C8—C181.4781 (19)C24—H24A0.9800
C9—C211.503 (2)C24—H24B0.9800
C10—C171.3713 (18)C24—H24C0.9800
C18—O3—C19114.36 (11)C12—C13—C14121.39 (14)
C1—N1—C9122.27 (12)C12—C13—H13A119.3
C1—N1—H1N116.4 (13)C14—C13—H13A119.3
C9—N1—H1N115.4 (13)C15—C14—C13121.05 (14)
C17—N2—C16108.41 (12)C15—C14—H14A119.5
C17—N2—C24126.04 (13)C13—C14—H14A119.5
C16—N2—C24125.07 (13)C14—C15—C16117.61 (14)
C6—C1—N1120.71 (12)C14—C15—H15A121.2
C6—C1—C2123.79 (13)C16—C15—H15A121.2
N1—C1—C2115.48 (12)N2—C16—C15129.41 (13)
C1—C2—C3112.70 (12)N2—C16—C11108.03 (13)
C1—C2—H2A109.1C15—C16—C11122.51 (14)
C3—C2—H2A109.1C10—C17—N2110.91 (13)
C1—C2—H2B109.1C10—C17—H17A124.5
C3—C2—H2B109.1N2—C17—H17A124.5
H2A—C2—H2B107.8O2—C18—O3121.90 (13)
C4—C3—C23110.43 (13)O2—C18—C8126.06 (14)
C4—C3—C22110.36 (14)O3—C18—C8112.03 (12)
C23—C3—C22109.28 (14)O3—C19—C20108.07 (12)
C4—C3—C2106.87 (12)O3—C19—H19A110.1
C23—C3—C2111.12 (14)C20—C19—H19A110.1
C22—C3—C2108.75 (13)O3—C19—H19B110.1
C5—C4—C3114.23 (13)C20—C19—H19B110.1
C5—C4—H4A108.7H19A—C19—H19B108.4
C3—C4—H4A108.7C19—C20—H20A109.5
C5—C4—H4B108.7C19—C20—H20B109.5
C3—C4—H4B108.7H20A—C20—H20B109.5
H4A—C4—H4B107.6C19—C20—H20C109.5
O1—C5—C6122.29 (13)H20A—C20—H20C109.5
O1—C5—C4119.05 (13)H20B—C20—H20C109.5
C6—C5—C4118.54 (12)C9—C21—H21A109.5
C1—C6—C5118.99 (12)C9—C21—H21B109.5
C1—C6—C7121.21 (13)H21A—C21—H21B109.5
C5—C6—C7119.73 (12)C9—C21—H21C109.5
C10—C7—C6112.57 (11)H21A—C21—H21C109.5
C10—C7—C8110.43 (11)H21B—C21—H21C109.5
C6—C7—C8109.99 (11)C3—C22—H22A109.5
C10—C7—H7A107.9C3—C22—H22B109.5
C6—C7—H7A107.9H22A—C22—H22B109.5
C8—C7—H7A107.9C3—C22—H22C109.5
C9—C8—C18119.84 (13)H22A—C22—H22C109.5
C9—C8—C7121.71 (12)H22B—C22—H22C109.5
C18—C8—C7118.39 (12)C3—C23—H23A109.5
C8—C9—N1119.58 (13)C3—C23—H23B109.5
C8—C9—C21127.93 (13)H23A—C23—H23B109.5
N1—C9—C21112.48 (12)C3—C23—H23C109.5
C17—C10—C11105.93 (12)H23A—C23—H23C109.5
C17—C10—C7125.43 (13)H23B—C23—H23C109.5
C11—C10—C7128.46 (12)N2—C24—H24A109.5
C12—C11—C16118.31 (13)N2—C24—H24B109.5
C12—C11—C10134.96 (13)H24A—C24—H24B109.5
C16—C11—C10106.70 (12)N2—C24—H24C109.5
C13—C12—C11119.12 (14)H24A—C24—H24C109.5
C13—C12—H12A120.4H24B—C24—H24C109.5
C11—C12—H12A120.4
C9—N1—C1—C612.1 (2)C6—C7—C10—C17126.79 (14)
C9—N1—C1—C2−166.63 (13)C8—C7—C10—C17−109.86 (15)
C6—C1—C2—C323.2 (2)C6—C7—C10—C11−58.89 (18)
N1—C1—C2—C3−158.12 (13)C8—C7—C10—C1164.47 (17)
C1—C2—C3—C4−51.15 (17)C17—C10—C11—C12177.98 (16)
C1—C2—C3—C2369.39 (17)C7—C10—C11—C122.8 (3)
C1—C2—C3—C22−170.29 (14)C17—C10—C11—C16−0.02 (15)
C23—C3—C4—C5−67.55 (17)C7—C10—C11—C16−175.22 (13)
C22—C3—C4—C5171.52 (13)C16—C11—C12—C131.4 (2)
C2—C3—C4—C553.44 (17)C10—C11—C12—C13−176.46 (15)
C3—C4—C5—O1157.14 (14)C11—C12—C13—C14−0.3 (2)
C3—C4—C5—C6−26.6 (2)C12—C13—C14—C15−0.4 (2)
N1—C1—C6—C5−171.47 (13)C13—C14—C15—C160.1 (2)
C2—C1—C6—C57.2 (2)C17—N2—C16—C15−175.84 (14)
N1—C1—C6—C75.7 (2)C24—N2—C16—C15−3.4 (2)
C2—C1—C6—C7−175.67 (13)C17—N2—C16—C111.48 (15)
O1—C5—C6—C1170.63 (13)C24—N2—C16—C11173.94 (13)
C4—C5—C6—C1−5.5 (2)C14—C15—C16—N2178.00 (14)
O1—C5—C6—C7−6.6 (2)C14—C15—C16—C111.0 (2)
C4—C5—C6—C7177.32 (13)C12—C11—C16—N2−179.29 (12)
C1—C6—C7—C10103.36 (15)C10—C11—C16—N2−0.90 (15)
C5—C6—C7—C10−79.50 (16)C12—C11—C16—C15−1.7 (2)
C1—C6—C7—C8−20.24 (19)C10—C11—C16—C15176.65 (13)
C5—C6—C7—C8156.90 (12)C11—C10—C17—N20.95 (16)
C10—C7—C8—C9−104.62 (15)C7—C10—C17—N2176.33 (12)
C6—C7—C8—C920.22 (19)C16—N2—C17—C10−1.55 (16)
C10—C7—C8—C1872.63 (16)C24—N2—C17—C10−173.91 (13)
C6—C7—C8—C18−162.53 (12)C19—O3—C18—O20.3 (2)
C18—C8—C9—N1177.22 (13)C19—O3—C18—C8−178.99 (12)
C7—C8—C9—N1−5.6 (2)C9—C8—C18—O211.2 (2)
C18—C8—C9—C21−1.5 (2)C7—C8—C18—O2−166.16 (16)
C7—C8—C9—C21175.75 (14)C9—C8—C18—O3−169.60 (13)
C1—N1—C9—C8−12.1 (2)C7—C8—C18—O313.10 (18)
C1—N1—C9—C21166.76 (13)C18—O3—C19—C20176.22 (14)
D—H···AD—HH···AD···AD—H···A
C21—H21A···O20.982.282.8073 (19)113
N1—H1N···O1i0.86 (2)1.98 (2)2.8161 (15)163.9 (19)
C24—H24C···O2ii0.982.603.1693 (19)118
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
C21—H21A⋯O20.982.282.8073 (19)113
N1—H1N⋯O1i 0.86 (2)1.98 (2)2.8161 (15)163.9 (19)
C24—H24C⋯O2ii 0.982.603.1693 (19)118

Symmetry codes: (i) ; (ii) .

  10 in total

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Authors:  Annette C Dolphin
Journal:  Br J Pharmacol       Date:  2006-01       Impact factor: 8.739

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Combinatorial synthesis and screening of a chemical library of 1,4-dihydropyridine calcium channel blockers.

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Journal:  Bioorg Med Chem       Date:  1998-07       Impact factor: 3.641

4.  Pharmacology of agents that affect calcium. Agonists and antagonists.

Authors:  D J Triggle; V C Swamy
Journal:  Chest       Date:  1980-07       Impact factor: 9.410

Review 5.  Fused 1,4-dihydropyridines as potential calcium modulatory compounds.

Authors:  Cihat Safak; Rahime Simsek
Journal:  Mini Rev Med Chem       Date:  2006-07       Impact factor: 3.862

Review 6.  The 1,4-dihydropyridine nucleus: a pharmacophoric template part 1. Actions at ion channels.

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Journal:  Mini Rev Med Chem       Date:  2003-05       Impact factor: 3.862

7.  Receptor pharmacology of calcium entry blocking agents.

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Journal:  Am J Cardiol       Date:  1987-01-23       Impact factor: 2.778

8.  3,3,6,6-Tetra-methyl-9-(1-methyl-1H-indol-2-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

Authors:  Sema Oztürk Yildirim; Ray J Butcher; Ahmed El-Khouly; Cihat Safak; Rahime Simsek
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-17

9.  9-(5-Bromo-1H-indol-3-yl)-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione dimethyl sulfoxide monosolvate.

Authors:  Ahmed El-Khouly; Sema Oztürk Yildirim; Ray J Butcher; Rahime Simsek; Cihat Safak
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1.  Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexa-hydro-quinoline derivative: tert-butyl 4-([1,1'-biphen-yl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

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