Literature DB >> 22589945

2-[(1H-Imidazol-1-yl)meth-yl]-1-[4-(trifluoro-meth-yl)phen-yl]-1H-indole.

Rui Wang1, Hong-Fan Shi, Lin Du, Jing-Feng Zhao, Jian-Ping Liu.   

Abstract

In the title compound, C(19)H(14)F(3)N(3), the dihedral angles between the mean planes of the indole ring and the 4-CF(3)-phenyl and imidazole rings are 54.95 (4) and 61.36 (7)°, respectively.

Entities:  

Year:  2012        PMID： 22589945      PMCID： PMC3344036          DOI： 10.1107/S1600536812010471

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


Related literature

For background to indole derivatives and their biological activity, see: Muftuoglua & Mustatab (2010 ▶); Jiao et al. (2010 ▶). For related structures, see: Borgne et al. (1999 ▶); Lézé et al. (2006 ▶); Marchand et al. (2003 ▶).

Experimental

Crystal data

C19H14F3N3 M = 341.33 Orthorhombic, a = 10.3732 (17) Å b = 7.9960 (13) Å c = 37.665 (6) Å V = 3124.0 (9) Å3 Z = 8 Mo Kα radiation μ = 0.11 mm−1 T = 100 K 0.53 × 0.26 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.943, T max = 0.994 30000 measured reflections 4505 independent reflections 3217 reflections with I > 2σ(I) R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.079 wR(F 2) = 0.214 S = 0.99 4505 reflections 226 parameters H-atom parameters constrained Δρmax = 0.51 e Å−3 Δρmin = −0.38 e Å−3 Data collection: APEX2 (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010471/jj2125sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010471/jj2125Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812010471/jj2125Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H14F3N3F(000) = 1408
Mr = 341.33Dx = 1.451 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5075 reflections
a = 10.3732 (17) Åθ = 2.2–30.1°
b = 7.9960 (13) ŵ = 0.11 mm−1
c = 37.665 (6) ÅT = 100 K
V = 3124.0 (9) Å3Laminiplantation, colourless
Z = 80.53 × 0.26 × 0.05 mm
Bruker APEXII CCD diffractometer4505 independent reflections
Radiation source: fine-focus sealed tube3217 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.093
Detector resolution: 0.71 pixels mm-1θmax = 30.2°, θmin = 1.1°
φ and ω scansh = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)k = −11→11
Tmin = 0.943, Tmax = 0.994l = −52→52
30000 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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.214H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0877P)2 + 8.8995P] where P = (Fo2 + 2Fc2)/3
4505 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.51 e Å−3
0 restraintsΔρmin = −0.38 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
F1−0.1652 (2)0.1525 (3)0.97255 (6)0.0444 (6)
F2−0.1194 (2)0.4118 (3)0.97874 (6)0.0422 (6)
F3−0.0238 (2)0.2278 (3)1.01033 (5)0.0430 (6)
N10.3126 (2)0.1845 (3)0.86957 (5)0.0130 (4)
N20.0946 (2)0.1498 (3)0.80082 (6)0.0141 (4)
N3−0.0810 (2)0.2676 (3)0.77776 (7)0.0229 (5)
C10.2961 (3)0.1098 (3)0.83609 (6)0.0133 (5)
C20.4120 (3)0.1060 (3)0.81894 (6)0.0143 (5)
H20.42750.05960.79610.017*
C30.6355 (3)0.2300 (4)0.83646 (7)0.0192 (6)
H30.68020.19960.81540.023*
C40.6967 (3)0.3203 (4)0.86292 (8)0.0228 (6)
H40.78390.35350.85980.027*
C50.6313 (3)0.3638 (4)0.89460 (7)0.0215 (6)
H50.67580.42480.91240.026*
C60.5041 (3)0.3194 (4)0.90018 (7)0.0167 (5)
H60.46040.34840.92150.020*
C70.4424 (2)0.2299 (3)0.87310 (7)0.0147 (5)
C80.5063 (3)0.1844 (3)0.84135 (7)0.0151 (5)
C90.2173 (3)0.2037 (3)0.89657 (7)0.0140 (5)
C100.1007 (2)0.2828 (3)0.88912 (7)0.0144 (5)
H100.08410.32420.86590.017*
C110.0090 (3)0.3010 (4)0.91571 (7)0.0168 (5)
H11−0.07120.35300.91060.020*
C120.0349 (3)0.2429 (3)0.94987 (7)0.0160 (5)
C130.1510 (3)0.1651 (3)0.95761 (7)0.0170 (5)
H130.16790.12570.98090.020*
C140.2428 (3)0.1450 (3)0.93089 (6)0.0164 (5)
H140.32250.09160.93600.020*
C15−0.0667 (3)0.2588 (4)0.97782 (7)0.0205 (6)
C160.1706 (3)0.0383 (3)0.82356 (7)0.0152 (5)
H16A0.1884−0.06610.81030.018*
H16B0.11810.00830.84460.018*
C17−0.0343 (3)0.1775 (4)0.80402 (7)0.0189 (5)
H17−0.08490.13640.82310.023*
C180.0239 (3)0.2973 (4)0.75601 (7)0.0202 (6)
H180.02070.35960.73460.024*
C190.1328 (3)0.2251 (3)0.76948 (7)0.0166 (5)
H190.21690.22640.75950.020*
U11U22U33U12U13U23
F10.0345 (11)0.0602 (15)0.0383 (12)−0.0245 (11)0.0181 (9)−0.0139 (11)
F20.0478 (13)0.0346 (11)0.0444 (12)0.0137 (10)0.0285 (10)0.0034 (10)
F30.0367 (11)0.0788 (17)0.0134 (9)0.0105 (11)0.0078 (8)0.0042 (10)
N10.0148 (10)0.0162 (10)0.0081 (9)0.0008 (8)−0.0002 (8)0.0005 (8)
N20.0169 (11)0.0151 (10)0.0105 (10)−0.0008 (8)−0.0006 (8)−0.0022 (8)
N30.0195 (12)0.0278 (13)0.0215 (12)0.0005 (10)−0.0042 (10)−0.0042 (10)
C10.0195 (12)0.0123 (11)0.0082 (10)0.0026 (9)0.0004 (9)0.0018 (9)
C20.0207 (13)0.0143 (11)0.0079 (10)0.0023 (10)0.0011 (9)−0.0015 (9)
C30.0161 (13)0.0258 (14)0.0157 (12)0.0045 (11)0.0025 (10)0.0014 (11)
C40.0149 (12)0.0335 (16)0.0202 (13)−0.0007 (11)0.0004 (10)−0.0006 (12)
C50.0167 (13)0.0314 (15)0.0165 (13)−0.0001 (11)−0.0042 (10)−0.0047 (11)
C60.0173 (12)0.0213 (13)0.0114 (11)0.0022 (10)0.0001 (9)−0.0021 (10)
C70.0145 (11)0.0171 (12)0.0123 (11)0.0021 (9)−0.0007 (9)0.0008 (9)
C80.0172 (12)0.0177 (12)0.0104 (11)0.0040 (10)−0.0001 (9)−0.0002 (9)
C90.0186 (12)0.0132 (11)0.0102 (11)−0.0002 (9)0.0027 (9)−0.0011 (9)
C100.0177 (12)0.0170 (12)0.0085 (11)−0.0010 (10)−0.0009 (9)0.0014 (9)
C110.0163 (12)0.0216 (13)0.0125 (12)0.0004 (10)−0.0007 (9)−0.0006 (10)
C120.0188 (12)0.0188 (12)0.0104 (11)−0.0032 (10)0.0021 (10)−0.0014 (9)
C130.0236 (13)0.0197 (13)0.0076 (11)−0.0016 (10)−0.0014 (10)0.0015 (9)
C140.0190 (12)0.0196 (13)0.0106 (11)0.0023 (10)−0.0005 (10)0.0009 (10)
C150.0214 (13)0.0254 (15)0.0148 (12)−0.0026 (11)0.0068 (10)−0.0013 (10)
C160.0209 (13)0.0144 (12)0.0103 (11)−0.0026 (10)−0.0023 (10)0.0006 (9)
C170.0148 (12)0.0262 (14)0.0157 (12)−0.0012 (11)0.0008 (10)−0.0039 (11)
C180.0271 (14)0.0198 (13)0.0136 (12)0.0003 (11)−0.0043 (11)−0.0019 (10)
C190.0208 (13)0.0175 (12)0.0115 (11)−0.0012 (10)−0.0006 (10)−0.0003 (10)
F1—C151.344 (4)C5—H50.9500
F2—C151.340 (4)C6—C71.401 (4)
F3—C151.326 (3)C6—H60.9500
N1—C71.400 (3)C7—C81.415 (4)
N1—C11.406 (3)C9—C101.393 (4)
N1—C91.427 (3)C9—C141.400 (3)
N2—C171.360 (3)C10—C111.389 (4)
N2—C191.383 (3)C10—H100.9500
N2—C161.466 (3)C11—C121.394 (4)
N3—C171.316 (4)C11—H110.9500
N3—C181.383 (4)C12—C131.387 (4)
C1—C21.365 (4)C12—C151.495 (4)
C1—C161.498 (4)C13—C141.395 (4)
C2—C81.436 (4)C13—H130.9500
C2—H20.9500C14—H140.9500
C3—C41.385 (4)C16—H16A0.9900
C3—C81.401 (4)C16—H16B0.9900
C3—H30.9500C17—H170.9500
C4—C51.416 (4)C18—C191.366 (4)
C4—H40.9500C18—H180.9500
C5—C61.382 (4)C19—H190.9500
C7—N1—C1108.2 (2)C11—C10—H10120.1
C7—N1—C9124.8 (2)C9—C10—H10120.1
C1—N1—C9126.9 (2)C10—C11—C12119.9 (3)
C17—N2—C19106.6 (2)C10—C11—H11120.0
C17—N2—C16125.1 (2)C12—C11—H11120.0
C19—N2—C16127.5 (2)C13—C12—C11120.7 (2)
C17—N3—C18104.4 (2)C13—C12—C15120.2 (2)
C2—C1—N1109.0 (2)C11—C12—C15119.0 (3)
C2—C1—C16127.4 (2)C12—C13—C14119.5 (2)
N1—C1—C16123.4 (2)C12—C13—H13120.2
C1—C2—C8108.2 (2)C14—C13—H13120.2
C1—C2—H2125.9C13—C14—C9119.9 (2)
C8—C2—H2125.9C13—C14—H14120.1
C4—C3—C8118.7 (3)C9—C14—H14120.1
C4—C3—H3120.7F3—C15—F2106.5 (2)
C8—C3—H3120.7F3—C15—F1105.9 (2)
C3—C4—C5121.0 (3)F2—C15—F1105.7 (3)
C3—C4—H4119.5F3—C15—C12113.4 (2)
C5—C4—H4119.5F2—C15—C12112.5 (2)
C6—C5—C4121.5 (3)F1—C15—C12112.2 (2)
C6—C5—H5119.3N2—C16—C1114.8 (2)
C4—C5—H5119.3N2—C16—H16A108.6
C5—C6—C7117.2 (2)C1—C16—H16A108.6
C5—C6—H6121.4N2—C16—H16B108.6
C7—C6—H6121.4C1—C16—H16B108.6
N1—C7—C6129.9 (2)H16A—C16—H16B107.6
N1—C7—C8107.7 (2)N3—C17—N2112.6 (3)
C6—C7—C8122.1 (2)N3—C17—H17123.7
C3—C8—C7119.5 (2)N2—C17—H17123.7
C3—C8—C2133.5 (2)C19—C18—N3111.0 (2)
C7—C8—C2106.8 (2)C19—C18—H18124.5
C10—C9—C14120.2 (2)N3—C18—H18124.5
C10—C9—N1120.5 (2)C18—C19—N2105.3 (2)
C14—C9—N1119.4 (2)C18—C19—H19127.4
C11—C10—C9119.8 (2)N2—C19—H19127.4
C7—N1—C1—C20.6 (3)C14—C9—C10—C11−1.0 (4)
C9—N1—C1—C2−176.1 (2)N1—C9—C10—C11−179.8 (2)
C7—N1—C1—C16177.2 (2)C9—C10—C11—C121.2 (4)
C9—N1—C1—C160.4 (4)C10—C11—C12—C13−0.8 (4)
N1—C1—C2—C8−1.6 (3)C10—C11—C12—C15−178.1 (3)
C16—C1—C2—C8−178.0 (2)C11—C12—C13—C140.1 (4)
C8—C3—C4—C51.0 (5)C15—C12—C13—C14177.4 (3)
C3—C4—C5—C6−0.6 (5)C12—C13—C14—C90.1 (4)
C4—C5—C6—C7−0.2 (4)C10—C9—C14—C130.4 (4)
C1—N1—C7—C6174.3 (3)N1—C9—C14—C13179.1 (2)
C9—N1—C7—C6−8.9 (4)C13—C12—C15—F314.2 (4)
C1—N1—C7—C80.6 (3)C11—C12—C15—F3−168.5 (3)
C9—N1—C7—C8177.4 (2)C13—C12—C15—F2135.1 (3)
C5—C6—C7—N1−172.3 (3)C11—C12—C15—F2−47.5 (4)
C5—C6—C7—C80.6 (4)C13—C12—C15—F1−105.8 (3)
C4—C3—C8—C7−0.6 (4)C11—C12—C15—F171.6 (4)
C4—C3—C8—C2173.6 (3)C17—N2—C16—C1−134.7 (3)
N1—C7—C8—C3174.1 (2)C19—N2—C16—C156.1 (3)
C6—C7—C8—C3−0.2 (4)C2—C1—C16—N2−86.5 (3)
N1—C7—C8—C2−1.5 (3)N1—C1—C16—N297.6 (3)
C6—C7—C8—C2−175.8 (2)C18—N3—C17—N21.0 (3)
C1—C2—C8—C3−172.8 (3)C19—N2—C17—N3−1.5 (3)
C1—C2—C8—C71.9 (3)C16—N2—C17—N3−172.5 (2)
C7—N1—C9—C10129.0 (3)C17—N3—C18—C19−0.2 (3)
C1—N1—C9—C10−54.7 (4)N3—C18—C19—N2−0.7 (3)
C7—N1—C9—C14−49.7 (4)C17—N2—C19—C181.2 (3)
C1—N1—C9—C14126.5 (3)C16—N2—C19—C18172.0 (2)
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3.  New selective nonsteroidal aromatase inhibitors: synthesis and inhibitory activity of 2,3 or 5-(alpha-azolylbenzyl)-1H-indoles.

Authors:  M Le Borgne; P Marchand; B Delevoye-Seiller; J M Robert; G Le Baut; R W Hartmann; M Palzer
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Review 4.  Recent advancement in nonsteroidal aromatase inhibitors for treatment of estrogen-dependent breast cancer.

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5.  Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: potent and selective aromatase inhibitors.

Authors:  Marie-Pierre Lézé; Marc Le Borgne; Patricia Pinson; Anja Palusczak; Muriel Duflos; Guillaume Le Baut; Rolf W Hartmann
Journal:  Bioorg Med Chem Lett       Date:  2005-12-27       Impact factor: 2.823

6.  Preparation and pharmacological profile of 7-(alpha-azolylbenzyl)-1H-indoles and indolines as new aromatase inhibitors.

Authors:  Pascal Marchand; Marc Le Borgne; Martina Palzer; Guillaume Le Baut; Rolf W Hartmann
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  6 in total

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