Literature DB >> 22590001

2-(Piperidin-1-yl)-6-(1H-pyrrol-1-yl)pyridine-3,5-dicarbonitrile.

Peter N Horton, Shaaban K Mohamed, Ahmed M Soliman, Eman M M Abdel-Raheem, Mehmet Akkurt.   

Abstract

The piperidine ring of the title compound, C(16)H(15)N(5), adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.035 (3) Å. The pyrrole and pyridine rings are almost coplanar, forming a dihedral angle of 3.48 (14)°. In the crystal, no classical hydrogen bonds were found. In the crystal, the molecules are linked by aromatic π-π stacking [centroid-centroid separations = 3.4984 (16) and 3.9641 (15) Å between pyrrole and pyridine rings and between pyridine rings, respectively].

Entities:  

Year:  2012        PMID： 22590001      PMCID： PMC3343920          DOI： 10.1107/S1600536812008586

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


Related literature

For the biological activity of cyano-amino pyridines, see: Al-Haiza et al. (2003 ▶); Bhalerao & Krishnaiah (1995 ▶); Doe et al. (1990 ▶); Murata et al. (2003 ▶); Shankaraiah et al. (2010 ▶); Shishoo et al. (1983 ▶); Soliman et al. (2012 ▶); Temple et al. (1992 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H15N5 M = 277.33 Monoclinic, a = 11.9372 (16) Å b = 6.6919 (8) Å c = 17.158 (2) Å β = 92.280 (7)° V = 1369.5 (3) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 100 K 0.32 × 0.04 × 0.02 mm

Data collection

Rigaku Saturn724+ diffractometer Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.973, T max = 0.998 7877 measured reflections 3098 independent reflections 1503 reflections with I > 2σ(I) R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.073 wR(F 2) = 0.140 S = 0.96 3098 reflections 190 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.24 e Å−3 Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SIR2004 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008586/xu5473sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008586/xu5473Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812008586/xu5473Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H15N5F(000) = 584
Mr = 277.33Dx = 1.345 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4756 reflections
a = 11.9372 (16) Åθ = 3.3–27.5°
b = 6.6919 (8) ŵ = 0.09 mm−1
c = 17.158 (2) ÅT = 100 K
β = 92.280 (7)°Lath, colourless
V = 1369.5 (3) Å30.32 × 0.04 × 0.02 mm
Z = 4
Rigaku Saturn724+ diffractometer3098 independent reflections
Radiation source: Rotating Anode1503 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.095
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 3.3°
profile data from ω–scansh = −15→15
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)k = −7→8
Tmin = 0.973, Tmax = 0.998l = −21→22
7877 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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0431P)2] where P = (Fo2 + 2Fc2)/3
3098 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Experimental. CrystalClear-SM Expert
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
N10.57393 (18)0.2530 (3)0.06283 (13)0.0173 (7)
N20.38710 (18)0.2792 (3)0.03066 (13)0.0168 (7)
N30.75463 (17)0.2158 (3)0.11176 (13)0.0192 (7)
N40.3876 (2)0.2027 (4)−0.19418 (14)0.0312 (9)
N50.9243 (2)0.2228 (3)−0.06919 (14)0.0262 (8)
C10.4966 (2)0.2520 (4)0.00532 (16)0.0169 (9)
C20.5227 (2)0.2225 (4)−0.07288 (15)0.0150 (8)
C30.6365 (2)0.2034 (4)−0.08826 (15)0.0180 (9)
C40.7185 (2)0.2039 (4)−0.02904 (15)0.0167 (9)
C50.6829 (2)0.2212 (4)0.04902 (15)0.0153 (8)
C60.4457 (2)0.2118 (4)−0.13900 (16)0.0209 (9)
C70.8327 (2)0.2111 (4)−0.05098 (15)0.0174 (9)
C80.2865 (2)0.2905 (4)−0.01382 (17)0.0207 (9)
C90.2014 (2)0.3079 (4)0.03534 (16)0.0206 (9)
C100.2483 (2)0.3078 (4)0.11287 (16)0.0199 (9)
C110.3609 (2)0.2903 (4)0.10890 (16)0.0191 (9)
C120.7216 (2)0.2875 (4)0.18847 (16)0.0250 (9)
C130.8159 (2)0.4145 (4)0.22429 (17)0.0255 (10)
C140.9264 (2)0.3013 (4)0.22895 (17)0.0263 (10)
C150.9552 (2)0.2224 (4)0.14853 (17)0.0233 (9)
C160.8582 (2)0.0981 (4)0.11522 (16)0.0212 (9)
H30.657500.19000−0.139600.0220*
H80.279400.28670−0.068000.0250*
H90.125700.318000.021000.0250*
H100.208600.318000.158300.0240*
H110.412000.286300.151200.0230*
H12A0.707000.174800.222200.0300*
H12B0.653500.366300.182700.0300*
H13A0.796500.455400.276300.0310*
H13B0.824400.534100.193100.0310*
H14A0.921000.190400.265000.0320*
H14B0.985700.389400.248500.0320*
H15A0.969400.333400.113900.0280*
H15B1.022400.141100.152900.0280*
H16A0.874900.053000.063200.0250*
H16B0.84820−0.018800.147600.0250*
U11U22U33U12U13U23
N10.0151 (12)0.0199 (13)0.0168 (13)−0.0004 (10)−0.0007 (10)0.0011 (10)
N20.0133 (11)0.0187 (12)0.0183 (13)0.0017 (10)0.0011 (9)−0.0014 (10)
N30.0146 (12)0.0250 (13)0.0179 (13)0.0045 (10)0.0004 (10)−0.0054 (11)
N40.0255 (14)0.0450 (17)0.0230 (15)0.0032 (13)−0.0010 (12)−0.0044 (13)
N50.0203 (14)0.0315 (15)0.0267 (15)0.0043 (12)0.0014 (11)−0.0003 (12)
C10.0169 (14)0.0124 (15)0.0213 (16)−0.0017 (11)0.0012 (12)0.0013 (11)
C20.0158 (14)0.0143 (15)0.0146 (14)−0.0008 (12)−0.0030 (11)0.0021 (11)
C30.0235 (15)0.0159 (15)0.0149 (15)−0.0011 (13)0.0049 (12)−0.0010 (12)
C40.0178 (15)0.0158 (15)0.0166 (15)−0.0001 (13)0.0006 (12)0.0003 (12)
C50.0144 (14)0.0155 (15)0.0161 (15)−0.0038 (12)0.0009 (11)−0.0011 (11)
C60.0185 (15)0.0262 (16)0.0183 (15)0.0012 (13)0.0038 (13)0.0002 (13)
C70.0212 (15)0.0182 (15)0.0126 (15)0.0034 (13)−0.0012 (12)0.0007 (12)
C80.0187 (15)0.0206 (16)0.0227 (16)0.0008 (13)−0.0016 (12)0.0012 (13)
C90.0162 (15)0.0227 (16)0.0229 (17)−0.0004 (13)0.0025 (12)−0.0010 (13)
C100.0185 (15)0.0186 (16)0.0231 (16)−0.0027 (12)0.0065 (12)0.0003 (13)
C110.0198 (15)0.0214 (15)0.0160 (15)−0.0013 (13)0.0003 (12)−0.0010 (13)
C120.0184 (15)0.0321 (17)0.0243 (17)−0.0003 (14)0.0000 (12)−0.0095 (14)
C130.0227 (17)0.0302 (18)0.0233 (17)0.0015 (14)−0.0017 (13)−0.0052 (14)
C140.0215 (16)0.0304 (18)0.0268 (17)−0.0030 (14)−0.0022 (13)−0.0068 (15)
C150.0157 (15)0.0266 (17)0.0278 (17)−0.0013 (13)0.0019 (12)−0.0004 (14)
C160.0186 (15)0.0251 (16)0.0199 (17)0.0039 (13)0.0016 (13)−0.0002 (12)
N1—C11.324 (3)C12—C131.521 (4)
N1—C51.348 (3)C13—C141.520 (3)
N2—C11.406 (3)C14—C151.529 (4)
N2—C81.399 (3)C15—C161.519 (4)
N2—C111.392 (4)C3—H30.9300
N3—C51.349 (3)C8—H80.9300
N3—C121.470 (3)C9—H90.9300
N3—C161.465 (3)C10—H100.9300
N4—C61.153 (4)C11—H110.9300
N5—C71.152 (3)C12—H12A0.9700
C1—C21.403 (4)C12—H12B0.9700
C2—C31.400 (3)C13—H13A0.9700
C2—C61.433 (4)C13—H13B0.9700
C3—C41.383 (4)C14—H14A0.9700
C4—C51.426 (4)C14—H14B0.9700
C4—C71.429 (3)C15—H15A0.9700
C8—C91.351 (4)C15—H15B0.9700
C9—C101.423 (4)C16—H16A0.9700
C10—C111.354 (3)C16—H16B0.9700
C1—N1—C5121.1 (2)N2—C8—H8126.00
C1—N2—C8128.8 (2)C9—C8—H8126.00
C1—N2—C11123.5 (2)C8—C9—H9126.00
C8—N2—C11107.6 (2)C10—C9—H9126.00
C5—N3—C12121.4 (2)C9—C10—H10126.00
C5—N3—C16123.7 (2)C11—C10—H10126.00
C12—N3—C16113.3 (2)N2—C11—H11126.00
N1—C1—N2113.5 (2)C10—C11—H11126.00
N1—C1—C2122.6 (2)N3—C12—H12A110.00
N2—C1—C2124.0 (2)N3—C12—H12B110.00
C1—C2—C3116.6 (2)C13—C12—H12A110.00
C1—C2—C6127.2 (2)C13—C12—H12B110.00
C3—C2—C6116.3 (2)H12A—C12—H12B108.00
C2—C3—C4121.7 (2)C12—C13—H13A109.00
C3—C4—C5117.5 (2)C12—C13—H13B109.00
C3—C4—C7117.5 (2)C14—C13—H13A109.00
C5—C4—C7124.6 (2)C14—C13—H13B109.00
N1—C5—N3116.8 (2)H13A—C13—H13B108.00
N1—C5—C4120.2 (2)C13—C14—H14A110.00
N3—C5—C4123.0 (2)C13—C14—H14B110.00
N4—C6—C2177.1 (3)C15—C14—H14A110.00
N5—C7—C4178.0 (3)C15—C14—H14B110.00
N2—C8—C9108.3 (2)H14A—C14—H14B108.00
C8—C9—C10107.8 (2)C14—C15—H15A110.00
C9—C10—C11107.9 (2)C14—C15—H15B110.00
N2—C11—C10108.3 (2)C16—C15—H15A110.00
N3—C12—C13108.9 (2)C16—C15—H15B110.00
C12—C13—C14111.7 (2)H15A—C15—H15B108.00
C13—C14—C15110.5 (2)N3—C16—H16A110.00
C14—C15—C16109.5 (2)N3—C16—H16B110.00
N3—C16—C15110.5 (2)C15—C16—H16A110.00
C2—C3—H3119.00C15—C16—H16B110.00
C4—C3—H3119.00H16A—C16—H16B108.00
C5—N1—C1—N2177.4 (2)N2—C1—C2—C3178.3 (2)
C5—N1—C1—C2−1.4 (4)N2—C1—C2—C6−1.0 (4)
C1—N1—C5—N3−177.0 (2)N1—C1—C2—C6177.7 (3)
C1—N1—C5—C45.8 (4)N1—C1—C2—C3−3.0 (4)
C8—N2—C1—N1178.4 (2)C1—C2—C3—C43.0 (4)
C11—N2—C1—C2174.0 (2)C6—C2—C3—C4−177.6 (3)
C1—N2—C8—C9177.1 (2)C2—C3—C4—C7−171.7 (3)
C1—N2—C11—C10−177.3 (2)C2—C3—C4—C51.1 (4)
C8—N2—C11—C100.0 (3)C3—C4—C5—N1−5.5 (4)
C8—N2—C1—C2−2.8 (4)C7—C4—C5—N3−10.5 (4)
C11—N2—C8—C90.0 (3)C3—C4—C5—N3177.4 (2)
C11—N2—C1—N1−4.8 (3)C7—C4—C5—N1166.6 (2)
C5—N3—C16—C15134.0 (2)N2—C8—C9—C100.0 (3)
C12—N3—C5—N1−14.1 (3)C8—C9—C10—C110.0 (3)
C12—N3—C16—C15−60.3 (3)C9—C10—C11—N20.0 (3)
C16—N3—C5—C4−32.4 (4)N3—C12—C13—C14−55.5 (3)
C5—N3—C12—C13−135.4 (2)C12—C13—C14—C1555.1 (3)
C16—N3—C12—C1358.5 (3)C13—C14—C15—C16−54.7 (3)
C16—N3—C5—N1150.5 (2)C14—C15—C16—N356.7 (3)
C12—N3—C5—C4163.0 (2)
D—H···AD—HH···AD···AD—H···A
C12—H12B···N10.972.362.740 (3)103
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