Literature DB >> 21589027

(E)-N'-(3,3-Dimethyl-2,6-diphenyl-piperidin-4-yl-idene)isonicotinohydrazide.

C Sankar, K Pandiarajan, A Thiruvalluvar, P Gayathri.   

Abstract

In the title mol-ecule, C(25)H(26)N(4)O, the piperidine ring adopts a chair conformation, with the plane through the four coplanar atoms making dihedral angles of 84.76 (6), 82.28 (5) and 81.91 (6)° with the pyridine-ring and the phenyl rings at the 2 and 6 positions, respectively. The pyridine ring makes dihedral angles of 64.13 (8) and 10.75 (8)° with the phenyl rings at the 2 and 6 positions, respectively. The dihedral angle between the two phenyl rings is 53.57 (8)°. The phenyl rings and one of the methyl groups at position 3 have an equatorial orientation. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID： 21589027      PMCID： PMC3009086          DOI： 10.1107/S1600536810040936

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


Related literature

For the high bacteriostatic activity of isonicotinic acid hydrazide (INH) against mycobacterium tuberculosis, see: Hearn & Cynamon (2003 ▶). For Schiff bases of INH as anti­mycobacterial agents, see: Hearn et al. (2009 ▶). For a novel class of anti­mycobacterial agents, see: Jha & Dimmock (2006 ▶). For piperidin-4-ones as anti­bacterial agents, see: Srinivasan et al. (2006 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H26N4O M = 398.50 Triclinic, a = 6.2128 (1) Å b = 12.8346 (3) Å c = 15.0022 (3) Å α = 65.293 (1)° β = 78.823 (1)° γ = 86.948 (1)° V = 1065.62 (4) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 293 K 0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.856, T max = 1.000 25613 measured reflections 5420 independent reflections 3821 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.128 S = 1.01 5420 reflections 281 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.19 e Å−3 Δρmin = −0.17 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-NT (Bruker, 2004 ▶); data reduction: SAINT-NT; 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: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040936/hg2726sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040936/hg2726Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H26N4OZ = 2
Mr = 398.50F(000) = 424
Triclinic, P1Dx = 1.242 Mg m−3
Hall symbol: -P 1Melting point: 490 K
a = 6.2128 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.8346 (3) ÅCell parameters from 9908 reflections
c = 15.0022 (3) Åθ = 1.8–25.0°
α = 65.293 (1)°µ = 0.08 mm−1
β = 78.823 (1)°T = 293 K
γ = 86.948 (1)°Prism, colourless
V = 1065.62 (4) Å30.22 × 0.18 × 0.16 mm
Bruker Kappa APEXII CCD diffractometer5420 independent reflections
Radiation source: fine-focus sealed tube3821 reflections with I > 2σ(I)
graphiteRint = 0.023
ω and φ scanθmax = 28.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −8→8
Tmin = 0.856, Tmax = 1.000k = −17→17
25613 measured reflectionsl = −20→20
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) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0566P)2 + 0.2037P] where P = (Fo2 + 2Fc2)/3
5420 reflections(Δ/σ)max = 0.001
281 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
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 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 > 2σ(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
O141.03274 (18)−0.14364 (9)0.56827 (8)0.0695 (4)
N10.33045 (18)0.26040 (10)0.65579 (8)0.0448 (3)
N40.60062 (18)−0.04110 (9)0.69192 (8)0.0467 (3)
N50.74773 (19)−0.05142 (10)0.61377 (9)0.0514 (4)
N440.7572 (2)−0.44715 (11)0.90685 (10)0.0642 (5)
C20.36826 (19)0.17468 (10)0.75246 (9)0.0414 (3)
C30.3208 (2)0.05259 (11)0.76155 (9)0.0448 (4)
C40.4717 (2)0.04288 (11)0.67242 (9)0.0443 (4)
C50.4554 (2)0.13676 (11)0.57172 (9)0.0496 (4)
C60.4863 (2)0.25405 (11)0.57214 (9)0.0444 (4)
C140.8758 (2)−0.14316 (11)0.63200 (10)0.0488 (4)
C210.2393 (2)0.20405 (10)0.83490 (9)0.0421 (4)
C220.0312 (2)0.24877 (12)0.83080 (10)0.0496 (4)
C23−0.0766 (3)0.28184 (13)0.90385 (11)0.0580 (5)
C240.0198 (3)0.27101 (14)0.98165 (11)0.0636 (5)
C250.2234 (3)0.22530 (15)0.98804 (12)0.0665 (6)
C260.3326 (2)0.19245 (12)0.91516 (10)0.0542 (5)
C310.0813 (2)0.03536 (14)0.75770 (13)0.0622 (5)
C320.3741 (3)−0.03629 (12)0.86027 (10)0.0625 (5)
C410.8240 (2)−0.24660 (11)0.72951 (10)0.0439 (4)
C420.6160 (2)−0.28642 (12)0.78285 (12)0.0558 (5)
C430.5917 (3)−0.38594 (13)0.86975 (12)0.0631 (5)
C450.9553 (3)−0.40873 (13)0.85467 (12)0.0620 (5)
C460.9973 (2)−0.31085 (12)0.76702 (11)0.0538 (4)
C610.4552 (2)0.35141 (11)0.47507 (9)0.0443 (4)
C620.6328 (2)0.39763 (12)0.39928 (10)0.0529 (4)
C630.6084 (3)0.48708 (13)0.30964 (11)0.0613 (5)
C640.4057 (3)0.53062 (13)0.29626 (11)0.0644 (5)
C650.2281 (3)0.48566 (16)0.37049 (13)0.0766 (6)
C660.2510 (3)0.39566 (15)0.45995 (12)0.0689 (5)
H10.345 (2)0.3300 (15)0.6547 (11)0.059 (4)*
H20.524340.180030.753680.0496*
H50.794 (3)0.0072 (16)0.5558 (14)0.075 (5)*
H5A0.567180.127800.520670.0595*
H5B0.312930.131530.556240.0595*
H60.635450.260470.582150.0533*
H22−0.036220.256540.778260.0596*
H23−0.215950.311710.900100.0695*
H24−0.052610.294611.030080.0763*
H250.288080.216381.041640.0798*
H260.471230.161980.919950.0651*
H31A0.06299−0.037150.755270.0934*
H31B−0.012400.036480.816220.0934*
H31C0.043260.095960.699180.0934*
H32A0.52223−0.023340.864040.0938*
H32B0.27505−0.029330.915050.0938*
H32C0.35859−0.111940.863660.0938*
H420.49352−0.246760.760580.0670*
H430.45002−0.411650.904490.0757*
H451.07448−0.450490.878650.0745*
H461.14085−0.288230.733430.0646*
H620.771170.368580.408180.0635*
H630.729830.517460.258630.0736*
H640.389290.591060.236300.0773*
H650.090440.515500.361180.0919*
H660.128310.364800.510130.0826*
U11U22U33U12U13U23
O140.0718 (7)0.0506 (6)0.0626 (7)0.0153 (5)0.0123 (5)−0.0131 (5)
N10.0559 (6)0.0363 (6)0.0362 (6)0.0060 (4)−0.0079 (4)−0.0103 (4)
N40.0519 (6)0.0376 (6)0.0438 (6)0.0072 (4)−0.0037 (5)−0.0133 (5)
N50.0587 (7)0.0419 (6)0.0429 (6)0.0118 (5)−0.0016 (5)−0.0118 (5)
N440.0746 (9)0.0483 (7)0.0572 (8)0.0074 (6)−0.0041 (6)−0.0141 (6)
C20.0412 (6)0.0404 (6)0.0363 (6)0.0043 (5)−0.0081 (5)−0.0099 (5)
C30.0481 (7)0.0372 (6)0.0407 (7)0.0047 (5)−0.0029 (5)−0.0107 (5)
C40.0490 (7)0.0369 (6)0.0419 (7)0.0051 (5)−0.0069 (5)−0.0127 (5)
C50.0582 (8)0.0459 (7)0.0394 (7)0.0141 (6)−0.0088 (6)−0.0142 (6)
C60.0439 (6)0.0435 (7)0.0366 (6)0.0047 (5)−0.0081 (5)−0.0080 (5)
C140.0518 (7)0.0411 (7)0.0492 (7)0.0073 (5)−0.0050 (6)−0.0174 (6)
C210.0491 (7)0.0350 (6)0.0359 (6)0.0016 (5)−0.0086 (5)−0.0085 (5)
C220.0531 (7)0.0509 (8)0.0420 (7)0.0086 (6)−0.0121 (5)−0.0160 (6)
C230.0582 (8)0.0569 (9)0.0543 (8)0.0116 (6)−0.0061 (6)−0.0219 (7)
C240.0834 (11)0.0604 (9)0.0473 (8)0.0067 (8)−0.0058 (7)−0.0261 (7)
C250.0870 (11)0.0714 (10)0.0493 (9)0.0103 (8)−0.0256 (8)−0.0286 (8)
C260.0597 (8)0.0547 (8)0.0498 (8)0.0094 (6)−0.0201 (6)−0.0199 (7)
C310.0533 (8)0.0591 (9)0.0741 (10)−0.0079 (7)0.0000 (7)−0.0316 (8)
C320.0834 (10)0.0430 (8)0.0414 (7)0.0117 (7)0.0001 (7)−0.0047 (6)
C410.0488 (7)0.0374 (6)0.0468 (7)0.0052 (5)−0.0073 (5)−0.0200 (5)
C420.0485 (7)0.0436 (7)0.0700 (10)0.0042 (5)−0.0108 (6)−0.0190 (7)
C430.0585 (9)0.0458 (8)0.0712 (10)−0.0030 (6)0.0018 (7)−0.0164 (7)
C450.0665 (9)0.0547 (9)0.0585 (9)0.0187 (7)−0.0169 (7)−0.0172 (7)
C460.0484 (7)0.0512 (8)0.0569 (8)0.0087 (6)−0.0068 (6)−0.0199 (7)
C610.0513 (7)0.0392 (6)0.0371 (6)0.0028 (5)−0.0091 (5)−0.0107 (5)
C620.0575 (8)0.0434 (7)0.0467 (7)0.0056 (6)−0.0024 (6)−0.0116 (6)
C630.0793 (10)0.0447 (8)0.0439 (8)−0.0021 (7)0.0041 (7)−0.0093 (6)
C640.0909 (12)0.0442 (8)0.0468 (8)0.0019 (7)−0.0235 (8)−0.0034 (6)
C650.0661 (10)0.0710 (11)0.0685 (11)0.0096 (8)−0.0279 (8)0.0001 (9)
C660.0509 (8)0.0719 (10)0.0557 (9)0.0046 (7)−0.0109 (7)0.0007 (8)
O14—C141.2279 (17)C61—C621.3717 (18)
N1—C21.4627 (17)C62—C631.385 (2)
N1—C61.4578 (17)C63—C641.367 (3)
N4—N51.3889 (17)C64—C651.358 (2)
N4—C41.2744 (19)C65—C661.384 (3)
N5—C141.345 (2)C2—H20.9800
N44—C431.325 (2)C5—H5A0.9700
N44—C451.319 (2)C5—H5B0.9700
N1—H10.90 (2)C6—H60.9800
N5—H50.89 (2)C22—H220.9300
C2—C31.554 (2)C23—H230.9300
C2—C211.5123 (18)C24—H240.9300
C3—C41.5242 (18)C25—H250.9300
C3—C321.5303 (19)C26—H260.9300
C3—C311.5314 (18)C31—H31A0.9600
C4—C51.5063 (18)C31—H31B0.9600
C5—C61.530 (2)C31—H31C0.9600
C6—C611.5105 (18)C32—H32A0.9600
C14—C411.499 (2)C32—H32B0.9600
C21—C221.3882 (19)C32—H32C0.9600
C21—C261.3855 (18)C42—H420.9300
C22—C231.380 (2)C43—H430.9300
C23—C241.366 (2)C45—H450.9300
C24—C251.369 (3)C46—H460.9300
C25—C261.379 (2)C62—H620.9300
C41—C421.3781 (19)C63—H630.9300
C41—C461.3814 (19)C64—H640.9300
C42—C431.381 (2)C65—H650.9300
C45—C461.377 (2)C66—H660.9300
C61—C661.382 (2)
O14···N5i2.9648 (17)H2···H32A2.4400
O14···H462.5900H5···C52.65 (2)
O14···H5i2.10 (2)H5···H5A2.0100
O14···H5Ai2.5600H5···O14i2.10 (2)
N4···C422.866 (2)H5···C14i3.037 (19)
N5···O14i2.9648 (17)H5A···N52.4800
N1···H31C2.6200H5A···H52.0100
N1···H222.6200H5A···O14i2.5600
N1···H662.5700H5B···C312.8500
N4···H32A2.6400H5B···H31C2.3400
N4···H32C2.5300H6···H22.3100
N4···H422.4700H6···H622.3900
N5···H5A2.4800H22···N12.6200
N5···H422.8400H22···C313.0200
N44···H43ii2.7400H23···H64iv2.3400
C22···C313.330 (3)H24···C45vi2.8500
C26···C323.350 (2)H26···H22.3600
C31···C223.330 (3)H31A···H32C2.5700
C32···C263.350 (2)H31B···C212.8600
C42···N42.866 (2)H31B···C222.8500
C46···C63i3.596 (2)H31B···H32B2.4300
C46···C62i3.546 (2)H31C···N12.6200
C62···C46i3.546 (2)H31C···C52.8100
C63···C46i3.596 (2)H31C···H5B2.3400
C5···H31C2.8100H32A···N42.6400
C5···H52.65 (2)H32A···H22.4400
C14···H5i3.037 (19)H32B···C212.7400
C21···H32B2.7400H32B···C262.8900
C21···H31B2.8600H32B···H31B2.4300
C22···H63iii3.0600H32C···N42.5300
C22···H31B2.8500H32C···H31A2.5700
C22···H12.790 (14)H32C···C24v3.0800
C23···H64iv3.0400H42···N42.4700
C24···H32Cv3.0800H42···N52.8400
C26···H64iii3.1000H42···H46vii2.4300
C26···H32B2.8900H43···H45vii2.5500
C31···H223.0200H43···N44ii2.7400
C31···H5B2.8500H45···H43viii2.5500
C45···H63i3.0100H46···O142.5900
C45···H24vi2.8500H46···H42viii2.4300
C46···H62i3.0900H46···C62i2.9900
C62···H46i2.9900H62···H62.3900
C63···H1iii2.66 (2)H62···H65viii2.5900
C64···H1iii2.824 (18)H62···C46i3.0900
C66···H12.853 (15)H63···C22iii3.0600
H1···C222.790 (14)H63···C45i3.0100
H1···C662.853 (15)H64···C23iv3.0400
H1···C63iii2.66 (2)H64···C26iii3.1000
H1···C64iii2.824 (18)H64···H23iv2.3400
H2···H62.3100H65···H62vii2.5900
H2···H262.3600H66···N12.5700
C2—N1—C6112.55 (11)C3—C2—H2107.00
N5—N4—C4118.90 (11)C21—C2—H2107.00
N4—N5—C14119.82 (12)C4—C5—H5A110.00
C43—N44—C45116.03 (15)C4—C5—H5B110.00
C2—N1—H1108.0 (9)C6—C5—H5A110.00
C6—N1—H1108.4 (9)C6—C5—H5B110.00
C14—N5—H5114.1 (13)H5A—C5—H5B108.00
N4—N5—H5123.4 (14)N1—C6—H6109.00
N1—C2—C21109.36 (11)C5—C6—H6109.00
C3—C2—C21115.32 (10)C61—C6—H6109.00
N1—C2—C3109.55 (10)C21—C22—H22120.00
C2—C3—C4105.43 (10)C23—C22—H22120.00
C31—C3—C32109.43 (12)C22—C23—H23120.00
C2—C3—C32108.92 (11)C24—C23—H23120.00
C4—C3—C31109.77 (12)C23—C24—H24120.00
C2—C3—C31112.07 (12)C25—C24—H24120.00
C4—C3—C32111.19 (12)C24—C25—H25120.00
N4—C4—C3116.53 (11)C26—C25—H25120.00
N4—C4—C5127.81 (12)C21—C26—H26119.00
C3—C4—C5115.62 (12)C25—C26—H26119.00
C4—C5—C6109.92 (11)C3—C31—H31A109.00
N1—C6—C61110.52 (11)C3—C31—H31B109.00
C5—C6—C61111.96 (11)C3—C31—H31C109.00
N1—C6—C5108.38 (11)H31A—C31—H31B109.00
O14—C14—C41119.65 (13)H31A—C31—H31C109.00
N5—C14—C41120.00 (12)H31B—C31—H31C109.00
O14—C14—N5120.34 (13)C3—C32—H32A109.00
C2—C21—C22122.00 (11)C3—C32—H32B109.00
C2—C21—C26120.12 (12)C3—C32—H32C109.00
C22—C21—C26117.80 (12)H32A—C32—H32B109.00
C21—C22—C23120.70 (13)H32A—C32—H32C109.00
C22—C23—C24120.49 (17)H32B—C32—H32C109.00
C23—C24—C25119.76 (16)C41—C42—H42120.00
C24—C25—C26120.11 (15)C43—C42—H42120.00
C21—C26—C25121.13 (13)N44—C43—H43118.00
C42—C41—C46116.93 (13)C42—C43—H43118.00
C14—C41—C42125.26 (12)N44—C45—H45118.00
C14—C41—C46117.73 (12)C46—C45—H45118.00
C41—C42—C43119.17 (14)C41—C46—H46120.00
N44—C43—C42124.22 (16)C45—C46—H46120.00
N44—C45—C46124.32 (16)C61—C62—H62120.00
C41—C46—C45119.32 (14)C63—C62—H62120.00
C6—C61—C62119.72 (12)C62—C63—H63120.00
C6—C61—C66121.71 (12)C64—C63—H63120.00
C62—C61—C66118.57 (13)C63—C64—H64120.00
C61—C62—C63120.77 (13)C65—C64—H64120.00
C62—C63—C64119.93 (15)C64—C65—H65120.00
C63—C64—C65120.03 (15)C66—C65—H65120.00
C64—C65—C66120.35 (18)C61—C66—H66120.00
C61—C66—C65120.35 (16)C65—C66—H66120.00
N1—C2—H2107.00
C6—N1—C2—C3−66.16 (13)N1—C6—C61—C62147.45 (14)
C6—N1—C2—C21166.56 (11)N1—C6—C61—C66−32.7 (2)
C2—N1—C6—C562.66 (13)C5—C6—C61—C62−91.63 (16)
C2—N1—C6—C61−174.31 (11)C5—C6—C61—C6688.18 (17)
C4—N4—N5—C14−175.94 (13)O14—C14—C41—C42−144.04 (16)
N5—N4—C4—C3−177.47 (12)O14—C14—C41—C4632.6 (2)
N5—N4—C4—C50.2 (2)N5—C14—C41—C4234.5 (2)
N4—N5—C14—O14−166.63 (13)N5—C14—C41—C46−148.87 (14)
N4—N5—C14—C4114.9 (2)C2—C21—C22—C23−175.68 (14)
C45—N44—C43—C42−0.9 (3)C26—C21—C22—C230.9 (2)
C43—N44—C45—C460.6 (3)C2—C21—C26—C25176.00 (15)
N1—C2—C3—C457.28 (12)C22—C21—C26—C25−0.6 (2)
N1—C2—C3—C31−62.09 (14)C21—C22—C23—C24−0.1 (3)
N1—C2—C3—C32176.68 (11)C22—C23—C24—C25−1.1 (3)
C21—C2—C3—C4−178.86 (10)C23—C24—C25—C261.3 (3)
C21—C2—C3—C3161.77 (14)C24—C25—C26—C21−0.4 (3)
C21—C2—C3—C32−59.46 (14)C14—C41—C42—C43177.21 (15)
N1—C2—C21—C2237.55 (17)C46—C41—C42—C430.5 (2)
N1—C2—C21—C26−138.95 (13)C14—C41—C46—C45−177.74 (15)
C3—C2—C21—C22−86.41 (16)C42—C41—C46—C45−0.8 (2)
C3—C2—C21—C2697.09 (15)C41—C42—C43—N440.4 (3)
C2—C3—C4—N4124.14 (13)N44—C45—C46—C410.2 (3)
C2—C3—C4—C5−53.79 (14)C6—C61—C62—C63−179.90 (14)
C31—C3—C4—N4−114.98 (15)C66—C61—C62—C630.3 (2)
C31—C3—C4—C567.09 (16)C6—C61—C66—C65179.38 (17)
C32—C3—C4—N46.26 (18)C62—C61—C66—C65−0.8 (3)
C32—C3—C4—C5−171.68 (12)C61—C62—C63—C640.4 (3)
N4—C4—C5—C6−124.15 (15)C62—C63—C64—C65−0.5 (3)
C3—C4—C5—C653.51 (15)C63—C64—C65—C660.0 (3)
C4—C5—C6—N1−53.75 (13)C64—C65—C66—C610.7 (3)
C4—C5—C6—C61−175.90 (10)
D—H···AD—HH···AD···AD—H···A
N5—H5···O14i0.89 (2)2.10 (2)2.9648 (17)167.1 (17)
C5—H5A···O14i0.972.563.4376 (17)151
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N5—H5⋯O14i0.89 (2)2.10 (2)2.9648 (17)167.1 (17)
C5—H5A⋯O14i0.972.563.4376 (17)151

Symmetry code: (i) .

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