Literature DB >> 21582594

1-Methyl-3,5-bis-[(E)-(3-methyl-2-thienyl)methyl-ene]piperidin-4-one monohydrate.

K Rajeswari, K Pandiarajan, P Gayathri, A Thiruvalluvar.   

Abstract

In the title mol-ecule, C(18)H(19)NOS(2)·H(2)O, the piperidine ring adopts an envelope conformation with the methyl substituent in an equatorial position. Each of the n class="Chemical">olefinic double bonds has an E configuration. The dihedral angle between the two thio-phene rings is 6.04 (14)°. The water mol-ecule forms two donor inter-actions, one with the carbonyl O atom and the other to the hetero N atom. The centrosymmetric {C(18)H(19)NOS(2)·H(2)O}(2) pairs thus formed are linked into a supra-molecular chain via C-H⋯O(water) contacts.

Entities:  

Year:  2009        PMID： 21582594      PMCID： PMC2968964          DOI： 10.1107/S1600536809010393

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


Related literature

For piperidine-4-ones as anti­mycobacterial agents, see: Jha & Dimmock (2006 ▶). For their cytotoxic properties, see: Das et al. (2007 ▶).

Experimental

Crystal data

C18H19NOS2·n class="Chemical">H2O M = 347.50 Triclinic, a = 7.5781 (7) Å b = 10.9926 (9) Å c = 11.5304 (10) Å α = 79.531 (2)° β = 83.404 (2)° γ = 71.673 (2)° V = 894.90 (14) Å3 Z = 2 Mo Kα radiation μ = 0.31 mm−1 T = 293 K 0.36 × 0.22 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.901, T max = 0.938 15827 measured reflections 3127 independent reflections 2686 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.130 S = 1.11 3127 reflections 217 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.44 e Å−3 Δρmin = −0.31 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/S1600536809010393/tk2393sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010393/tk2393Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H19NOS2·H2OZ = 2
Mr = 347.50F(000) = 368
Triclinic, P1Dx = 1.290 Mg m−3
Hall symbol: -P 1Melting point: 423 K
a = 7.5781 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9926 (9) ÅCell parameters from 9874 reflections
c = 11.5304 (10) Åθ = 2.0–25.0°
α = 79.531 (2)°µ = 0.31 mm−1
β = 83.404 (2)°T = 293 K
γ = 71.673 (2)°Prism, colourless
V = 894.90 (14) Å30.36 × 0.22 × 0.22 mm
Bruker Kappa APEXII CCD diffractometer3127 independent reflections
Radiation source: fine-focus sealed tube2686 reflections with I > 2σ(I)
graphiteRint = 0.021
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 2.0°
ω and φ scansh = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)k = −13→13
Tmin = 0.901, Tmax = 0.938l = −13→13
15827 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0602P)2 + 0.4317P] where P = (Fo2 + 2Fc2)/3
3127 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.44 e Å−3
3 restraintsΔρmin = −0.31 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
S310.12090 (9)0.66376 (7)0.92973 (5)0.0616 (2)
S510.60928 (9)0.12751 (6)0.41757 (6)0.0613 (2)
O40.1381 (3)0.60702 (18)0.46923 (16)0.0789 (7)
N10.3386 (3)0.31766 (17)0.73473 (15)0.0491 (6)
C20.3009 (4)0.4473 (2)0.7629 (2)0.0561 (8)
C30.1977 (3)0.5506 (2)0.67020 (19)0.0481 (7)
C40.2189 (3)0.5242 (2)0.54771 (19)0.0517 (7)
C50.3416 (3)0.3973 (2)0.52192 (19)0.0491 (7)
C60.4442 (3)0.3036 (2)0.6214 (2)0.0562 (8)
C110.4415 (4)0.2222 (3)0.8279 (2)0.0644 (9)
C130.0932 (3)0.6700 (2)0.6881 (2)0.0496 (7)
C150.3552 (3)0.3766 (2)0.40958 (19)0.0503 (7)
C320.0478 (3)0.7334 (2)0.7898 (2)0.0508 (7)
C33−0.0590 (3)0.8610 (2)0.7893 (2)0.0580 (8)
C34−0.0799 (4)0.8984 (3)0.9011 (3)0.0717 (10)
C350.0091 (4)0.8029 (3)0.9852 (3)0.0747 (11)
C36−0.1438 (4)0.9519 (3)0.6826 (3)0.0700 (9)
C520.4595 (3)0.2700 (2)0.3507 (2)0.0520 (8)
C530.4559 (3)0.2664 (3)0.2315 (2)0.0564 (8)
C540.5707 (4)0.1487 (3)0.1991 (2)0.0660 (9)
C550.6615 (4)0.0657 (3)0.2886 (3)0.0688 (10)
C560.3477 (4)0.3754 (3)0.1436 (2)0.0733 (10)
O1W0.0177 (4)0.2338 (3)0.7303 (2)0.1048 (11)
H2A0.417930.461990.772000.0673*
H2B0.228270.453490.837750.0673*
H6A0.468570.215720.606100.0675*
H6B0.563080.318110.625160.0675*
H11A0.556530.238810.834940.0966*
H11B0.467320.136700.808580.0966*
H11C0.368290.228280.901530.0966*
H130.039310.721880.620500.0595*
H150.281750.445740.359910.0604*
H34−0.148370.981020.916130.0860*
H350.008910.812271.063750.0897*
H36A−0.059850.935300.614290.1049*
H36B−0.166381.039850.694440.1049*
H36C−0.259320.938600.670700.1049*
H540.582820.129870.122610.0792*
H550.74340−0.016050.281080.0825*
H56A0.260730.440020.184850.1096*
H56B0.281370.342200.097100.1096*
H56C0.432050.413570.092670.1096*
H1A0.099 (5)0.273 (4)0.734 (4)0.1573*
H1B−0.046 (5)0.280 (4)0.672 (3)0.1573*
U11U22U33U12U13U23
S310.0677 (4)0.0680 (4)0.0491 (4)−0.0236 (3)−0.0051 (3)−0.0026 (3)
S510.0647 (4)0.0559 (4)0.0604 (4)−0.0181 (3)−0.0016 (3)−0.0035 (3)
O40.0979 (14)0.0685 (12)0.0485 (10)0.0049 (10)−0.0227 (10)0.0036 (9)
N10.0583 (11)0.0452 (10)0.0402 (9)−0.0132 (8)−0.0086 (8)0.0021 (8)
C20.0684 (15)0.0514 (13)0.0466 (12)−0.0150 (11)−0.0143 (11)−0.0016 (10)
C30.0477 (12)0.0487 (12)0.0466 (12)−0.0157 (10)−0.0068 (9)0.0008 (9)
C40.0536 (13)0.0521 (13)0.0446 (12)−0.0123 (10)−0.0099 (10)0.0025 (10)
C50.0491 (12)0.0531 (12)0.0436 (11)−0.0169 (10)−0.0050 (9)0.0003 (9)
C60.0559 (14)0.0571 (14)0.0469 (12)−0.0084 (11)−0.0046 (10)−0.0002 (10)
C110.0805 (18)0.0536 (14)0.0501 (13)−0.0102 (12)−0.0153 (12)0.0041 (11)
C130.0463 (12)0.0500 (12)0.0493 (12)−0.0143 (10)−0.0070 (9)0.0025 (10)
C150.0509 (12)0.0545 (13)0.0444 (12)−0.0182 (10)−0.0071 (9)0.0021 (10)
C320.0451 (12)0.0544 (13)0.0522 (13)−0.0176 (10)−0.0021 (10)−0.0021 (10)
C330.0458 (12)0.0588 (14)0.0672 (15)−0.0147 (10)0.0035 (11)−0.0106 (12)
C340.0656 (16)0.0710 (17)0.0754 (18)−0.0145 (14)0.0074 (14)−0.0215 (14)
C350.0772 (19)0.093 (2)0.0607 (16)−0.0330 (16)0.0111 (14)−0.0255 (15)
C360.0591 (15)0.0571 (15)0.0807 (18)−0.0026 (12)−0.0072 (13)−0.0027 (13)
C520.0513 (13)0.0602 (14)0.0497 (12)−0.0272 (11)−0.0026 (10)−0.0036 (10)
C530.0563 (14)0.0712 (15)0.0519 (13)−0.0328 (12)−0.0003 (10)−0.0129 (11)
C540.0687 (16)0.0806 (18)0.0608 (15)−0.0361 (14)0.0044 (13)−0.0224 (14)
C550.0650 (16)0.0635 (16)0.0848 (19)−0.0271 (13)0.0106 (14)−0.0246 (14)
C560.0785 (18)0.099 (2)0.0501 (14)−0.0375 (16)−0.0123 (13)−0.0066 (14)
O1W0.114 (2)0.126 (2)0.0823 (15)−0.0674 (16)−0.0458 (14)0.0452 (14)
S31—C321.728 (2)C53—C561.506 (4)
S31—C351.698 (3)C53—C541.401 (4)
S51—C521.726 (2)C54—C551.341 (4)
S51—C551.701 (3)C2—H2A0.9700
O4—C41.225 (3)C2—H2B0.9700
O1W—H1A0.86 (4)C6—H6B0.9700
O1W—H1B0.86 (4)C6—H6A0.9700
N1—C111.460 (3)C11—H11C0.9600
N1—C21.452 (3)C11—H11B0.9600
N1—C61.459 (3)C11—H11A0.9600
C2—C31.495 (3)C13—H130.9300
C3—C41.474 (3)C15—H150.9300
C3—C131.342 (3)C34—H340.9300
C4—C51.473 (3)C35—H350.9300
C5—C151.342 (3)C36—H36A0.9600
C5—C61.501 (3)C36—H36C0.9600
C13—C321.426 (3)C36—H36B0.9600
C15—C521.429 (3)C54—H540.9300
C32—C331.381 (3)C55—H550.9300
C33—C341.400 (4)C56—H56C0.9600
C33—C361.502 (4)C56—H56A0.9600
C34—C351.354 (5)C56—H56B0.9600
C52—C531.386 (3)
S31···C23.200 (2)C54···H36Ciii2.9700
S31···C54i3.611 (3)C55···H36Ciii3.0400
S51···C63.208 (2)C56···H152.6900
S51···C13i3.614 (2)H1A···N12.03 (4)
S51···C36ii3.669 (3)H1A···C22.88 (4)
S31···H56Biii3.1200H1A···H35iv2.5000
S31···H2B2.5800H1A···C112.78 (4)
S51···H6A2.5300H1A···C62.87 (4)
O1W···N12.867 (4)H1B···O4iii1.91 (4)
O1W···O4iii2.759 (3)H2A···H11A2.3600
O1W···C35iv3.222 (4)H2A···H6B2.4600
O4···O1Wiii2.759 (3)H2B···C322.9200
O1W···H55v2.5200H2B···H11C2.3800
O1W···H35iv2.3400H2B···S312.5800
O4···H152.2800H6A···S512.5300
O4···H132.2600H6A···H11B2.3400
O4···H6Bi2.7000H6A···C522.9000
O4···H1Biii1.91 (4)H6B···H11A2.4200
N1···O1W2.867 (4)H6B···H2A2.4600
N1···H1A2.03 (4)H6B···O4i2.7000
C2···S313.200 (2)H6B···C4i3.0800
C6···S513.208 (2)H11A···H2A2.3600
C13···S51i3.614 (2)H11A···H6B2.4200
C32···C55i3.525 (4)H11B···H6A2.3400
C32···C56iii3.521 (4)H11C···H2B2.3800
C32···C54i3.543 (4)H11C···C35iv3.1000
C33···C55i3.342 (4)H13···C362.6600
C35···O1Wiv3.222 (4)H13···H36A2.2200
C36···S51vi3.669 (3)H13···O42.2600
C54···C32i3.543 (4)H15···O42.2800
C54···S31i3.611 (3)H15···C562.6900
C55···C32i3.525 (4)H15···H56A2.0600
C55···C33i3.342 (4)H34···H36B2.5300
C56···C32iii3.521 (4)H35···H1Aiv2.5000
C2···H1A2.88 (4)H35···O1Wiv2.3400
C4···H6Bi3.0800H36A···C132.7900
C6···H1A2.87 (4)H36A···H132.2200
C11···H1A2.78 (4)H36B···H342.5300
C13···H36A2.7900H36C···C55iii3.0400
C15···H56A2.6800H36C···C53iii3.0600
C32···H2B2.9200H36C···C54iii2.9700
C32···H56Biii2.9600H55···O1Wv2.5200
C35···H11Civ3.1000H56A···H152.0600
C36···H132.6600H56A···C152.6800
C52···H6A2.9000H56B···S31iii3.1200
C53···H36Ciii3.0600H56B···C32iii2.9600
C32—S31—C3592.06 (14)H2A—C2—H2B108.00
C52—S51—C5591.93 (14)C3—C2—H2A109.00
H1A—O1W—H1B104 (4)N1—C6—H6A109.00
C2—N1—C6111.48 (18)C5—C6—H6A109.00
C2—N1—C11109.72 (19)C5—C6—H6B109.00
C6—N1—C11109.73 (19)N1—C6—H6B109.00
N1—C2—C3112.71 (19)H6A—C6—H6B108.00
C2—C3—C4118.61 (19)N1—C11—H11B109.00
C2—C3—C13125.0 (2)N1—C11—H11C109.00
C4—C3—C13116.3 (2)H11A—C11—H11B109.00
O4—C4—C3120.4 (2)H11A—C11—H11C109.00
O4—C4—C5121.1 (2)H11B—C11—H11C109.00
C3—C4—C5118.50 (19)N1—C11—H11A109.00
C4—C5—C15116.6 (2)C3—C13—H13113.00
C6—C5—C15125.4 (2)C32—C13—H13114.00
C4—C5—C6117.98 (18)C52—C15—H15113.00
N1—C6—C5111.81 (19)C5—C15—H15113.00
C3—C13—C32133.0 (2)C33—C34—H34123.00
C5—C15—C52133.1 (2)C35—C34—H34123.00
S31—C32—C33110.37 (17)C34—C35—H35124.00
C13—C32—C33124.3 (2)S31—C35—H35124.00
S31—C32—C13125.32 (17)C33—C36—H36A109.00
C32—C33—C36125.1 (2)C33—C36—H36C109.00
C34—C33—C36122.7 (2)H36A—C36—H36B109.00
C32—C33—C34112.2 (2)H36A—C36—H36C109.00
C33—C34—C35113.6 (3)H36B—C36—H36C109.00
S31—C35—C34111.7 (3)C33—C36—H36B110.00
S51—C52—C15124.92 (17)C55—C54—H54123.00
S51—C52—C53110.18 (18)C53—C54—H54123.00
C15—C52—C53124.9 (2)S51—C55—H55124.00
C52—C53—C56125.4 (3)C54—C55—H55124.00
C54—C53—C56122.5 (2)C53—C56—H56B109.00
C52—C53—C54112.1 (2)C53—C56—H56C109.00
C53—C54—C55113.8 (2)C53—C56—H56A110.00
S51—C55—C54112.0 (2)H56A—C56—H56C109.00
N1—C2—H2A109.00H56B—C56—H56C109.00
N1—C2—H2B109.00H56A—C56—H56B109.00
C3—C2—H2B109.00
C35—S31—C32—C13179.2 (2)C4—C5—C6—N131.7 (3)
C35—S31—C32—C330.3 (2)C15—C5—C6—N1−150.0 (2)
C32—S31—C35—C34−0.1 (3)C4—C5—C15—C52178.7 (2)
C55—S51—C52—C15179.7 (2)C6—C5—C15—C520.3 (4)
C55—S51—C52—C53−0.7 (2)C3—C13—C32—S31−1.2 (4)
C52—S51—C55—C540.2 (3)C3—C13—C32—C33177.5 (3)
C6—N1—C2—C357.5 (3)C5—C15—C52—S51−0.2 (4)
C11—N1—C2—C3179.2 (2)C5—C15—C52—C53−179.8 (3)
C2—N1—C6—C5−59.9 (3)S31—C32—C33—C34−0.5 (3)
C11—N1—C6—C5178.4 (2)S31—C32—C33—C36179.2 (2)
N1—C2—C3—C4−26.9 (3)C13—C32—C33—C34−179.4 (2)
N1—C2—C3—C13156.9 (2)C13—C32—C33—C360.2 (4)
C2—C3—C4—O4−179.2 (2)C32—C33—C34—C350.4 (4)
C2—C3—C4—C5−0.3 (3)C36—C33—C34—C35−179.2 (3)
C13—C3—C4—O4−2.7 (4)C33—C34—C35—S31−0.2 (4)
C13—C3—C4—C5176.3 (2)S51—C52—C53—C541.1 (3)
C2—C3—C13—C32−0.3 (4)S51—C52—C53—C56−177.2 (2)
C4—C3—C13—C32−176.6 (2)C15—C52—C53—C54−179.3 (2)
O4—C4—C5—C6176.6 (2)C15—C52—C53—C562.4 (4)
O4—C4—C5—C15−1.9 (4)C52—C53—C54—C55−1.0 (4)
C3—C4—C5—C6−2.3 (3)C56—C53—C54—C55177.4 (3)
C3—C4—C5—C15179.2 (2)C53—C54—C55—S510.4 (4)
D—H···AD—HH···AD···AD—H···A
O1W—H1A···N10.86 (4)2.03 (4)2.867 (4)164 (4)
O1W—H1B···O4iii0.86 (4)1.91 (4)2.759 (3)167 (4)
C2—H2B···S310.972.583.200 (2)122
C6—H6A···S510.972.533.208 (2)127
C13—H13···O40.932.262.693 (3)108
C15—H15···O40.932.282.711 (3)108
C35—H35···O1Wiv0.932.343.222 (4)159
C55—H55···O1Wv0.932.523.450 (4)176
C56—H56B···Cg(1)iii0.962.973.763 (3)141
C36—H36C···Cg(2)iii0.962.833.742 (3)159
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1W—H1A⋯N10.86 (4)2.03 (4)2.867 (4)164 (4)
O1W—H1B⋯O4i0.86 (4)1.91 (4)2.759 (3)167 (4)
C2—H2B⋯S310.972.583.200 (2)122
C6—H6A⋯S510.972.533.208 (2)127
C13—H13⋯O40.932.262.693 (3)108
C15—H15⋯O40.932.282.711 (3)108
C35—H35⋯O1Wii0.932.343.222 (4)159
C55—H55⋯O1Wiii0.932.523.450 (4)176
C56—H56B⋯Cg1i0.962.973.763 (3)141
C36—H36C⋯Cg2i0.962.833.742 (3)159

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the S31/C32–C35 and S51/C52–C55 rings ,respectively.

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Authors:  A Jha; J R Dimmock
Journal:  Pharmazie       Date:  2006-06       Impact factor: 1.267

3.  Design, synthesis and cytotoxic properties of novel 1-[4-(2-alkylaminoethoxy)phenylcarbonyl]-3,5-bis(arylidene)-4-piperidones and related compounds.

Authors:  Umashankar Das; Jane Alcorn; Anuraag Shrivastav; Rajendra K Sharma; Erik De Clercq; Jan Balzarini; Jonathan R Dimmock
Journal:  Eur J Med Chem       Date:  2006-09-22       Impact factor: 6.514

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  1 in total

1.  1-Benzyl-3,5-bis-[(E)-3-thienyl-methyl-idene]piperidin-4-one.

Authors:  P Gayathri; A Thiruvalluvar; K Rajeswari; K Pandiarajan; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-05
  1 in total

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