Literature DB >> 21579416

4-[(2E)-2-(4-Chloro-benzyl-idene)hydrazinyl-idene]-1-methyl-1,4-dihydro-pyridine monohydrate.

Abdullah Aydın, Mehmet Akkurt, Vildan Alptüzün, Orhan Büyükgüngör, Ulrike Holzgrabe, Krzysztof Radacki.   

Abstract

In the title compound, C(13)H(12)ClN(3)·H(2)O, the organic mol-ecule is almost planar, with a dihedral angle of 3.22 (10)° between the benzene and pyridine rings. The crystal structure is stabilized by O-H⋯N and C-H⋯O hydrogen bonding and π-π stacking inter-actions [centroid-centroid distances = 3.630 (1) and 3.701 (1) Å].

Entities:  

Year:  2010        PMID： 21579416      PMCID： PMC2979526          DOI： 10.1107/S1600536810015709

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


Related literature

For the synthesis and pharmacological activity of (benzyl­idene-hydrazono)-1,4-dihydro­pyridine derivatives, see: Douglas et al. (1977 ▶); Alptüzün et al. (2010 ▶); Savini et al. (2002 ▶); Pandey et al. (2002 ▶); Salgın-Gökşen et al. (2007 ▶); Silva et al. (2004 ▶); Vicini et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶); Diao et al. (2008 ▶); Odabaşoğlu et al. (2003 ▶). For quantum-chemical calculations, see: Pople & Beveridge (1970 ▶).

Experimental

Crystal data

C13H12ClN3·H2O M = 263.72 Monoclinic, a = 5.8492 (4) Å b = 20.3101 (10) Å c = 12.2035 (7) Å β = 113.855 (4)° V = 1325.90 (14) Å3 Z = 4 Mo Kα radiation μ = 0.28 mm−1 T = 296 K 0.60 × 0.30 × 0.04 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.905, T max = 0.989 14028 measured reflections 2759 independent reflections 1746 reflections with I > 2σ(I) R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.095 S = 0.95 2759 reflections 170 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.16 e Å−3 Δρmin = −0.18 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015709/sj2782sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015709/sj2782Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H12ClN3·H2OF(000) = 552
Mr = 263.72Dx = 1.321 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11448 reflections
a = 5.8492 (4) Åθ = 1.8–27.3°
b = 20.3101 (10) ŵ = 0.28 mm−1
c = 12.2035 (7) ÅT = 296 K
β = 113.855 (4)°Needle, yellow
V = 1325.90 (14) Å30.60 × 0.30 × 0.04 mm
Z = 4
Stoe IPDS 2 diffractometer2759 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1746 reflections with I > 2σ(I)
plane graphiteRint = 0.064
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 2.0°
ω scansh = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −25→25
Tmin = 0.905, Tmax = 0.989l = −15→15
14028 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 0.95w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3
2759 reflections(Δ/σ)max < 0.001
170 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.18 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 esds 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
Cl11.22894 (12)0.72508 (3)0.80784 (5)0.0626 (2)
N10.3123 (3)0.56701 (10)0.35465 (13)0.0453 (6)
N20.0774 (3)0.54841 (9)0.27204 (13)0.0441 (6)
N30.0599 (4)0.39257 (9)0.05147 (14)0.0478 (6)
C10.5371 (4)0.63831 (11)0.52012 (15)0.0414 (7)
C20.5222 (4)0.69371 (12)0.58483 (16)0.0452 (7)
C30.7336 (4)0.72021 (11)0.67306 (16)0.0466 (7)
C40.9614 (4)0.69105 (12)0.69752 (16)0.0449 (7)
C50.9807 (4)0.63606 (12)0.63540 (16)0.0460 (8)
C60.7697 (4)0.60996 (12)0.54740 (16)0.0460 (7)
C70.3079 (4)0.61193 (11)0.42743 (16)0.0435 (7)
C80.0859 (4)0.49832 (11)0.20400 (15)0.0396 (7)
C90.3019 (4)0.46263 (11)0.21152 (16)0.0437 (7)
C100.2819 (4)0.41223 (12)0.13694 (18)0.0480 (7)
C11−0.1504 (4)0.42521 (12)0.04046 (17)0.0473 (7)
C12−0.1430 (4)0.47578 (12)0.11261 (16)0.0449 (7)
C130.0497 (5)0.33651 (13)−0.0272 (2)0.0668 (10)
O10.6224 (4)0.61903 (10)0.21954 (15)0.0611 (7)
H20.367500.713000.568100.0540*
H30.722400.757300.715400.0560*
H51.135900.616800.653000.0550*
H60.782800.572900.505600.0550*
H70.154500.628200.421100.0520*
H90.458300.474400.268700.0520*
H100.426200.389900.144200.0580*
H11−0.303300.41230−0.018400.0570*
H12−0.291400.496800.102800.0540*
H13A0.180000.34090−0.055500.1000*
H13B−0.109700.33600−0.094200.1000*
H13C0.072000.296200.017000.1000*
H1A0.551 (6)0.6046 (17)0.262 (2)0.0920*
H1B0.768 (6)0.5959 (17)0.242 (2)0.0920*
U11U22U33U12U13U23
Cl10.0551 (4)0.0646 (4)0.0574 (3)−0.0114 (3)0.0116 (2)−0.0153 (3)
N10.0411 (10)0.0499 (12)0.0415 (8)−0.0024 (9)0.0133 (7)−0.0039 (8)
N20.0365 (10)0.0484 (12)0.0446 (8)−0.0022 (9)0.0135 (7)−0.0053 (8)
N30.0558 (12)0.0433 (12)0.0455 (9)−0.0060 (10)0.0216 (8)−0.0054 (8)
C10.0461 (13)0.0438 (13)0.0351 (9)−0.0015 (11)0.0173 (9)0.0023 (8)
C20.0453 (13)0.0457 (14)0.0446 (10)0.0042 (11)0.0182 (9)0.0017 (9)
C30.0577 (14)0.0395 (13)0.0434 (10)0.0004 (12)0.0212 (10)−0.0043 (9)
C40.0472 (13)0.0469 (14)0.0387 (10)−0.0069 (11)0.0154 (9)0.0011 (9)
C50.0431 (13)0.0481 (15)0.0456 (11)0.0046 (11)0.0167 (10)−0.0020 (9)
C60.0485 (14)0.0474 (14)0.0406 (10)0.0035 (11)0.0164 (9)−0.0065 (9)
C70.0422 (12)0.0473 (14)0.0429 (10)0.0003 (11)0.0191 (9)−0.0014 (9)
C80.0393 (12)0.0407 (13)0.0388 (9)−0.0004 (10)0.0158 (8)0.0028 (9)
C90.0374 (12)0.0458 (14)0.0428 (10)−0.0013 (10)0.0110 (9)0.0001 (9)
C100.0456 (13)0.0460 (14)0.0545 (11)0.0041 (11)0.0223 (10)0.0025 (10)
C110.0424 (13)0.0503 (15)0.0437 (10)−0.0070 (12)0.0118 (9)−0.0004 (10)
C120.0357 (12)0.0511 (15)0.0439 (10)−0.0021 (11)0.0120 (9)−0.0015 (9)
C130.084 (2)0.0570 (17)0.0615 (14)−0.0065 (15)0.0316 (14)−0.0174 (12)
O10.0514 (11)0.0661 (13)0.0668 (10)0.0032 (9)0.0250 (8)0.0088 (8)
Cl1—C41.742 (2)C8—C91.427 (3)
O1—H1B0.91 (4)C8—C121.428 (3)
O1—H1A0.84 (3)C9—C101.343 (3)
N1—N21.388 (2)C11—C121.342 (3)
N1—C71.281 (3)C2—H20.9300
N2—C81.327 (3)C3—H30.9300
N3—C101.356 (3)C5—H50.9300
N3—C111.355 (3)C6—H60.9300
N3—C131.475 (3)C7—H70.9300
C1—C21.398 (3)C9—H90.9300
C1—C71.462 (3)C10—H100.9300
C1—C61.388 (3)C11—H110.9300
C2—C31.379 (3)C12—H120.9300
C3—C41.376 (3)C13—H13C0.9600
C4—C51.380 (3)C13—H13A0.9600
C5—C61.373 (3)C13—H13B0.9600
Cl1···C2i3.521 (2)C11···C8iv3.516 (3)
Cl1···C7i3.572 (2)C11···O1iv3.378 (3)
Cl1···H10ii2.9800C13···C4xi3.598 (3)
O1···N2iii2.859 (3)C13···C3xi3.490 (4)
O1···C11iv3.378 (3)C3···H13Ax2.9800
O1···N13.089 (3)C7···H1Bvii3.07 (3)
O1···H13Biv2.9100C7···H1A2.91 (3)
O1···H3v2.5800C8···H1Bvii2.88 (4)
O1···H11iv2.4900C12···H1Bvii3.06 (3)
O1···H13Avi2.8100H1A···N12.26 (3)
N1···O13.089 (3)H1A···C72.91 (3)
N2···O1vii2.859 (3)H1B···H12iii2.5700
N1···H1A2.26 (3)H1B···N2iii1.95 (4)
N1···H62.6200H1B···C7iii3.07 (3)
N1···H92.4700H1B···C8iii2.88 (4)
N2···H1Bvii1.95 (4)H1B···C12iii3.06 (3)
C2···Cl1viii3.521 (2)H1B···H7iii2.5100
C3···C10ix3.576 (3)H2···H72.4300
C3···C13x3.490 (4)H3···O1xii2.5800
C4···C13x3.598 (3)H6···N12.6200
C4···C10ix3.582 (3)H7···H1Bvii2.5100
C5···C8ix3.473 (3)H7···H22.4300
C5···C9ix3.569 (3)H9···N12.4700
C6···C9ix3.464 (3)H10···H13A2.4800
C6···C8ix3.561 (3)H10···Cl1ii2.9800
C7···Cl1viii3.572 (2)H11···H13B2.3200
C8···C11iv3.516 (3)H11···O1iv2.4900
C8···C6ix3.561 (3)H12···H1Bvii2.5700
C8···C5ix3.473 (3)H13A···H102.4800
C9···C5ix3.569 (3)H13A···C3xi2.9800
C9···C6ix3.464 (3)H13A···O1vi2.8100
C10···C4ix3.582 (3)H13B···H112.3200
C10···C3ix3.576 (3)H13B···O1iv2.9100
H1A—O1—H1B106 (3)C1—C2—H2120.00
N2—N1—C7113.95 (19)C3—C2—H2120.00
N1—N2—C8112.75 (18)C4—C3—H3120.00
C10—N3—C13120.1 (2)C2—C3—H3120.00
C11—N3—C13121.1 (2)C4—C5—H5120.00
C10—N3—C11118.73 (19)C6—C5—H5120.00
C2—C1—C6118.52 (19)C5—C6—H6120.00
C6—C1—C7122.5 (2)C1—C6—H6120.00
C2—C1—C7119.0 (2)N1—C7—H7119.00
C1—C2—C3121.0 (2)C1—C7—H7119.00
C2—C3—C4119.0 (2)C10—C9—H9120.00
Cl1—C4—C5119.88 (18)C8—C9—H9120.00
C3—C4—C5121.1 (2)N3—C10—H10119.00
Cl1—C4—C3119.03 (17)C9—C10—H10119.00
C4—C5—C6119.7 (2)C12—C11—H11119.00
C1—C6—C5120.7 (2)N3—C11—H11119.00
N1—C7—C1121.9 (2)C8—C12—H12119.00
N2—C8—C12118.3 (2)C11—C12—H12119.00
C9—C8—C12114.43 (19)N3—C13—H13B109.00
N2—C8—C9127.27 (19)N3—C13—H13C109.00
C8—C9—C10120.8 (2)N3—C13—H13A109.00
N3—C10—C9122.7 (2)H13A—C13—H13C110.00
N3—C11—C12121.5 (2)H13B—C13—H13C110.00
C8—C12—C11122.0 (2)H13A—C13—H13B109.00
C7—N1—N2—C8−174.99 (18)C6—C1—C7—N1−10.1 (3)
N2—N1—C7—C1−179.43 (18)C1—C2—C3—C4−0.4 (3)
N1—N2—C8—C12−178.00 (18)C2—C3—C4—C50.0 (3)
N1—N2—C8—C92.6 (3)C2—C3—C4—Cl1179.29 (17)
C13—N3—C11—C12179.2 (2)C3—C4—C5—C60.2 (3)
C10—N3—C11—C12−0.6 (3)Cl1—C4—C5—C6−179.11 (17)
C11—N3—C10—C90.3 (3)C4—C5—C6—C10.1 (3)
C13—N3—C10—C9−179.5 (2)N2—C8—C9—C10179.3 (2)
C2—C1—C6—C5−0.5 (3)N2—C8—C12—C11−179.7 (2)
C7—C1—C2—C3180.0 (2)C9—C8—C12—C11−0.2 (3)
C7—C1—C6—C5−179.8 (2)C12—C8—C9—C10−0.2 (3)
C2—C1—C7—N1170.6 (2)C8—C9—C10—N30.1 (3)
C6—C1—C2—C30.7 (3)N3—C11—C12—C80.5 (3)
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.84 (3)2.26 (3)3.089 (3)173 (3)
O1—H1B···N2iii0.91 (4)1.95 (4)2.859 (3)174 (2)
C3—H3···O1xii0.932.583.421 (3)150
C11—H11···O1iv0.932.493.378 (3)159
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1A⋯N10.84 (3)2.26 (3)3.089 (3)173 (3)
O1—H1B⋯N2i0.91 (4)1.95 (4)2.859 (3)174 (2)
C3—H3⋯O1ii0.932.583.421 (3)150
C11—H11⋯O1iii0.932.493.378 (3)159

Symmetry codes: (i) ; (ii) ; (iii) .

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