Literature DB >> 21582921

N'-(2-Methyl-3-phenyl-allyl-idene)nicotinohydrazide monohydrate.

R Archana, A Manimekalai, N Saradhadevi, A Thiruvalluvar, R J Butcher.   

Abstract

The asymmetric unit of the title compound, C(16)H(15)N(3)O·H(2)O, contains an N'-(2-methyl-3-phenyl-allyl-idene)nicotino-hydra-zide mol-ecule and a water solvent mol-ecule. The dihedral angle between the pyridine ring and the phenyl ring is 47.26 (5)°. Inter-molecular O-H⋯N, O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds are found in the crystal structure. Furthermore, C-H⋯π inter-actions involving the pyridine and phenyl rings are also found.

Entities:  

Year:  2009        PMID： 21582921      PMCID： PMC2969494          DOI： 10.1107/S1600536809023368

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


Related literature

For a related crystal structure, see: Bao (2008 ▶). For chemical and biological applications of related compounds, see: Moraweck et al. (1997 ▶); Kwon et al. (1996 ▶); Lee et al. (1999 ▶).

Experimental

Crystal data

C16H15N3O·n class="Chemical">H2O M = 283.33 Monoclinic, a = 9.6821 (4) Å b = 9.4178 (4) Å c = 16.0958 (6) Å β = 98.250 (4)° V = 1452.49 (10) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 110 K 0.51 × 0.42 × 0.36 mm

Data collection

Oxford Diffraction Gemini R diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.938, T max = 1.000 (expected range = 0.909–0.969) 10476 measured reflections 4824 independent reflections 3467 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.119 S = 1.02 4824 reflections 203 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.40 e Å−3 Δρmin = −0.22 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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/S1600536809023368/wn2333sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023368/wn2333Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H15N3O·H2OF(000) = 600
Mr = 283.33Dx = 1.296 Mg m−3
Monoclinic, P21/cMelting point: 400(2) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.6821 (4) ÅCell parameters from 4977 reflections
b = 9.4178 (4) Åθ = 4.6–32.6°
c = 16.0958 (6) ŵ = 0.09 mm−1
β = 98.250 (4)°T = 110 K
V = 1452.49 (10) Å3Block, colourless
Z = 40.51 × 0.42 × 0.36 mm
Oxford Diffraction Gemini R diffractometer4824 independent reflections
Radiation source: fine-focus sealed tube3467 reflections with I > 2σ(I)
graphiteRint = 0.021
Detector resolution: 10.5081 pixels mm-1θmax = 32.8°, θmin = 4.7°
φ and ω scansh = −14→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −12→14
Tmin = 0.938, Tmax = 1.000l = −17→24
10476 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0703P)2] where P = (Fo2 + 2Fc2)/3
4824 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.22 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
O7−0.01746 (7)0.46732 (8)0.12555 (4)0.0228 (2)
N1−0.32793 (9)0.63377 (9)−0.05360 (5)0.0216 (2)
N8−0.09368 (8)0.60130 (10)0.22771 (5)0.0191 (2)
N90.01977 (8)0.56186 (9)0.28577 (5)0.0201 (2)
C2−0.22360 (10)0.59151 (11)0.00496 (6)0.0189 (3)
C3−0.23120 (9)0.59362 (10)0.09091 (6)0.0163 (2)
C4−0.35482 (10)0.63912 (10)0.11676 (6)0.0186 (3)
C5−0.46492 (10)0.68046 (11)0.05655 (6)0.0205 (3)
C6−0.44662 (10)0.67645 (11)−0.02681 (6)0.0212 (3)
C7−0.10495 (10)0.54718 (10)0.14926 (6)0.0173 (2)
C100.02233 (10)0.61992 (11)0.35825 (6)0.0198 (3)
C110.13277 (10)0.58878 (10)0.42696 (6)0.0186 (2)
C120.12207 (10)0.65038 (10)0.50151 (6)0.0201 (3)
C130.24871 (12)0.49192 (13)0.41017 (7)0.0289 (3)
C210.21352 (10)0.63767 (10)0.58181 (6)0.0189 (3)
C220.30403 (11)0.52316 (11)0.60385 (6)0.0246 (3)
C230.39472 (12)0.52335 (13)0.67868 (7)0.0295 (3)
C240.39566 (11)0.63518 (14)0.73431 (6)0.0301 (3)
C250.30184 (11)0.74592 (13)0.71563 (7)0.0290 (3)
C260.21206 (10)0.74683 (12)0.64052 (6)0.0225 (3)
O1W0.23612 (8)0.34636 (8)0.21718 (5)0.0221 (2)
H2−0.140010.55834−0.012940.0227*
H4−0.363890.641910.174720.0223*
H5−0.550940.710840.072470.0246*
H6−0.522090.70546−0.067640.0254*
H8−0.1500 (15)0.6670 (15)0.2429 (8)0.035 (4)*
H10−0.049460.684550.367100.0238*
H120.043630.710850.501870.0241*
H13A0.336270.522390.443650.0434*
H13B0.258260.495650.350410.0434*
H13C0.227310.394480.425470.0434*
H220.303110.444360.566930.0295*
H230.456850.445890.691880.0354*
H240.459880.636230.784820.0361*
H250.299220.821390.754540.0348*
H260.148160.823180.628630.0270*
H1W0.2677 (16)0.3540 (16)0.1663 (11)0.054 (5)*
H2W0.1656 (18)0.4012 (18)0.2096 (10)0.055 (5)*
U11U22U33U12U13U23
O70.0208 (3)0.0255 (4)0.0221 (4)0.0058 (3)0.0028 (3)−0.0028 (3)
N10.0238 (4)0.0249 (4)0.0160 (4)0.0008 (3)0.0024 (3)−0.0009 (3)
N80.0159 (4)0.0244 (4)0.0161 (4)0.0031 (3)−0.0010 (3)−0.0029 (3)
N90.0176 (4)0.0237 (4)0.0179 (4)0.0010 (3)−0.0015 (3)0.0020 (3)
C20.0186 (4)0.0214 (5)0.0174 (4)−0.0001 (4)0.0048 (3)−0.0017 (4)
C30.0158 (4)0.0167 (4)0.0161 (4)−0.0016 (3)0.0018 (3)−0.0012 (3)
C40.0184 (4)0.0225 (5)0.0154 (4)−0.0014 (4)0.0040 (3)−0.0026 (3)
C50.0165 (4)0.0239 (5)0.0210 (5)0.0011 (4)0.0021 (3)−0.0034 (4)
C60.0196 (5)0.0239 (5)0.0188 (5)0.0014 (4)−0.0017 (3)−0.0014 (4)
C70.0162 (4)0.0183 (4)0.0173 (4)−0.0015 (3)0.0025 (3)−0.0005 (3)
C100.0175 (4)0.0213 (5)0.0198 (4)−0.0004 (4)−0.0003 (3)0.0000 (4)
C110.0178 (4)0.0189 (4)0.0186 (4)−0.0009 (3)0.0005 (3)0.0017 (4)
C120.0181 (4)0.0211 (5)0.0200 (4)0.0016 (4)−0.0010 (3)−0.0008 (4)
C130.0297 (6)0.0374 (6)0.0186 (5)0.0116 (5)0.0001 (4)−0.0012 (4)
C210.0170 (4)0.0216 (5)0.0180 (4)−0.0021 (4)0.0018 (3)0.0003 (4)
C220.0309 (5)0.0241 (5)0.0182 (5)0.0046 (4)0.0013 (4)0.0002 (4)
C230.0291 (5)0.0381 (6)0.0206 (5)0.0086 (5)0.0012 (4)0.0069 (4)
C240.0252 (5)0.0476 (7)0.0166 (5)−0.0022 (5)0.0003 (4)0.0008 (4)
C250.0274 (5)0.0393 (7)0.0205 (5)−0.0043 (5)0.0042 (4)−0.0087 (4)
C260.0199 (5)0.0272 (5)0.0207 (5)0.0011 (4)0.0040 (4)−0.0037 (4)
O1W0.0213 (4)0.0271 (4)0.0182 (3)0.0037 (3)0.0037 (3)0.0042 (3)
O7—C71.2336 (12)C21—C261.3978 (14)
O1W—H1W0.917 (17)C22—C231.3850 (15)
O1W—H2W0.851 (17)C23—C241.3816 (17)
N1—C21.3394 (13)C24—C251.3874 (17)
N1—C61.3455 (13)C25—C261.3841 (15)
N8—C71.3515 (13)C2—H20.9500
N8—N91.3868 (11)C4—H40.9500
N9—C101.2854 (13)C5—H50.9500
N8—H80.882 (14)C6—H60.9500
C2—C31.3960 (14)C10—H100.9500
C3—C71.4960 (13)C12—H120.9500
C3—C41.3901 (13)C13—H13A0.9800
C4—C51.3895 (14)C13—H13C0.9800
C5—C61.3789 (14)C13—H13B0.9800
C10—C111.4537 (14)C22—H220.9500
C11—C121.3501 (14)C23—H230.9500
C11—C131.5008 (15)C24—H240.9500
C12—C211.4630 (14)C25—H250.9500
C21—C221.4027 (14)C26—H260.9500
O1W···C10i3.3781 (13)C23···H4v2.8800
O1W···O72.9089 (10)C24···H4v3.0300
O1W···N93.2233 (11)C24···H5viii3.0900
O1W···C133.3815 (14)C25···H5viii2.9100
O1W···N1ii2.9033 (11)C26···H5viii2.7100
O1W···N8i2.8925 (12)H1W···C6ii3.040 (17)
O1W···C4i3.3753 (12)H1W···N1ii1.987 (17)
O7···O1W2.9089 (10)H1W···C2ii2.776 (17)
O7···C10i3.2830 (13)H2···O72.5200
O7···N92.7031 (10)H2···O7ii2.5400
O7···C2ii3.4021 (12)H2W···C72.994 (17)
O1W···H10i2.5900H2W···N92.507 (17)
O1W···H13B2.5500H2W···O72.161 (17)
O1W···H8i2.029 (14)H2W···H10i2.5600
O1W···H4i2.7700H2W···H13B2.4800
O7···H2ii2.5400H2W···H8i2.35 (2)
O7···H10i2.7400H4···N82.6600
O7···H22.5200H4···H23v2.5800
O7···H2W2.161 (17)H4···C24v3.0300
O7···H26iii2.5400H4···H82.2100
N1···O1Wii2.9033 (11)H4···O1Wiv2.7700
N8···O1Wiv2.8925 (12)H4···C23v2.8800
N9···O1W3.2233 (11)H5···C24ix3.0900
N9···O72.7031 (10)H5···C25ix2.9100
N1···H22iv2.9500H5···C26ix2.7100
N1···H1Wii1.987 (17)H5···C22ix2.9500
N8···H42.6600H5···C21ix2.7100
N9···H13B2.4700H6···H24vii2.4400
N9···H2W2.507 (17)H8···H2Wiv2.35 (2)
C2···O7ii3.4021 (12)H8···H42.2100
C4···C24v3.5844 (15)H8···C42.640 (14)
C4···C13iv3.5229 (15)H8···H102.1000
C4···O1Wiv3.3753 (12)H8···O1Wiv2.029 (14)
C5···C6vi3.4847 (15)H10···H82.1000
C5···C13iv3.5988 (16)H10···H2Wiv2.5600
C6···C5vi3.4847 (15)H10···H122.2400
C10···C21v3.5585 (14)H10···O1Wiv2.5900
C10···O7iv3.2830 (13)H10···O7iv2.7400
C10···O1Wiv3.3781 (13)H12···H262.3900
C10···C22v3.5673 (15)H12···H102.2400
C13···O1W3.3815 (14)H13A···C212.8800
C13···C5i3.5988 (16)H13A···C222.6400
C13···C4i3.5229 (15)H13A···H222.1800
C13···C223.1004 (15)H13B···O1W2.5500
C21···C10v3.5585 (14)H13B···N92.4700
C22···C133.1004 (15)H13B···H25iii2.3800
C22···C10v3.5673 (15)H13B···H2W2.4800
C24···C4v3.5844 (15)H13C···H222.3400
C2···H13Civ3.0700H13C···C2i3.0700
C2···H1Wii2.776 (17)H13C···C5i3.0400
C3···H13Civ2.8500H13C···C3i2.8500
C4···H13Civ2.8300H13C···C4i2.8300
C4···H82.640 (14)H22···H13A2.1800
C5···H13Civ3.0400H22···H13C2.3400
C6···H1Wii3.040 (17)H22···N1i2.9500
C6···H22iv3.0000H22···C6i3.0000
C6···H24vii3.0600H22···C112.9300
C7···H26iii2.8000H22···C132.5400
C7···H2W2.994 (17)H23···H4v2.5800
C11···H222.9300H24···C6x3.0600
C13···H222.5400H24···H6x2.4400
C21···H13A2.8800H25···H13Bxi2.3800
C21···H5viii2.7100H26···O7xi2.5400
C22···H13A2.6400H26···C7xi2.8000
C22···H5viii2.9500H26···H122.3900
H1W—O1W—H2W100.8 (15)C3—C2—H2118.00
C2—N1—C6117.12 (8)N1—C2—H2118.00
N9—N8—C7118.59 (8)C3—C4—H4120.00
N8—N9—C10114.07 (8)C5—C4—H4120.00
N9—N8—H8117.5 (9)C4—C5—H5121.00
C7—N8—H8123.6 (8)C6—C5—H5121.00
N1—C2—C3123.47 (9)C5—C6—H6118.00
C4—C3—C7124.28 (9)N1—C6—H6118.00
C2—C3—C4118.11 (9)N9—C10—H10119.00
C2—C3—C7117.61 (8)C11—C10—H10119.00
C3—C4—C5119.01 (9)C21—C12—H12115.00
C4—C5—C6118.57 (9)C11—C12—H12115.00
N1—C6—C5123.71 (9)C11—C13—H13A109.00
N8—C7—C3115.18 (8)C11—C13—H13C109.00
O7—C7—N8123.51 (9)H13A—C13—H13B109.00
O7—C7—C3121.30 (8)H13A—C13—H13C109.00
N9—C10—C11121.40 (9)H13B—C13—H13C109.00
C10—C11—C12116.59 (9)C11—C13—H13B109.00
C10—C11—C13118.24 (9)C23—C22—H22120.00
C12—C11—C13125.17 (9)C21—C22—H22120.00
C11—C12—C21129.50 (9)C22—C23—H23120.00
C22—C21—C26117.45 (9)C24—C23—H23120.00
C12—C21—C22124.28 (9)C25—C24—H24120.00
C12—C21—C26118.26 (9)C23—C24—H24120.00
C21—C22—C23120.93 (10)C24—C25—H25120.00
C22—C23—C24120.60 (11)C26—C25—H25120.00
C23—C24—C25119.30 (10)C21—C26—H26119.00
C24—C25—C26120.24 (10)C25—C26—H26119.00
C21—C26—C25121.33 (10)
C6—N1—C2—C3−1.84 (15)C4—C5—C6—N10.42 (16)
C2—N1—C6—C50.88 (15)N9—C10—C11—C12−177.04 (9)
C7—N8—N9—C10179.25 (9)N9—C10—C11—C132.96 (15)
N9—N8—C7—O7−2.13 (15)C10—C11—C12—C21178.57 (9)
N9—N8—C7—C3179.25 (8)C13—C11—C12—C21−1.43 (17)
N8—N9—C10—C11179.05 (9)C11—C12—C21—C22−22.57 (17)
N1—C2—C3—C41.46 (15)C11—C12—C21—C26156.91 (10)
N1—C2—C3—C7−178.27 (9)C12—C21—C22—C23175.37 (10)
C2—C3—C4—C5−0.06 (13)C26—C21—C22—C23−4.11 (15)
C7—C3—C4—C5179.65 (9)C12—C21—C26—C25−176.07 (10)
C2—C3—C7—O7−23.90 (14)C22—C21—C26—C253.45 (15)
C2—C3—C7—N8154.76 (9)C21—C22—C23—C241.54 (17)
C4—C3—C7—O7156.39 (10)C22—C23—C24—C251.83 (17)
C4—C3—C7—N8−24.94 (14)C23—C24—C25—C26−2.50 (17)
C3—C4—C5—C6−0.81 (15)C24—C25—C26—C21−0.20 (16)
D—H···AD—HH···AD···AD—H···A
O1W—H1W···N1ii0.917 (17)1.987 (17)2.9033 (11)177.3 (16)
O1W—H2W···O70.851 (17)2.161 (17)2.9089 (10)146.5 (15)
O1W—H2W···N90.851 (17)2.507 (17)3.2233 (11)142.5 (14)
N8—H8···O1Wiv0.882 (14)2.029 (14)2.8925 (12)166.0 (13)
C2—H2···O7ii0.952.543.4021 (12)151
C10—H10···O1Wiv0.952.593.3781 (13)140
C13—H13B···O1W0.982.553.3815 (14)143
C26—H26···O7xi0.952.543.4771 (13)170
C13—H13C···Cg1i0.982.723.5630 (13)144
C5—H5···Cg2ix0.952.573.4378 (11)152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1W—H1W⋯N1i0.917 (17)1.987 (17)2.9033 (11)177.3 (16)
O1W—H2W⋯O70.851 (17)2.161 (17)2.9089 (10)146.5 (15)
O1W—H2W⋯N90.851 (17)2.507 (17)3.2233 (11)142.5 (14)
N8—H8⋯O1Wii0.882 (14)2.029 (14)2.8925 (12)166.0 (13)
C2—H2⋯O7i0.952.543.4021 (12)151
C10—H10⋯O1Wii0.952.593.3781 (13)140
C13—H13B⋯O1W0.982.553.3815 (14)143
C26—H26⋯O7iii0.952.543.4771 (13)170
C13—H13C⋯Cg1iv0.982.723.5630 (13)144
C5—H5⋯Cg2v0.952.573.4378 (11)152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the pyridine and benzene rings, respectively.

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