Literature DB >> 21583957

(E)-N'-(2,5-Dimethoxy-benzyl-idene)-2-(8-quinol-yloxy)acetohydrazide methanol solvate.

Shou-Yu Wang, Liang Yuan, Liang Xu, Zhen Zhang, Yun-Peng Diao, De-Cheng Lv.   

Abstract

The two mol-ecules in the asymmetric unit of the title compound, C(20)H(19)N(3)O(4)·CH(4)O, are paired via O-H⋯(O,N), N-H⋯O, and C-H⋯O n class="Chemical">hydrogen bonds. The mol-ecular skeleton of the acetohydrazide mol-ecule is close to planar; the benzene and quinoline mean planes form a dihedral angle of 3.9 (3)°. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions, indicated by short distances of 3.668 (3) Å, between the centroids of N-containing six-membered rings from neighbouring acetohydrazide mol-ecules.

Entities:  

Year:  2009        PMID： 21583957      PMCID： PMC2977820          DOI： 10.1107/S1600536809015165

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


Related literature

For applications of 8-hydroxy­quinoline and its derivatives, see: Park et al. (2006 ▶); Karmakar et al. (2007 ▶). For a related structure, see Wen et al. (2005 ▶).

Experimental

Crystal data

C20H19N3O4·CH4O M = 397.42 Triclinic, a = 9.4199 (12) Å b = 10.8652 (14) Å c = 11.1721 (14) Å α = 93.268 (1)° β = 112.816 (2)° γ = 107.859 (3)° V = 982.8 (2) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 295 K 0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.985 5196 measured reflections 3456 independent reflections 2363 reflections with I > 2σ(I) R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.149 S = 1.03 3456 reflections 263 parameters H-atom parameters constrained Δρmax = 0.38 e Å−3 Δρmin = −0.33 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015165/cv2552sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015165/cv2552Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H19N3O4·CH4OZ = 2
Mr = 397.42F(000) = 420
Triclinic, P1Dx = 1.343 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4199 (12) ÅCell parameters from 1903 reflections
b = 10.8652 (14) Åθ = 2.5–26.9°
c = 11.1721 (14) ŵ = 0.10 mm−1
α = 93.268 (1)°T = 295 K
β = 112.816 (2)°Block, colorless
γ = 107.859 (3)°0.22 × 0.18 × 0.16 mm
V = 982.8 (2) Å3
Bruker SMART CCD area-detector diffractometer3456 independent reflections
Radiation source: fine-focus sealed tube2363 reflections with I > 2σ(I)
graphiteRint = 0.019
φ and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.979, Tmax = 0.985k = −12→12
5196 measured reflectionsl = −13→10
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0685P)2 + 0.304P] where P = (Fo2 + 2Fc2)/3
3456 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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 > σ(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
O1−0.24162 (17)0.13371 (15)0.32912 (13)0.0535 (4)
O20.0642 (2)0.1461 (2)0.64429 (16)0.0858 (6)
O30.4628 (2)0.39500 (19)0.28395 (18)0.0788 (5)
O40.8736 (2)0.3699 (2)0.7849 (2)0.0949 (7)
O5−0.0293 (3)0.2135 (3)0.1843 (2)0.1266 (11)
H5A−0.10810.23240.18180.190*
N1−0.3582 (2)0.19146 (18)0.08689 (17)0.0528 (5)
N20.0876 (2)0.19807 (18)0.45814 (17)0.0560 (5)
H20.03710.20200.37660.067*
N30.2580 (2)0.23818 (18)0.51768 (18)0.0558 (5)
C1−0.4175 (3)0.2184 (2)−0.0328 (2)0.0601 (6)
H1−0.34280.2594−0.06640.072*
C2−0.5851 (3)0.1892 (2)−0.1121 (2)0.0643 (7)
H2A−0.62030.2104−0.19560.077*
C3−0.6951 (3)0.1293 (2)−0.0644 (2)0.0627 (6)
H3−0.80730.1086−0.11540.075*
C4−0.6394 (3)0.0981 (2)0.0630 (2)0.0536 (6)
C5−0.7479 (3)0.0345 (3)0.1181 (3)0.0662 (7)
H5−0.86080.01410.07090.079*
C6−0.6890 (3)0.0033 (3)0.2383 (3)0.0693 (7)
H6−0.7616−0.03930.27310.083*
C7−0.5183 (3)0.0346 (2)0.3117 (2)0.0575 (6)
H7−0.47960.01160.39410.069*
C8−0.4090 (2)0.0981 (2)0.2636 (2)0.0474 (5)
C9−0.4680 (3)0.1308 (2)0.1355 (2)0.0473 (5)
C10−0.1828 (3)0.1048 (2)0.4579 (2)0.0543 (6)
H10A−0.22620.01010.45090.065*
H10B−0.22400.14500.51060.065*
C110.0023 (3)0.1532 (2)0.5280 (2)0.0549 (6)
C120.3277 (3)0.2839 (2)0.4443 (2)0.0603 (6)
H120.26220.28590.35760.072*
C130.5061 (3)0.3334 (2)0.4906 (2)0.0568 (6)
C140.5723 (3)0.3921 (2)0.4061 (3)0.0625 (6)
C150.7399 (4)0.4419 (3)0.4488 (3)0.0800 (8)
H150.78430.47980.39260.096*
C160.8436 (4)0.4366 (3)0.5739 (3)0.0842 (9)
H160.95720.47220.60200.101*
C170.7807 (3)0.3791 (3)0.6577 (3)0.0701 (7)
C180.6115 (3)0.3272 (2)0.6158 (3)0.0637 (6)
H180.56820.28790.67200.076*
C190.5240 (4)0.4653 (3)0.2014 (3)0.0892 (9)
H19A0.58710.55570.24600.134*
H19B0.43350.46160.12060.134*
H19C0.59310.42650.18140.134*
C201.0484 (4)0.4126 (4)0.8254 (4)0.1123 (12)
H20A1.07160.35720.77100.168*
H20B1.10200.40680.91640.168*
H20C1.08850.50230.81590.168*
C210.0330 (4)0.2797 (4)0.1045 (3)0.0957 (10)
H21A0.04940.37150.12450.144*
H21B−0.04320.24340.01330.144*
H21C0.13650.27050.11970.144*
U11U22U33U12U13U23
O10.0409 (8)0.0744 (10)0.0410 (8)0.0212 (7)0.0117 (7)0.0201 (7)
O20.0538 (10)0.1467 (18)0.0475 (10)0.0343 (11)0.0108 (8)0.0388 (11)
O30.0767 (12)0.0900 (13)0.0686 (12)0.0228 (10)0.0340 (10)0.0253 (10)
O40.0494 (11)0.1275 (18)0.0953 (15)0.0243 (11)0.0215 (10)0.0391 (13)
O50.0554 (12)0.231 (3)0.0757 (14)0.0286 (15)0.0217 (11)0.0755 (17)
N10.0500 (11)0.0604 (11)0.0436 (10)0.0208 (9)0.0143 (9)0.0138 (9)
N20.0412 (10)0.0703 (12)0.0432 (10)0.0135 (9)0.0089 (8)0.0160 (9)
N30.0412 (10)0.0607 (12)0.0548 (11)0.0126 (9)0.0139 (9)0.0118 (9)
C10.0621 (15)0.0668 (15)0.0468 (13)0.0245 (12)0.0164 (12)0.0188 (11)
C20.0704 (17)0.0686 (16)0.0465 (13)0.0317 (13)0.0112 (12)0.0177 (11)
C30.0519 (14)0.0673 (15)0.0549 (14)0.0260 (12)0.0052 (12)0.0122 (12)
C40.0458 (12)0.0561 (13)0.0493 (12)0.0219 (10)0.0083 (10)0.0069 (10)
C50.0405 (13)0.0817 (17)0.0658 (16)0.0215 (12)0.0121 (12)0.0161 (13)
C60.0475 (14)0.0895 (19)0.0670 (16)0.0188 (13)0.0245 (12)0.0199 (14)
C70.0506 (13)0.0723 (16)0.0487 (13)0.0231 (12)0.0186 (11)0.0167 (11)
C80.0396 (12)0.0538 (12)0.0434 (11)0.0181 (10)0.0115 (10)0.0068 (9)
C90.0452 (12)0.0485 (12)0.0431 (11)0.0191 (10)0.0124 (10)0.0071 (9)
C100.0471 (13)0.0720 (15)0.0431 (12)0.0235 (11)0.0154 (10)0.0214 (11)
C110.0467 (13)0.0679 (15)0.0437 (12)0.0211 (11)0.0117 (10)0.0174 (11)
C120.0515 (14)0.0667 (15)0.0543 (14)0.0162 (11)0.0181 (12)0.0106 (11)
C130.0510 (14)0.0536 (13)0.0624 (15)0.0152 (11)0.0240 (12)0.0073 (11)
C140.0608 (15)0.0559 (14)0.0722 (16)0.0179 (12)0.0324 (13)0.0094 (12)
C150.0690 (18)0.088 (2)0.094 (2)0.0265 (15)0.0457 (17)0.0337 (17)
C160.0548 (16)0.093 (2)0.108 (2)0.0191 (15)0.0427 (17)0.0303 (18)
C170.0496 (15)0.0756 (17)0.0789 (18)0.0232 (13)0.0203 (14)0.0169 (14)
C180.0540 (15)0.0660 (15)0.0709 (16)0.0177 (12)0.0292 (13)0.0139 (12)
C190.102 (2)0.088 (2)0.0793 (19)0.0258 (18)0.0458 (18)0.0277 (16)
C200.0522 (18)0.155 (3)0.114 (3)0.033 (2)0.0210 (18)0.041 (2)
C210.076 (2)0.121 (3)0.082 (2)0.0229 (18)0.0332 (17)0.0275 (19)
O1—C81.367 (2)C7—C81.364 (3)
O1—C101.420 (2)C7—H70.9300
O2—C111.219 (3)C8—C91.430 (3)
O3—C141.364 (3)C10—C111.504 (3)
O3—C191.410 (3)C10—H10A0.9700
O4—C171.378 (3)C10—H10B0.9700
O4—C201.435 (3)C12—C131.456 (3)
O5—C211.371 (3)C12—H120.9300
O5—H5A0.8200C13—C181.386 (3)
N1—C11.324 (3)C13—C141.403 (3)
N1—C91.363 (3)C14—C151.369 (4)
N2—C111.335 (3)C15—C161.378 (4)
N2—N31.385 (2)C15—H150.9300
N2—H20.8600C16—C171.374 (4)
N3—C121.271 (3)C16—H160.9300
C1—C21.398 (3)C17—C181.385 (3)
C1—H10.9300C18—H180.9300
C2—C31.355 (4)C19—H19A0.9600
C2—H2A0.9300C19—H19B0.9600
C3—C41.414 (3)C19—H19C0.9600
C3—H30.9300C20—H20A0.9600
C4—C91.411 (3)C20—H20B0.9600
C4—C51.415 (3)C20—H20C0.9600
C5—C61.348 (3)C21—H21A0.9600
C5—H50.9300C21—H21B0.9600
C6—C71.408 (3)C21—H21C0.9600
C6—H60.9300
C8—O1—C10115.50 (17)O2—C11—N2124.4 (2)
C14—O3—C19118.6 (2)O2—C11—C10117.6 (2)
C17—O4—C20116.1 (2)N2—C11—C10117.96 (18)
C21—O5—H5A109.5N3—C12—C13122.5 (2)
C1—N1—C9117.75 (19)N3—C12—H12118.7
C11—N2—N3119.67 (17)C13—C12—H12118.7
C11—N2—H2120.2C18—C13—C14119.4 (2)
N3—N2—H2120.2C18—C13—C12122.2 (2)
C12—N3—N2114.67 (19)C14—C13—C12118.4 (2)
N1—C1—C2124.2 (2)O3—C14—C15123.8 (2)
N1—C1—H1117.9O3—C14—C13116.8 (2)
C2—C1—H1117.9C15—C14—C13119.3 (3)
C3—C2—C1118.4 (2)C14—C15—C16120.8 (3)
C3—C2—H2A120.8C14—C15—H15119.6
C1—C2—H2A120.8C16—C15—H15119.6
C2—C3—C4120.1 (2)C17—C16—C15120.6 (3)
C2—C3—H3120.0C17—C16—H16119.7
C4—C3—H3120.0C15—C16—H16119.7
C9—C4—C3117.5 (2)C16—C17—O4125.0 (2)
C9—C4—C5119.7 (2)C16—C17—C18119.4 (3)
C3—C4—C5122.8 (2)O4—C17—C18115.5 (2)
C6—C5—C4120.5 (2)C17—C18—C13120.4 (2)
C6—C5—H5119.7C17—C18—H18119.8
C4—C5—H5119.7C13—C18—H18119.8
C5—C6—C7120.5 (2)O3—C19—H19A109.5
C5—C6—H6119.8O3—C19—H19B109.5
C7—C6—H6119.8H19A—C19—H19B109.5
C8—C7—C6121.0 (2)O3—C19—H19C109.5
C8—C7—H7119.5H19A—C19—H19C109.5
C6—C7—H7119.5H19B—C19—H19C109.5
C7—C8—O1124.68 (19)O4—C20—H20A109.5
C7—C8—C9119.8 (2)O4—C20—H20B109.5
O1—C8—C9115.50 (18)H20A—C20—H20B109.5
N1—C9—C4122.07 (19)O4—C20—H20C109.5
N1—C9—C8119.45 (18)H20A—C20—H20C109.5
C4—C9—C8118.5 (2)H20B—C20—H20C109.5
O1—C10—C11113.06 (18)O5—C21—H21A109.5
O1—C10—H10A109.0O5—C21—H21B109.5
C11—C10—H10A109.0H21A—C21—H21B109.5
O1—C10—H10B109.0O5—C21—H21C109.5
C11—C10—H10B109.0H21A—C21—H21C109.5
H10A—C10—H10B107.8H21B—C21—H21C109.5
C11—N2—N3—C12−177.4 (2)N3—N2—C11—O21.0 (4)
C9—N1—C1—C20.3 (3)N3—N2—C11—C10−177.22 (19)
N1—C1—C2—C3−0.1 (4)O1—C10—C11—O2172.0 (2)
C1—C2—C3—C40.2 (4)O1—C10—C11—N2−9.6 (3)
C2—C3—C4—C9−0.6 (3)N2—N3—C12—C13178.7 (2)
C2—C3—C4—C5−179.4 (2)N3—C12—C13—C183.6 (4)
C9—C4—C5—C6−0.9 (4)N3—C12—C13—C14−174.8 (2)
C3—C4—C5—C6177.9 (2)C19—O3—C14—C15−7.1 (4)
C4—C5—C6—C70.6 (4)C19—O3—C14—C13173.3 (2)
C5—C6—C7—C80.7 (4)C18—C13—C14—O3179.8 (2)
C6—C7—C8—O1179.0 (2)C12—C13—C14—O3−1.8 (3)
C6—C7—C8—C9−1.6 (3)C18—C13—C14—C150.2 (4)
C10—O1—C8—C7−2.3 (3)C12—C13—C14—C15178.6 (2)
C10—O1—C8—C9178.19 (18)O3—C14—C15—C16179.5 (3)
C1—N1—C9—C4−0.7 (3)C13—C14—C15—C16−0.9 (4)
C1—N1—C9—C8179.0 (2)C14—C15—C16—C171.1 (5)
C3—C4—C9—N10.8 (3)C15—C16—C17—O4−179.3 (3)
C5—C4—C9—N1179.7 (2)C15—C16—C17—C18−0.5 (4)
C3—C4—C9—C8−178.88 (19)C20—O4—C17—C16−6.5 (4)
C5—C4—C9—C80.0 (3)C20—O4—C17—C18174.7 (3)
C7—C8—C9—N1−178.5 (2)C16—C17—C18—C13−0.2 (4)
O1—C8—C9—N11.0 (3)O4—C17—C18—C13178.7 (2)
C7—C8—C9—C41.2 (3)C14—C13—C18—C170.4 (4)
O1—C8—C9—C4−179.29 (18)C12—C13—C18—C17−178.0 (2)
C8—O1—C10—C11−176.68 (18)
D—H···AD—HH···AD···AD—H···A
O5—H5A···O10.822.532.996 (3)117
O5—H5A···N10.822.062.782 (3)147
N2—H2···O50.862.012.856 (3)166
C12—H12···O50.932.513.305 (3)144
C3—H3···O2i0.932.603.220 (3)125
C20—H20A···O2ii0.962.593.511 (5)160
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O5—H5A⋯O10.822.532.996 (3)117
O5—H5A⋯N10.822.062.782 (3)147
N2—H2⋯O50.862.012.856 (3)166
C12—H12⋯O50.932.513.305 (3)144
C3—H3⋯O2i0.932.603.220 (3)125
C20—H20A⋯O2ii0.962.593.511 (5)160

Symmetry codes: (i) ; (ii) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  4 in total

1.  (E)-N'-(3,4-Dimethoxy-benzyl-idene)-2-(8-quinol-yloxy)acetohydrazide-methanol-water (1/1/1).

Authors:  Zhan-Ling Ma
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-28

2.  (E)-N'-(2,5-Dimethoxy-benzyl-idene)-2,4-dihydroxy-benzohydrazide.

Authors:  Jing-Yuan Wei; De-Guang Song; Da-Cheng Wang; Xu-Ming Deng; Ju-Xiong Liu; Bo Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-31

3.  (E)-N'-(3,4,5-Trimethoxy-benzyl-idene)-2-(8-quinol-yloxy)acetohydrazide methanol solvate.

Authors:  Ling Zeng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-04

4.  (E)-N'-(2,5-Dimethoxy-benzyl-idene)-3,4-dihydroxy-benzohydrazide monohydrate.

Authors:  Bin Xu; Ling Han; Qi-Hui Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-03
  4 in total

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