Literature DB >> 21200762

2-Hydr-oxy-N'-[(1Z)-1-(2-hydr-oxy-5-methyl-phen-yl)-2-methyl-propyl-idene]benzohydrazide.

Jian-Guo Chang1, Ren-Gao Zhao.   

Abstract

The title compound, C(18)H(20)N(2)O(3), adopts a cis conformation with respect to the C=N double bond. The crystal structure is stabilized by intra-molecular N-H⋯O and inter-molecular O-H⋯O hydrogen bonds.

Entities:  

Year:  2007        PMID： 21200762      PMCID： PMC2915260          DOI： 10.1107/S160053680706357X

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


Related literature

For further details of the chemistry of the title compound, see: Carcelli et al. (1995 ▶); Salem (1998 ▶).

Experimental

Crystal data

C18H20N2O3 M = 312.36 Monoclinic, a = 11.2144 (11) Å b = 11.2887 (11) Å c = 13.6535 (13) Å β = 107.000 (2)° V = 1653.0 (3) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 273 (2) K 0.25 × 0.22 × 0.16 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.987, T max = 0.991 8523 measured reflections 2924 independent reflections 2094 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.139 S = 1.00 2924 reflections 210 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.15 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706357X/pk2070sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680706357X/pk2070Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H20N2O3F000 = 664
Mr = 312.36Dx = 1.255 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2019 reflections
a = 11.2144 (11) Åθ = 2.6–23.2º
b = 11.2887 (11) ŵ = 0.09 mm−1
c = 13.6535 (13) ÅT = 273 (2) K
β = 107.000 (2)ºBlock, yellow
V = 1653.0 (3) Å30.25 × 0.22 × 0.16 mm
Z = 4
Bruker APEX2 CCD area-detector diffractometer2924 independent reflections
Radiation source: fine-focus sealed tube2094 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 273(2) Kθmax = 25.1º
φ and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −13→10
Tmin = 0.987, Tmax = 0.991k = −12→13
8523 measured reflectionsl = −10→16
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.0879P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2924 reflectionsΔρmax = 0.20 e Å−3
210 parametersΔρmin = −0.15 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
O10.14313 (13)0.32510 (11)0.31013 (11)0.0609 (4)
H10.15000.39650.32150.091*
O20.01561 (11)0.20180 (13)−0.04931 (10)0.0629 (4)
H20.04610.2149−0.09600.094*
O3−0.20731 (11)0.03822 (11)0.10448 (9)0.0555 (4)
N1−0.01360 (13)0.10594 (12)0.11865 (10)0.0445 (4)
H1A0.03460.14420.09100.053*
N20.03470 (14)0.05414 (12)0.21453 (11)0.0444 (4)
C10.21322 (16)0.29390 (14)0.24792 (13)0.0426 (4)
C20.21798 (15)0.17485 (15)0.22370 (12)0.0397 (4)
C30.28605 (16)0.14187 (17)0.15787 (14)0.0496 (5)
H30.28920.06230.14120.060*
C40.34956 (16)0.22417 (19)0.11622 (14)0.0546 (5)
C50.34352 (18)0.34066 (19)0.14234 (14)0.0566 (5)
H50.38570.39720.11560.068*
C60.27685 (18)0.37622 (17)0.20703 (14)0.0553 (5)
H60.27440.45600.22350.066*
C70.4215 (2)0.1856 (2)0.04319 (17)0.0788 (7)
H7A0.47350.24950.03370.118*
H7B0.36400.1644−0.02160.118*
H7C0.47250.11840.07130.118*
C80.14484 (16)0.08723 (14)0.26466 (13)0.0416 (4)
C90.20075 (18)0.03997 (16)0.37216 (14)0.0538 (5)
H90.21790.10890.41780.065*
C100.1119 (2)−0.0383 (2)0.40763 (17)0.0856 (8)
H10A0.03600.00420.40180.128*
H10B0.1495−0.06050.47770.128*
H10C0.0938−0.10810.36580.128*
C110.3253 (2)−0.0202 (2)0.38364 (17)0.0832 (7)
H11A0.3138−0.08530.33660.125*
H11B0.3584−0.04900.45240.125*
H11C0.38240.03570.36920.125*
C12−0.13535 (15)0.09610 (14)0.06947 (13)0.0399 (4)
C13−0.18372 (15)0.16196 (14)−0.02863 (12)0.0394 (4)
C14−0.11049 (17)0.21255 (15)−0.08482 (13)0.0443 (4)
C15−0.1663 (2)0.27366 (17)−0.17470 (15)0.0580 (5)
H15−0.11750.3059−0.21250.070*
C16−0.2935 (2)0.28657 (18)−0.20782 (16)0.0655 (6)
H16−0.33010.3283−0.26780.079*
C17−0.3677 (2)0.23870 (19)−0.15361 (16)0.0633 (6)
H17−0.45380.2483−0.17620.076*
C18−0.31253 (17)0.17651 (16)−0.06546 (15)0.0522 (5)
H18−0.36270.1431−0.02930.063*
U11U22U33U12U13U23
O10.0832 (10)0.0437 (7)0.0734 (9)0.0020 (7)0.0506 (8)−0.0056 (7)
O20.0526 (8)0.0929 (11)0.0496 (8)−0.0065 (7)0.0248 (7)0.0118 (7)
O30.0500 (8)0.0617 (8)0.0590 (8)−0.0089 (6)0.0224 (7)0.0137 (6)
N10.0446 (8)0.0515 (9)0.0388 (8)−0.0079 (6)0.0144 (7)0.0083 (7)
N20.0531 (9)0.0425 (8)0.0390 (8)−0.0005 (7)0.0159 (7)0.0044 (6)
C10.0462 (10)0.0433 (10)0.0424 (10)0.0036 (8)0.0193 (8)−0.0023 (8)
C20.0377 (9)0.0448 (10)0.0356 (9)0.0011 (7)0.0091 (7)−0.0026 (7)
C30.0451 (10)0.0563 (11)0.0489 (11)−0.0003 (8)0.0159 (9)−0.0156 (9)
C40.0395 (10)0.0822 (15)0.0439 (11)−0.0058 (9)0.0150 (9)−0.0101 (10)
C50.0545 (12)0.0673 (13)0.0523 (12)−0.0135 (10)0.0222 (10)0.0019 (10)
C60.0665 (13)0.0441 (10)0.0600 (12)−0.0056 (9)0.0258 (10)−0.0020 (9)
C70.0599 (13)0.119 (2)0.0680 (15)−0.0099 (12)0.0356 (12)−0.0210 (13)
C80.0488 (10)0.0365 (9)0.0405 (10)0.0040 (8)0.0145 (8)−0.0015 (8)
C90.0671 (13)0.0478 (11)0.0421 (11)0.0050 (9)0.0090 (9)0.0029 (8)
C100.103 (2)0.0882 (18)0.0617 (14)−0.0075 (14)0.0178 (14)0.0322 (13)
C110.0838 (17)0.0863 (17)0.0682 (15)0.0305 (13)0.0047 (13)0.0085 (13)
C120.0441 (10)0.0372 (9)0.0424 (10)−0.0035 (7)0.0189 (8)−0.0023 (7)
C130.0462 (10)0.0373 (9)0.0374 (9)−0.0018 (7)0.0161 (8)−0.0043 (7)
C140.0482 (10)0.0467 (10)0.0395 (10)−0.0063 (8)0.0154 (8)−0.0023 (8)
C150.0756 (15)0.0597 (12)0.0397 (11)−0.0133 (10)0.0185 (10)0.0026 (9)
C160.0818 (16)0.0580 (13)0.0460 (12)−0.0033 (11)0.0021 (11)0.0042 (9)
C170.0544 (12)0.0653 (13)0.0603 (13)0.0054 (10)0.0012 (10)−0.0001 (11)
C180.0468 (11)0.0572 (11)0.0542 (12)−0.0003 (9)0.0172 (9)−0.0044 (10)
O1—C11.3615 (19)C7—H7C0.9600
O1—H10.8200C8—C91.515 (2)
O2—C141.360 (2)C9—C101.513 (3)
O2—H20.8200C9—C111.519 (3)
O3—C121.2377 (19)C9—H90.9800
N1—C121.338 (2)C10—H10A0.9600
N1—N21.3909 (19)C10—H10B0.9600
N1—H1A0.8600C10—H10C0.9600
N2—C81.280 (2)C11—H11A0.9600
C1—C61.385 (2)C11—H11B0.9600
C1—C21.389 (2)C11—H11C0.9600
C2—C31.389 (2)C12—C131.489 (2)
C2—C81.494 (2)C13—C181.393 (2)
C3—C41.389 (3)C13—C141.399 (2)
C3—H30.9300C14—C151.387 (3)
C4—C51.369 (3)C15—C161.372 (3)
C4—C71.518 (2)C15—H150.9300
C5—C61.373 (3)C16—C171.376 (3)
C5—H50.9300C16—H160.9300
C6—H60.9300C17—C181.374 (3)
C7—H7A0.9600C17—H170.9300
C7—H7B0.9600C18—H180.9300
C1—O1—H1109.5C10—C9—H9106.6
C14—O2—H2109.5C8—C9—H9106.6
C12—N1—N2119.78 (13)C11—C9—H9106.6
C12—N1—H1A120.1C9—C10—H10A109.5
N2—N1—H1A120.1C9—C10—H10B109.5
C8—N2—N1115.46 (14)H10A—C10—H10B109.5
O1—C1—C6122.51 (15)C9—C10—H10C109.5
O1—C1—C2117.92 (15)H10A—C10—H10C109.5
C6—C1—C2119.56 (16)H10B—C10—H10C109.5
C1—C2—C3118.68 (16)C9—C11—H11A109.5
C1—C2—C8119.21 (14)C9—C11—H11B109.5
C3—C2—C8122.03 (15)H11A—C11—H11B109.5
C2—C3—C4122.00 (18)C9—C11—H11C109.5
C2—C3—H3119.0H11A—C11—H11C109.5
C4—C3—H3119.0H11B—C11—H11C109.5
C5—C4—C3117.72 (16)O3—C12—N1122.33 (15)
C5—C4—C7121.53 (18)O3—C12—C13120.26 (15)
C3—C4—C7120.74 (19)N1—C12—C13117.38 (13)
C4—C5—C6121.73 (17)C18—C13—C14117.82 (16)
C4—C5—H5119.1C18—C13—C12116.76 (14)
C6—C5—H5119.1C14—C13—C12125.40 (15)
C5—C6—C1120.31 (18)O2—C14—C15120.87 (16)
C5—C6—H6119.8O2—C14—C13118.95 (15)
C1—C6—H6119.8C15—C14—C13120.18 (17)
C4—C7—H7A109.5C16—C15—C14120.07 (18)
C4—C7—H7B109.5C16—C15—H15120.0
H7A—C7—H7B109.5C14—C15—H15120.0
C4—C7—H7C109.5C15—C16—C17121.00 (19)
H7A—C7—H7C109.5C15—C16—H16119.5
H7B—C7—H7C109.5C17—C16—H16119.5
N2—C8—C2122.85 (15)C18—C17—C16118.89 (19)
N2—C8—C9118.46 (15)C18—C17—H17120.6
C2—C8—C9118.62 (15)C16—C17—H17120.6
C10—C9—C8113.01 (17)C17—C18—C13122.03 (18)
C10—C9—C11112.20 (18)C17—C18—H18119.0
C8—C9—C11111.40 (16)C13—C18—H18119.0
C12—N1—N2—C8−166.53 (15)C2—C8—C9—C10174.27 (17)
O1—C1—C2—C3178.11 (16)N2—C8—C9—C11124.62 (19)
C6—C1—C2—C3−0.6 (3)C2—C8—C9—C11−58.3 (2)
O1—C1—C2—C81.2 (2)N2—N1—C12—O3−2.8 (2)
C6—C1—C2—C8−177.50 (16)N2—N1—C12—C13174.85 (14)
C1—C2—C3—C40.3 (3)O3—C12—C13—C1813.7 (2)
C8—C2—C3—C4177.10 (16)N1—C12—C13—C18−163.97 (15)
C2—C3—C4—C50.2 (3)O3—C12—C13—C14−168.03 (16)
C2—C3—C4—C7−179.04 (17)N1—C12—C13—C1414.3 (2)
C3—C4—C5—C6−0.3 (3)C18—C13—C14—O2178.59 (16)
C7—C4—C5—C6178.90 (19)C12—C13—C14—O20.4 (2)
C4—C5—C6—C10.0 (3)C18—C13—C14—C15−0.7 (2)
O1—C1—C6—C5−178.17 (18)C12—C13—C14—C15−178.97 (16)
C2—C1—C6—C50.5 (3)O2—C14—C15—C16−178.11 (17)
N1—N2—C8—C2−0.4 (2)C13—C14—C15—C161.2 (3)
N1—N2—C8—C9176.55 (14)C14—C15—C16—C17−0.6 (3)
C1—C2—C8—N293.6 (2)C15—C16—C17—C18−0.5 (3)
C3—C2—C8—N2−83.1 (2)C16—C17—C18—C130.9 (3)
C1—C2—C8—C9−83.3 (2)C14—C13—C18—C17−0.3 (3)
C3—C2—C8—C999.94 (19)C12—C13—C18—C17178.06 (17)
N2—C8—C9—C10−2.8 (3)
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.861.982.6413 (18)133
O2—H2···O1i0.821.962.7249 (17)155
O1—H1···O3ii0.821.902.6787 (18)158
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯O20.861.982.6413 (18)133
O2—H2⋯O1i0.821.962.7249 (17)155
O1—H1⋯O3ii0.821.902.6787 (18)158

Symmetry codes: (i) ; (ii) .

  1 in total

1.  Antimicrobial and genotoxic activity of 2,6-diacetylpyridine bis(acylhydrazones) and their complexes with some first transition series metal ions. X-ray crystal structure of a dinuclear copper(II) complex.

Authors:  M Carcelli; P Mazza; C Pelizzi; G Pelizzi; F Zani
Journal:  J Inorg Biochem       Date:  1995-01       Impact factor: 4.155
  1 in total

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