Literature DB >> 22969565

Methyl (E)-3,5-dimeth-oxy-2-{[2-(4-meth-oxy-benzo-yl)hydrazin-1-yl-idene]meth-yl}benzoate.

Humera Naz, Muhammad Taha, Aqilah Abd Rahman, Nor Hadiani Ismail, Sammer Yousuf.   

Abstract

In the title compound, C(19)H(20)N(2)O(6), the azomethine [C=N = 1.269 (2) Å] double bond adopts an E conformation and the dihedral angle between the planes of the benzene rings is 17.41 (11)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(16) loops. The dimers are connected by C-H⋯O and C-H⋯N hydrogen bonds, forming sheets lying parallel to (100).

Entities:  

Year:  2012        PMID： 22969565      PMCID： PMC3435694          DOI： 10.1107/S1600536812034782

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


Related literature

For the biological activity of benzohydraazides, see: Khan et al. (2011 ▶); Chahan et al. (2006 ▶). For a related structure, see: Zhang (2009 ▶).

Experimental

Crystal data

C19H20N2O6 M = 372.37 Triclinic, a = 8.8468 (7) Å b = 10.7392 (8) Å c = 10.9764 (8) Å α = 113.377 (2)° β = 90.656 (2)° γ = 104.695 (2)° V = 918.52 (12) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 298 K 0.28 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.972, T max = 0.989 10426 measured reflections 3415 independent reflections 2224 reflections with I > 2σ(I) R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.114 S = 1.02 3415 reflections 252 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.16 e Å−3 Δρmin = −0.17 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034782/hb6920sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034782/hb6920Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812034782/hb6920Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H20N2O6Z = 2
Mr = 372.37F(000) = 392
Triclinic, P1Dx = 1.346 Mg m−3
a = 8.8468 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7392 (8) ÅCell parameters from 1645 reflections
c = 10.9764 (8) Åθ = 2.0–25.5°
α = 113.377 (2)°µ = 0.10 mm−1
β = 90.656 (2)°T = 298 K
γ = 104.695 (2)°Block, colorless
V = 918.52 (12) Å30.28 × 0.14 × 0.11 mm
Bruker SMART APEX CCD diffractometer3415 independent reflections
Radiation source: fine-focus sealed tube2224 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scanθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −10→10
Tmin = 0.972, Tmax = 0.989k = −13→13
10426 measured reflectionsl = −13→13
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0494P)2 + 0.0289P] where P = (Fo2 + 2Fc2)/3
3415 reflections(Δ/σ)max < 0.001
252 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.17 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
O10.6563 (2)0.64890 (18)1.46257 (16)0.0820 (5)
O20.24378 (19)0.62729 (15)0.97724 (16)0.0730 (5)
O30.17303 (18)1.25061 (14)1.10340 (13)0.0614 (4)
O40.0119 (2)1.17046 (16)0.65074 (14)0.0691 (5)
O50.40868 (17)0.87627 (14)0.73902 (14)0.0564 (4)
O60.16475 (16)0.73913 (14)0.65091 (13)0.0549 (4)
N10.3446 (2)0.86420 (19)1.08462 (18)0.0507 (5)
N20.26850 (18)0.88947 (17)0.98968 (16)0.0477 (4)
C10.4660 (3)0.8228 (2)1.3057 (2)0.0636 (6)
H1B0.44720.90981.32570.076*
C20.5451 (3)0.8037 (2)1.4035 (2)0.0631 (6)
H2B0.57700.87661.48840.076*
C30.5760 (2)0.6779 (2)1.3750 (2)0.0537 (5)
C40.5221 (3)0.5694 (2)1.2506 (2)0.0721 (7)
H4A0.54020.48231.23110.087*
C50.4413 (3)0.5890 (2)1.1549 (2)0.0603 (6)
H5A0.40430.51421.07170.072*
C60.4143 (2)0.7167 (2)1.17971 (19)0.0448 (5)
C70.3274 (2)0.7306 (2)1.0710 (2)0.0488 (5)
C80.2808 (2)1.0184 (2)1.01728 (19)0.0475 (5)
H8A0.33421.08781.09900.057*
C90.2117 (2)1.05887 (19)0.92205 (18)0.0410 (5)
C100.1566 (2)1.17821 (19)0.96804 (18)0.0434 (5)
C110.0895 (2)1.2190 (2)0.88060 (19)0.0491 (5)
H11A0.05541.30010.91290.059*
C120.0739 (2)1.1378 (2)0.74496 (19)0.0480 (5)
C130.1234 (2)1.0168 (2)0.69618 (19)0.0493 (5)
H13A0.10940.96110.60470.059*
C140.1937 (2)0.97907 (19)0.78374 (18)0.0419 (5)
C150.2684 (3)0.8614 (2)0.72612 (18)0.0442 (5)
C160.2293 (3)0.6196 (2)0.5973 (3)0.0761 (7)
H16A0.14610.53530.54700.114*
H16B0.27880.60890.66940.114*
H16C0.30580.63530.53980.114*
C17−0.0109 (3)1.3070 (2)0.6920 (2)0.0695 (7)
H17A−0.03801.32150.61460.104*
H17B0.08441.37750.74200.104*
H17C−0.09451.31420.74710.104*
C180.0967 (3)1.3593 (2)1.1573 (2)0.0617 (6)
H18A0.11471.39881.25320.093*
H18B−0.01451.32031.12820.093*
H18C0.13831.43201.12680.093*
C190.7245 (3)0.7605 (3)1.5882 (3)0.0943 (9)
H19A0.78830.72921.63500.141*
H19B0.64250.78831.64000.141*
H19C0.78880.83961.57500.141*
H1A0.412 (2)0.936 (2)1.141 (2)0.054 (7)*
U11U22U33U12U13U23
O10.1044 (13)0.1002 (13)0.0638 (11)0.0587 (11)−0.0016 (10)0.0388 (10)
O20.0884 (12)0.0517 (9)0.0698 (11)0.0157 (9)−0.0233 (9)0.0191 (8)
O30.0889 (11)0.0613 (9)0.0364 (8)0.0409 (8)−0.0007 (7)0.0109 (7)
O40.1052 (12)0.0728 (10)0.0478 (9)0.0528 (9)0.0012 (8)0.0271 (8)
O50.0507 (9)0.0559 (9)0.0602 (9)0.0234 (7)0.0022 (7)0.0164 (7)
O60.0585 (9)0.0437 (8)0.0583 (9)0.0197 (7)−0.0020 (7)0.0138 (7)
N10.0596 (12)0.0468 (11)0.0467 (11)0.0137 (10)−0.0095 (9)0.0216 (9)
N20.0520 (10)0.0511 (11)0.0444 (10)0.0180 (8)−0.0025 (8)0.0225 (8)
C10.0948 (18)0.0525 (13)0.0532 (14)0.0362 (13)0.0017 (13)0.0225 (11)
C20.0890 (17)0.0623 (15)0.0427 (13)0.0324 (13)0.0019 (12)0.0200 (11)
C30.0572 (13)0.0682 (15)0.0521 (13)0.0309 (12)0.0097 (11)0.0333 (12)
C40.0968 (19)0.0615 (15)0.0710 (17)0.0434 (14)−0.0009 (15)0.0279 (13)
C50.0732 (15)0.0511 (13)0.0551 (14)0.0251 (12)−0.0022 (12)0.0162 (11)
C60.0472 (12)0.0476 (12)0.0461 (12)0.0172 (10)0.0074 (10)0.0235 (10)
C70.0529 (13)0.0457 (13)0.0476 (12)0.0164 (11)0.0014 (10)0.0177 (10)
C80.0559 (13)0.0474 (12)0.0402 (11)0.0182 (10)−0.0031 (9)0.0171 (9)
C90.0432 (11)0.0439 (11)0.0380 (11)0.0144 (9)−0.0002 (9)0.0180 (9)
C100.0508 (12)0.0436 (11)0.0360 (11)0.0180 (10)0.0012 (9)0.0138 (9)
C110.0607 (13)0.0476 (12)0.0467 (12)0.0279 (10)0.0057 (10)0.0197 (10)
C120.0583 (13)0.0541 (13)0.0407 (12)0.0250 (10)0.0026 (10)0.0233 (10)
C130.0610 (13)0.0531 (13)0.0361 (11)0.0259 (11)0.0017 (10)0.0149 (9)
C140.0460 (11)0.0426 (11)0.0410 (11)0.0179 (9)0.0034 (9)0.0178 (9)
C150.0536 (13)0.0476 (12)0.0347 (11)0.0175 (11)0.0005 (10)0.0184 (9)
C160.0824 (17)0.0435 (13)0.0919 (18)0.0268 (12)0.0028 (15)0.0121 (12)
C170.0943 (18)0.0737 (16)0.0675 (16)0.0477 (14)0.0140 (14)0.0416 (13)
C180.0781 (16)0.0566 (14)0.0459 (13)0.0327 (12)0.0067 (11)0.0082 (10)
C190.106 (2)0.133 (3)0.0602 (17)0.065 (2)−0.0023 (16)0.0375 (17)
O1—C31.364 (2)C6—C71.488 (3)
O1—C191.416 (3)C8—C91.461 (2)
O2—C71.224 (2)C8—H8A0.9300
O3—C101.362 (2)C9—C101.394 (2)
O3—C181.425 (2)C9—C141.399 (3)
O4—C121.366 (2)C10—C111.385 (2)
O4—C171.422 (2)C11—C121.378 (3)
O5—C151.209 (2)C11—H11A0.9300
O6—C151.326 (2)C12—C131.382 (3)
O6—C161.450 (2)C13—C141.377 (2)
N1—C71.350 (2)C13—H13A0.9300
N1—N21.383 (2)C14—C151.494 (3)
N1—H1A0.85 (2)C16—H16A0.9600
N2—C81.269 (2)C16—H16B0.9600
C1—C61.375 (3)C16—H16C0.9600
C1—C21.384 (3)C17—H17A0.9600
C1—H1B0.9300C17—H17B0.9600
C2—C31.361 (3)C17—H17C0.9600
C2—H2B0.9300C18—H18A0.9600
C3—C41.375 (3)C18—H18B0.9600
C4—C51.376 (3)C18—H18C0.9600
C4—H4A0.9300C19—H19A0.9600
C5—C61.373 (3)C19—H19B0.9600
C5—H5A0.9300C19—H19C0.9600
C3—O1—C19118.05 (19)C12—C11—H11A120.5
C10—O3—C18118.26 (15)C10—C11—H11A120.5
C12—O4—C17118.22 (16)O4—C12—C11123.46 (18)
C15—O6—C16114.98 (16)O4—C12—C13115.72 (17)
C7—N1—N2120.43 (18)C11—C12—C13120.82 (17)
C7—N1—H1A124.2 (14)C14—C13—C12119.67 (18)
N2—N1—H1A114.6 (14)C14—C13—H13A120.2
C8—N2—N1115.63 (17)C12—C13—H13A120.2
C6—C1—C2121.78 (19)C13—C14—C9121.17 (17)
C6—C1—H1B119.1C13—C14—C15117.78 (17)
C2—C1—H1B119.1C9—C14—C15120.59 (16)
C3—C2—C1119.8 (2)O5—C15—O6123.04 (18)
C3—C2—H2B120.1O5—C15—C14124.35 (18)
C1—C2—H2B120.1O6—C15—C14112.46 (17)
C2—C3—O1124.7 (2)O6—C16—H16A109.5
C2—C3—C4119.3 (2)O6—C16—H16B109.5
O1—C3—C4116.04 (19)H16A—C16—H16B109.5
C3—C4—C5120.3 (2)O6—C16—H16C109.5
C3—C4—H4A119.8H16A—C16—H16C109.5
C5—C4—H4A119.8H16B—C16—H16C109.5
C6—C5—C4121.4 (2)O4—C17—H17A109.5
C6—C5—H5A119.3O4—C17—H17B109.5
C4—C5—H5A119.3H17A—C17—H17B109.5
C5—C6—C1117.35 (19)O4—C17—H17C109.5
C5—C6—C7118.43 (18)H17A—C17—H17C109.5
C1—C6—C7124.20 (18)H17B—C17—H17C109.5
O2—C7—N1122.64 (19)O3—C18—H18A109.5
O2—C7—C6121.79 (18)O3—C18—H18B109.5
N1—C7—C6115.55 (18)H18A—C18—H18B109.5
N2—C8—C9120.71 (18)O3—C18—H18C109.5
N2—C8—H8A119.6H18A—C18—H18C109.5
C9—C8—H8A119.6H18B—C18—H18C109.5
C10—C9—C14117.63 (16)O1—C19—H19A109.5
C10—C9—C8120.10 (17)O1—C19—H19B109.5
C14—C9—C8122.24 (17)H19A—C19—H19B109.5
O3—C10—C11122.77 (17)O1—C19—H19C109.5
O3—C10—C9115.61 (16)H19A—C19—H19C109.5
C11—C10—C9121.61 (17)H19B—C19—H19C109.5
C12—C11—C10119.05 (18)
C7—N1—N2—C8174.00 (18)C14—C9—C10—O3178.40 (17)
C6—C1—C2—C31.2 (4)C8—C9—C10—O30.3 (3)
C1—C2—C3—O1178.3 (2)C14—C9—C10—C11−1.4 (3)
C1—C2—C3—C4−2.7 (3)C8—C9—C10—C11−179.51 (18)
C19—O1—C3—C2−5.8 (3)O3—C10—C11—C12−178.44 (18)
C19—O1—C3—C4175.3 (2)C9—C10—C11—C121.4 (3)
C2—C3—C4—C51.7 (4)C17—O4—C12—C1111.9 (3)
O1—C3—C4—C5−179.3 (2)C17—O4—C12—C13−167.25 (19)
C3—C4—C5—C60.9 (4)C10—C11—C12—O4−178.79 (19)
C4—C5—C6—C1−2.4 (3)C10—C11—C12—C130.4 (3)
C4—C5—C6—C7179.4 (2)O4—C12—C13—C14177.21 (18)
C2—C1—C6—C51.4 (3)C11—C12—C13—C14−2.0 (3)
C2—C1—C6—C7179.4 (2)C12—C13—C14—C91.9 (3)
N2—N1—C7—O2−1.1 (3)C12—C13—C14—C15−170.38 (18)
N2—N1—C7—C6−179.71 (16)C10—C9—C14—C13−0.2 (3)
C5—C6—C7—O220.4 (3)C8—C9—C14—C13177.79 (18)
C1—C6—C7—O2−157.6 (2)C10—C9—C14—C15171.85 (18)
C5—C6—C7—N1−160.94 (19)C8—C9—C14—C15−10.1 (3)
C1—C6—C7—N121.0 (3)C16—O6—C15—O57.0 (3)
N1—N2—C8—C9177.12 (17)C16—O6—C15—C14−177.25 (18)
N2—C8—C9—C10148.9 (2)C13—C14—C15—O5111.9 (2)
N2—C8—C9—C14−29.1 (3)C9—C14—C15—O5−60.4 (3)
C18—O3—C10—C119.9 (3)C13—C14—C15—O6−63.8 (2)
C18—O3—C10—C9−169.98 (18)C9—C14—C15—O6123.87 (19)
D—H···AD—HH···AD···AD—H···A
N1—H1A···O5i0.84 (2)2.13 (2)2.969 (2)172.3 (19)
C18—H18B···N2ii0.962.623.501 (3)153
C19—H19B···O5iii0.962.573.511 (3)168
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1A⋯O5i 0.84 (2)2.13 (2)2.969 (2)172.3 (19)
C18—H18B⋯N2ii 0.962.623.501 (3)153
C19—H19B⋯O5iii 0.962.573.511 (3)168

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

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4.  4-Meth-oxy-N'-(2-methoxy-benzyl-idene)benzohydrazide.

Authors:  Xinyou Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-23

5.  Structure validation in chemical crystallography.

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1.  (E)-2,4-Dimethyl-N'-(2-methyl-benzyl-idene)benzohydrazide.

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