Literature DB >> 21754475

1-(2,3-Dimeth-oxy-benzyl-idene)-2-(2,4-dinitro-phen-yl)hydrazine.

Xianrong Xin, Min Li, Zhimin Chen, Ruitao Zhu.   

Abstract

In the title compound, C(15)H(14)N(4)O(6), the dihedral angle between the aromatic rings is 3.7 (4)°. The n class="Chemical">nitro groups make dihedral angles of 6.0 (4) and 5.2 (4)° with the parent ring and are oriented at 6.0 (6)° with respect to each other. The meth-oxy groups are inclined at 54.0 (2) and 2.5 (3)° with respect to the benzene ring to which they are attached. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions. The mol-ecular conformation is consolidated by an intra-molecular N-H⋯O hydrogen bond.

Entities:  

Year:  2011        PMID： 21754475      PMCID： PMC3089222          DOI： 10.1107/S1600536811013894

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


Related literature

For general background to the properties of Schiff base compounds, see: Mufakkar et al. (2010 ▶); Tahir et al. (2010 ▶). For related structures, see: Salhin et al. (2007 ▶); Tameem et al. (2008 ▶); Shao et al. (2008 ▶).

Experimental

Crystal data

C15H14N4O6 M = 346.30 Triclinic, a = 7.8409 (8) Å b = 7.9200 (9) Å c = 13.8961 (14) Å α = 85.038 (2)° β = 82.773 (1)° γ = 65.894 (1)° V = 780.85 (14) Å3 Z = 2 Mo Kα radiation μ = 0.12 mm−1 T = 298 K 0.43 × 0.38 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.952, T max = 0.958 4130 measured reflections 2725 independent reflections 1414 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.063 wR(F 2) = 0.178 S = 1.06 2725 reflections 229 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.25 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013894/pv2405sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013894/pv2405Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H14N4O6Z = 2
Mr = 346.30F(000) = 360
Triclinic, P1Dx = 1.473 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8409 (8) ÅCell parameters from 855 reflections
b = 7.9200 (9) Åθ = 2.8–22.8°
c = 13.8961 (14) ŵ = 0.12 mm−1
α = 85.038 (2)°T = 298 K
β = 82.773 (1)°Block, orange
γ = 65.894 (1)°0.43 × 0.38 × 0.37 mm
V = 780.85 (14) Å3
Bruker SMART CCD diffractometer2725 independent reflections
Radiation source: fine-focus sealed tube1414 reflections with I > 2σ(I)
graphiteRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −9→9
Tmin = 0.952, Tmax = 0.958k = −9→9
4130 measured reflectionsl = −16→8
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.178w = 1/[σ2(Fo2) + (0.0737P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2725 reflectionsΔρmax = 0.28 e Å−3
229 parametersΔρmin = −0.25 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (5)
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
N10.6288 (3)0.1887 (3)0.55122 (17)0.0672 (7)
H10.72900.19950.52430.081*
N20.4685 (3)0.2598 (3)0.50406 (17)0.0627 (6)
N30.9691 (3)0.0341 (4)0.6504 (3)0.0789 (8)
N40.6248 (5)−0.1660 (4)0.9164 (2)0.0889 (9)
O10.9777 (3)0.1238 (4)0.57412 (19)0.0936 (8)
O21.1061 (3)−0.0474 (4)0.6963 (2)0.1191 (10)
O30.7741 (4)−0.2406 (4)0.9539 (2)0.1259 (11)
O40.4763 (4)−0.1674 (4)0.95499 (18)0.1107 (9)
O50.5156 (3)0.5336 (3)0.25258 (14)0.0734 (6)
O60.2347 (3)0.6845 (3)0.13346 (16)0.0810 (7)
C10.6302 (3)0.1025 (3)0.6391 (2)0.0549 (7)
C20.7926 (3)0.0256 (4)0.6903 (2)0.0626 (8)
C30.7883 (4)−0.0608 (4)0.7802 (2)0.0681 (8)
H30.8956−0.10940.81300.082*
C40.6287 (4)−0.0754 (4)0.8214 (2)0.0652 (8)
C50.4661 (4)−0.0033 (4)0.7723 (2)0.0651 (8)
H50.3567−0.01360.80080.078*
C60.4688 (4)0.0809 (4)0.6841 (2)0.0609 (7)
H60.36090.12600.65180.073*
C70.4850 (4)0.3361 (4)0.4206 (2)0.0627 (7)
H70.60000.33940.39680.075*
C80.3275 (4)0.4181 (4)0.3620 (2)0.0588 (7)
C90.3505 (4)0.5101 (4)0.2741 (2)0.0602 (7)
C100.2012 (4)0.5909 (4)0.2156 (2)0.0641 (8)
C110.0346 (4)0.5735 (4)0.2461 (2)0.0744 (9)
H11−0.06430.62400.20740.089*
C120.0117 (4)0.4825 (4)0.3330 (3)0.0756 (9)
H12−0.10260.47400.35250.091*
C130.1564 (4)0.4046 (4)0.3907 (2)0.0684 (8)
H130.14040.34280.44880.082*
C140.6191 (4)0.4797 (5)0.1608 (2)0.0847 (10)
H14A0.57710.39910.13230.127*
H14B0.75030.41590.16910.127*
H14C0.59980.58770.11900.127*
C150.0951 (5)0.7525 (5)0.0675 (3)0.1016 (12)
H15A0.07180.65160.04720.152*
H15B0.13780.81070.01180.152*
H15C−0.01870.84120.09870.152*
U11U22U33U12U13U23
N10.0509 (13)0.0903 (17)0.0649 (17)−0.0324 (12)−0.0047 (11)−0.0079 (13)
N20.0547 (14)0.0696 (15)0.0639 (16)−0.0245 (12)−0.0081 (11)−0.0030 (12)
N30.0472 (15)0.0818 (19)0.110 (2)−0.0237 (14)−0.0100 (15)−0.0246 (16)
N40.117 (3)0.088 (2)0.081 (2)−0.0550 (19)−0.0386 (19)0.0088 (16)
O10.0661 (14)0.133 (2)0.0922 (18)−0.0513 (14)0.0068 (12)−0.0250 (15)
O20.0526 (13)0.124 (2)0.180 (3)−0.0300 (13)−0.0379 (16)0.0068 (18)
O30.136 (2)0.138 (2)0.114 (2)−0.0557 (18)−0.0725 (19)0.0353 (17)
O40.142 (2)0.140 (2)0.0873 (19)−0.095 (2)−0.0317 (16)0.0251 (15)
O50.0724 (13)0.0967 (15)0.0642 (13)−0.0473 (12)−0.0049 (10)−0.0064 (10)
O60.0827 (14)0.0920 (15)0.0730 (15)−0.0389 (12)−0.0219 (11)0.0126 (12)
C10.0492 (15)0.0540 (15)0.0625 (19)−0.0194 (13)−0.0076 (12)−0.0111 (13)
C20.0461 (16)0.0640 (18)0.080 (2)−0.0201 (13)−0.0103 (14)−0.0183 (16)
C30.0621 (19)0.0584 (17)0.087 (2)−0.0196 (15)−0.0281 (16)−0.0119 (16)
C40.077 (2)0.0615 (17)0.066 (2)−0.0324 (15)−0.0250 (15)−0.0003 (14)
C50.0628 (18)0.0648 (18)0.076 (2)−0.0329 (15)−0.0142 (15)0.0020 (15)
C60.0515 (16)0.0651 (17)0.070 (2)−0.0256 (13)−0.0144 (13)−0.0007 (15)
C70.0573 (17)0.0741 (19)0.0600 (19)−0.0302 (15)−0.0019 (13)−0.0060 (15)
C80.0543 (16)0.0630 (17)0.0602 (18)−0.0240 (14)−0.0005 (13)−0.0129 (13)
C90.0572 (17)0.0653 (17)0.0628 (19)−0.0287 (14)−0.0009 (13)−0.0125 (14)
C100.0627 (18)0.0639 (18)0.067 (2)−0.0250 (15)−0.0085 (14)−0.0074 (15)
C110.0620 (19)0.075 (2)0.089 (2)−0.0260 (16)−0.0185 (16)−0.0074 (17)
C120.0578 (18)0.078 (2)0.095 (3)−0.0327 (16)0.0006 (17)−0.0115 (18)
C130.0627 (18)0.0689 (19)0.076 (2)−0.0293 (15)−0.0014 (15)−0.0098 (15)
C140.080 (2)0.113 (3)0.072 (2)−0.051 (2)−0.0011 (16)−0.0033 (18)
C150.095 (3)0.120 (3)0.084 (3)−0.035 (2)−0.032 (2)0.019 (2)
N1—C11.345 (3)C5—C61.347 (4)
N1—N21.375 (3)C5—H50.9300
N1—H10.8600C6—H60.9300
N2—C71.278 (3)C7—C81.455 (4)
N3—O21.230 (3)C7—H70.9300
N3—O11.234 (3)C8—C131.395 (4)
N3—C21.451 (4)C8—C91.397 (4)
N4—O41.223 (3)C9—C101.408 (4)
N4—O31.236 (3)C10—C111.379 (4)
N4—C41.450 (4)C11—C121.382 (4)
O5—C91.375 (3)C11—H110.9300
O5—C141.420 (3)C12—C131.372 (4)
O6—C101.363 (3)C12—H120.9300
O6—C151.420 (3)C13—H130.9300
C1—C61.407 (4)C14—H14A0.9600
C1—C21.421 (4)C14—H14B0.9600
C2—C31.375 (4)C14—H14C0.9600
C3—C41.355 (4)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.404 (4)C15—H15C0.9600
C1—N1—N2120.6 (2)C8—C7—H7119.4
C1—N1—H1119.7C13—C8—C9119.6 (3)
N2—N1—H1119.7C13—C8—C7121.7 (3)
C7—N2—N1114.9 (2)C9—C8—C7118.7 (2)
O2—N3—O1122.2 (3)O5—C9—C8117.6 (2)
O2—N3—C2117.5 (3)O5—C9—C10121.8 (3)
O1—N3—C2120.3 (3)C8—C9—C10120.2 (3)
O4—N4—O3123.2 (3)O6—C10—C11125.7 (3)
O4—N4—C4119.1 (3)O6—C10—C9115.8 (3)
O3—N4—C4117.7 (3)C11—C10—C9118.4 (3)
C9—O5—C14118.8 (2)C10—C11—C12121.4 (3)
C10—O6—C15117.7 (2)C10—C11—H11119.3
N1—C1—C6120.8 (2)C12—C11—H11119.3
N1—C1—C2122.6 (3)C13—C12—C11120.4 (3)
C6—C1—C2116.5 (3)C13—C12—H12119.8
C3—C2—C1121.0 (3)C11—C12—H12119.8
C3—C2—N3117.3 (3)C12—C13—C8120.0 (3)
C1—C2—N3121.8 (3)C12—C13—H13120.0
C4—C3—C2120.4 (3)C8—C13—H13120.0
C4—C3—H3119.8O5—C14—H14A109.5
C2—C3—H3119.8O5—C14—H14B109.5
C3—C4—C5120.2 (3)H14A—C14—H14B109.5
C3—C4—N4120.1 (3)O5—C14—H14C109.5
C5—C4—N4119.6 (3)H14A—C14—H14C109.5
C6—C5—C4119.9 (3)H14B—C14—H14C109.5
C6—C5—H5120.0O6—C15—H15A109.5
C4—C5—H5120.0O6—C15—H15B109.5
C5—C6—C1121.9 (2)H15A—C15—H15B109.5
C5—C6—H6119.0O6—C15—H15C109.5
C1—C6—H6119.0H15A—C15—H15C109.5
N2—C7—C8121.3 (3)H15B—C15—H15C109.5
N2—C7—H7119.4
C1—N1—N2—C7−179.1 (2)C2—C1—C6—C52.0 (4)
N2—N1—C1—C60.9 (4)N1—N2—C7—C8−179.8 (2)
N2—N1—C1—C2179.5 (2)N2—C7—C8—C13−5.0 (4)
N1—C1—C2—C3179.7 (2)N2—C7—C8—C9175.9 (2)
C6—C1—C2—C3−1.7 (4)C14—O5—C9—C8129.0 (3)
N1—C1—C2—N3−0.4 (4)C14—O5—C9—C10−57.3 (4)
C6—C1—C2—N3178.2 (2)C13—C8—C9—O5174.7 (2)
O2—N3—C2—C34.9 (4)C7—C8—C9—O5−6.3 (4)
O1—N3—C2—C3−173.6 (3)C13—C8—C9—C100.9 (4)
O2—N3—C2—C1−174.9 (3)C7—C8—C9—C10180.0 (2)
O1—N3—C2—C16.6 (4)C15—O6—C10—C11−7.7 (4)
C1—C2—C3—C40.6 (4)C15—O6—C10—C9173.9 (3)
N3—C2—C3—C4−179.3 (2)O5—C9—C10—O63.7 (4)
C2—C3—C4—C50.3 (4)C8—C9—C10—O6177.2 (2)
C2—C3—C4—N4−179.8 (2)O5—C9—C10—C11−174.8 (2)
O4—N4—C4—C3175.4 (3)C8—C9—C10—C11−1.4 (4)
O3—N4—C4—C3−5.5 (4)O6—C10—C11—C12−177.0 (3)
O4—N4—C4—C5−4.7 (4)C9—C10—C11—C121.3 (4)
O3—N4—C4—C5174.4 (3)C10—C11—C12—C13−0.9 (5)
C3—C4—C5—C60.0 (4)C11—C12—C13—C80.4 (5)
N4—C4—C5—C6−179.9 (2)C9—C8—C13—C12−0.5 (4)
C4—C5—C6—C1−1.2 (4)C7—C8—C13—C12−179.5 (3)
N1—C1—C6—C5−179.3 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.992.625 (4)130
N1—H1···N30.862.602.913 (4)103
C3—H3···O20.932.332.654 (4)100
C6—H6···N20.932.442.766 (4)100
C7—H7···O50.932.412.737 (4)101
C14—H14A···O4i0.962.483.431 (4)170
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O10.861.992.625 (4)130
C14—H14A⋯O4i0.962.483.431 (4)170

Symmetry code: (i) .

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