Literature DB >> 21580041

(2E)-N'-Benzoyl-3-(4-nitro-phen-yl)prop-2-enohydrazide.

Samir A Carvalho, Edson F da Silva, Marcus V N de Souza, Edward R T Tiekink, James L Wardell, Solange M S V Wardell.   

Abstract

In the title compound, C(16)H(13)N(3)O(4), the dihedral angle between the terminal n class="Chemical">benzene rings is 14.02 (7)°. The carbonyl groups are anti with respect to each other, which facilitates their participation in the formation of supra-molecular chains. Each side of the -C(=O)N(H)N(H)C(=O)- residue associates with a centrosymmetrically related mol-ecule, resulting in the formation of essentially flat ten-membered {⋯O=CNN(H)}(2) synthons. The resultant chains are further consolidated in the crystal structure via C-H⋯O contacts.

Entities:  

Year:  2009        PMID： 21580041      PMCID： PMC2980068          DOI： 10.1107/S1600536809053379

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


Related literature

For background to the biological activity of trans-cinnamic acid derivatives, see: Bezerra et al. (2006 ▶); Chung & Shin (2007 ▶); Naz et al. (2006 ▶). For background to the development of n class="Chemical">hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C16H13N3O4 M = 311.29 Triclinic, a = 6.8263 (2) Å b = 9.6483 (3) Å c = 10.8571 (3) Å α = 95.535 (2)° β = 102.701 (2)° γ = 91.728 (2)° V = 693.35 (4) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 120 K 0.50 × 0.40 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.664, T max = 0.746 15199 measured reflections 3157 independent reflections 2495 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.127 S = 1.06 3157 reflections 214 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.31 e Å−3 Δρmin = −0.31 e Å−3 Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053379/hb5278sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053379/hb5278Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13N3O4Z = 2
Mr = 311.29F(000) = 324
Triclinic, P1Dx = 1.491 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8263 (2) ÅCell parameters from 7821 reflections
b = 9.6483 (3) Åθ = 2.9–27.5°
c = 10.8571 (3) ŵ = 0.11 mm−1
α = 95.535 (2)°T = 120 K
β = 102.701 (2)°Block, orange
γ = 91.728 (2)°0.50 × 0.40 × 0.20 mm
V = 693.35 (4) Å3
Nonius KappaCCD diffractometer3157 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode2495 reflections with I > 2σ(I)
10 cm confocal mirrorsRint = 0.047
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
φ and ω scansh = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)k = −12→12
Tmin = 0.664, Tmax = 0.746l = −14→13
15199 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0687P)2 + 0.1871P] where P = (Fo2 + 2Fc2)/3
3157 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 0.31 e Å−3
2 restraintsΔρmin = −0.31 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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
O1−0.61174 (17)0.25925 (13)1.01283 (12)0.0338 (3)
O2−0.39300 (16)0.42685 (11)1.10137 (10)0.0231 (3)
O30.30141 (14)0.06073 (10)0.52732 (10)0.0185 (2)
O40.68693 (15)0.44415 (10)0.44917 (10)0.0214 (3)
N1−0.45702 (18)0.33067 (13)1.01817 (12)0.0203 (3)
N20.44535 (17)0.27625 (12)0.53463 (11)0.0154 (3)
H2N0.444 (2)0.3677 (10)0.5437 (15)0.018*
N30.56991 (17)0.22492 (12)0.45712 (11)0.0155 (3)
H3N0.585 (2)0.1348 (10)0.4560 (15)0.019*
C1−0.1035 (2)0.22612 (15)0.75127 (13)0.0150 (3)
C2−0.2558 (2)0.13309 (15)0.76568 (13)0.0180 (3)
H2−0.27770.04480.71660.022*
C3−0.3753 (2)0.16829 (16)0.85096 (14)0.0204 (3)
H3−0.47840.10480.86100.024*
C4−0.3414 (2)0.29731 (15)0.92086 (13)0.0169 (3)
C5−0.1974 (2)0.39458 (15)0.90566 (14)0.0191 (3)
H5−0.18080.48430.95230.023*
C6−0.0783 (2)0.35802 (15)0.82096 (14)0.0194 (3)
H60.02190.42320.80990.023*
C70.0287 (2)0.17919 (14)0.66696 (13)0.0153 (3)
H70.00280.08690.62580.018*
C80.1816 (2)0.25341 (14)0.64252 (13)0.0160 (3)
H80.20780.34840.67640.019*
C90.3096 (2)0.18722 (14)0.56259 (13)0.0142 (3)
C100.6883 (2)0.31779 (14)0.41785 (13)0.0149 (3)
C110.8125 (2)0.25900 (14)0.33038 (13)0.0151 (3)
C120.9921 (2)0.33116 (15)0.32771 (14)0.0180 (3)
H121.03780.41220.38500.022*
C131.1038 (2)0.28350 (16)0.24048 (15)0.0220 (3)
H131.22700.33120.23930.026*
C141.0350 (2)0.16644 (16)0.15541 (15)0.0241 (3)
H141.10970.13580.09460.029*
C150.8579 (2)0.09389 (16)0.15851 (15)0.0248 (3)
H150.81250.01300.10100.030*
C160.7471 (2)0.14018 (15)0.24624 (14)0.0197 (3)
H160.62610.09040.24870.024*
U11U22U33U12U13U23
O10.0268 (6)0.0377 (7)0.0412 (7)−0.0068 (5)0.0216 (5)−0.0036 (6)
O20.0277 (6)0.0234 (6)0.0190 (5)0.0054 (4)0.0076 (4)−0.0003 (4)
O30.0205 (5)0.0113 (5)0.0255 (5)0.0010 (4)0.0099 (4)0.0008 (4)
O40.0240 (5)0.0109 (5)0.0323 (6)0.0005 (4)0.0144 (5)−0.0002 (4)
N10.0190 (6)0.0233 (7)0.0209 (6)0.0034 (5)0.0092 (5)0.0024 (5)
N20.0185 (6)0.0106 (6)0.0209 (6)0.0027 (5)0.0125 (5)0.0007 (5)
N30.0173 (6)0.0114 (6)0.0208 (6)0.0021 (5)0.0111 (5)0.0007 (5)
C10.0144 (6)0.0171 (7)0.0145 (6)0.0026 (5)0.0040 (5)0.0032 (5)
C20.0181 (7)0.0159 (7)0.0198 (7)−0.0014 (5)0.0059 (6)−0.0013 (5)
C30.0169 (7)0.0218 (7)0.0239 (7)−0.0040 (6)0.0090 (6)0.0005 (6)
C40.0147 (7)0.0207 (7)0.0169 (7)0.0028 (5)0.0069 (5)0.0013 (6)
C50.0212 (7)0.0151 (7)0.0219 (7)0.0009 (6)0.0079 (6)−0.0012 (6)
C60.0192 (7)0.0166 (7)0.0250 (7)−0.0014 (5)0.0107 (6)0.0020 (6)
C70.0156 (7)0.0149 (7)0.0156 (7)0.0021 (5)0.0042 (5)0.0013 (5)
C80.0182 (7)0.0127 (7)0.0185 (7)0.0031 (5)0.0069 (5)0.0010 (5)
C90.0133 (6)0.0142 (7)0.0154 (6)0.0008 (5)0.0037 (5)0.0023 (5)
C100.0148 (6)0.0131 (7)0.0173 (7)0.0008 (5)0.0046 (5)0.0019 (5)
C110.0174 (7)0.0139 (7)0.0168 (6)0.0039 (5)0.0077 (5)0.0048 (5)
C120.0176 (7)0.0166 (7)0.0210 (7)0.0011 (5)0.0059 (6)0.0034 (6)
C130.0185 (7)0.0237 (8)0.0282 (8)0.0039 (6)0.0119 (6)0.0088 (6)
C140.0312 (8)0.0234 (8)0.0244 (8)0.0090 (6)0.0182 (7)0.0063 (6)
C150.0373 (9)0.0172 (7)0.0228 (7)0.0019 (6)0.0133 (7)0.0003 (6)
C160.0232 (7)0.0159 (7)0.0223 (7)−0.0008 (6)0.0104 (6)0.0022 (6)
O1—N11.2309 (16)C5—H50.9500
O2—N11.2282 (16)C6—H60.9500
O3—C91.2392 (16)C7—C81.3360 (19)
O4—C101.2346 (16)C7—H70.9500
N1—C41.4695 (17)C8—C91.4784 (18)
N2—C91.3469 (17)C8—H80.9500
N2—N31.3914 (16)C10—C111.4905 (18)
N2—H2N0.879 (9)C11—C161.3913 (19)
N3—C101.3490 (18)C11—C121.399 (2)
N3—H3N0.878 (9)C12—C131.394 (2)
C1—C21.3974 (19)C12—H120.9500
C1—C61.402 (2)C13—C141.388 (2)
C1—C71.4717 (18)C13—H130.9500
C2—C31.3884 (19)C14—C151.387 (2)
C2—H20.9500C14—H140.9500
C3—C41.379 (2)C15—C161.391 (2)
C3—H30.9500C15—H150.9500
C4—C51.386 (2)C16—H160.9500
C5—C61.3834 (19)
O2—N1—O1123.49 (12)C1—C7—H7116.8
O2—N1—C4118.41 (11)C7—C8—C9119.74 (13)
O1—N1—C4118.09 (12)C7—C8—H8120.1
C9—N2—N3118.46 (11)C9—C8—H8120.1
C9—N2—H2N125.6 (11)O3—C9—N2121.75 (12)
N3—N2—H2N114.0 (11)O3—C9—C8124.24 (12)
C10—N3—N2117.73 (11)N2—C9—C8113.95 (12)
C10—N3—H3N126.1 (11)O4—C10—N3121.47 (12)
N2—N3—H3N114.1 (11)O4—C10—C11122.51 (12)
C2—C1—C6118.84 (12)N3—C10—C11115.96 (12)
C2—C1—C7118.38 (13)C16—C11—C12119.75 (13)
C6—C1—C7122.74 (12)C16—C11—C10121.48 (12)
C3—C2—C1120.74 (13)C12—C11—C10118.62 (13)
C3—C2—H2119.6C13—C12—C11119.66 (14)
C1—C2—H2119.6C13—C12—H12120.2
C4—C3—C2118.63 (13)C11—C12—H12120.2
C4—C3—H3120.7C14—C13—C12120.04 (14)
C2—C3—H3120.7C14—C13—H13120.0
C3—C4—C5122.36 (13)C12—C13—H13120.0
C3—C4—N1118.74 (12)C13—C14—C15120.45 (13)
C5—C4—N1118.87 (13)C13—C14—H14119.8
C6—C5—C4118.45 (13)C15—C14—H14119.8
C6—C5—H5120.8C14—C15—C16119.70 (14)
C4—C5—H5120.8C14—C15—H15120.2
C5—C6—C1120.90 (13)C16—C15—H15120.2
C5—C6—H6119.5C15—C16—C11120.37 (13)
C1—C6—H6119.5C15—C16—H16119.8
C8—C7—C1126.49 (13)C11—C16—H16119.8
C8—C7—H7116.8
C9—N2—N3—C10172.40 (12)N3—N2—C9—O34.2 (2)
C6—C1—C2—C3−2.4 (2)N3—N2—C9—C8−178.39 (11)
C7—C1—C2—C3175.31 (13)C7—C8—C9—O3−9.0 (2)
C1—C2—C3—C40.3 (2)C7—C8—C9—N2173.72 (12)
C2—C3—C4—C52.4 (2)N2—N3—C10—O40.0 (2)
C2—C3—C4—N1−175.32 (13)N2—N3—C10—C11−177.37 (11)
O2—N1—C4—C3161.15 (13)O4—C10—C11—C16−146.43 (14)
O1—N1—C4—C3−17.9 (2)N3—C10—C11—C1630.87 (19)
O2—N1—C4—C5−16.63 (19)O4—C10—C11—C1229.2 (2)
O1—N1—C4—C5164.35 (13)N3—C10—C11—C12−153.50 (13)
C3—C4—C5—C6−2.8 (2)C16—C11—C12—C130.1 (2)
N1—C4—C5—C6174.94 (12)C10—C11—C12—C13−175.56 (12)
C4—C5—C6—C10.5 (2)C11—C12—C13—C141.1 (2)
C2—C1—C6—C52.0 (2)C12—C13—C14—C15−1.7 (2)
C7—C1—C6—C5−175.60 (13)C13—C14—C15—C161.0 (2)
C2—C1—C7—C8−179.69 (13)C14—C15—C16—C110.3 (2)
C6—C1—C7—C8−2.1 (2)C12—C11—C16—C15−0.8 (2)
C1—C7—C8—C9175.50 (12)C10—C11—C16—C15174.75 (13)
D—H···AD—HH···AD···AD—H···A
N2—H2n···O40.879 (10)2.273 (14)2.6470 (16)105.5 (11)
N2—H2n···O4i0.879 (10)2.050 (11)2.8721 (15)155.4 (13)
N3—H3n···O30.878 (10)2.354 (14)2.6687 (15)101.3 (10)
N3—H3n···O3ii0.878 (10)2.070 (11)2.9269 (15)165.0 (13)
C12—H12···O4iii0.952.563.4257 (18)151
C14—H14···O1iv0.952.583.2851 (19)132
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2n⋯O40.88 (1)2.27 (1)2.6470 (16)106 (1)
N2—H2n⋯O4i0.88 (1)2.05 (1)2.8721 (15)155 (1)
N3—H3n⋯O30.88 (1)2.35 (1)2.6687 (15)101 (1)
N3—H3n⋯O3ii0.88 (1)2.07 (1)2.9269 (15)165 (1)
C12—H12⋯O4iii0.952.563.4257 (18)151
C14—H14⋯O1iv0.952.583.2851 (19)132

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

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