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The molecule of the title compound, C15H15N3O4, is non-planar. The ethyl­vanillin group makes a dihedral angle of 7.68 (7)° with the nitro­phenyl­hydrazine mean plane. A trifurcated intra/inter­molecular O—H...(O,O,O) hydrogen-bond system helps to establish the mol­ecular conformation and consolidate the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032617/hb6287sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032617/hb6287Isup2.hkl
Contains datablock I

CCDC reference: 289758

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.110
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - N3 .. 6.12 su PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

(E)-1-(3-Ethoxy-4-hydroxybenzylidene)-2-(4-nitrophenyl)hydrazine top
Crystal data top
C15H15N3O4F(000) = 632
Mr = 301.30Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2008 reflections
a = 10.148 (2) Åθ = 2.6–25.9°
b = 9.0980 (19) ŵ = 0.10 mm1
c = 15.967 (3) ÅT = 294 K
β = 103.868 (3)°Block, yellow
V = 1431.2 (5) Å30.34 × 0.30 × 0.24 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2904 independent reflections
Radiation source: fine-focus sealed tube1758 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.960, Tmax = 0.975k = 911
7792 measured reflectionsl = 1917
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap (O-H and N-H) and geom (C-H)
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.2257P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
2904 reflectionsΔρmax = 0.18 e Å3
209 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0170 (18)
Special details top

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.53401 (11)0.13835 (14)1.09950 (8)0.0518 (4)
O20.73380 (15)0.04459 (16)1.17677 (9)0.0595 (4)
H20.658 (3)0.033 (3)1.1874 (15)0.091 (9)*
O31.44556 (16)0.65773 (18)0.70004 (10)0.0756 (5)
O41.54473 (15)0.49590 (17)0.79152 (11)0.0728 (5)
N10.94799 (14)0.37228 (16)0.91562 (9)0.0432 (4)
N20.96068 (17)0.48029 (19)0.85831 (10)0.0482 (4)
H2A0.898 (2)0.537 (2)0.8385 (13)0.066 (7)*
N31.44349 (18)0.56781 (19)0.75697 (11)0.0527 (4)
C10.83267 (18)0.3609 (2)0.93394 (11)0.0436 (5)
H10.76320.42460.90790.052*
C20.80658 (17)0.25120 (19)0.99452 (11)0.0392 (4)
C30.90503 (17)0.1512 (2)1.03484 (11)0.0455 (5)
H30.98940.15111.02160.055*
C40.87906 (17)0.0522 (2)1.09430 (12)0.0475 (5)
H40.94570.01461.12030.057*
C50.75509 (17)0.0516 (2)1.11539 (11)0.0417 (4)
C60.65312 (17)0.1485 (2)1.07363 (11)0.0393 (4)
C70.67949 (16)0.2467 (2)1.01388 (11)0.0419 (4)
H70.61170.31090.98610.050*
C80.42008 (16)0.2213 (2)1.05285 (12)0.0472 (5)
H8A0.39740.19280.99260.057*
H8B0.44110.32551.05650.057*
C90.30317 (18)0.1899 (2)1.09259 (13)0.0600 (6)
H9A0.28180.08701.08730.090*
H9B0.22550.24591.06340.090*
H9C0.32740.21671.15250.090*
C101.08024 (17)0.49957 (19)0.83417 (10)0.0378 (4)
C111.18909 (18)0.4025 (2)0.86025 (11)0.0452 (5)
H111.18100.32220.89470.054*
C121.30770 (18)0.4252 (2)0.83541 (11)0.0469 (5)
H121.38020.36080.85310.056*
C131.31866 (18)0.5447 (2)0.78386 (11)0.0409 (4)
C141.21158 (19)0.6407 (2)0.75676 (11)0.0449 (5)
H141.22000.71990.72160.054*
C151.09325 (18)0.6192 (2)0.78166 (11)0.0436 (5)
H151.02130.68420.76370.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0323 (7)0.0686 (9)0.0568 (8)0.0069 (6)0.0153 (6)0.0148 (7)
O20.0484 (9)0.0644 (10)0.0719 (10)0.0104 (7)0.0267 (8)0.0204 (7)
O30.0825 (11)0.0840 (12)0.0707 (10)0.0195 (9)0.0388 (9)0.0117 (9)
O40.0515 (9)0.0759 (11)0.0981 (12)0.0046 (8)0.0321 (9)0.0028 (9)
N10.0408 (9)0.0491 (10)0.0411 (9)0.0051 (7)0.0123 (7)0.0002 (7)
N20.0425 (10)0.0517 (11)0.0519 (10)0.0053 (8)0.0140 (8)0.0110 (8)
N30.0578 (11)0.0536 (11)0.0531 (10)0.0126 (9)0.0260 (9)0.0102 (9)
C10.0380 (10)0.0505 (12)0.0419 (10)0.0004 (9)0.0087 (8)0.0053 (9)
C20.0362 (10)0.0442 (11)0.0378 (10)0.0031 (8)0.0098 (8)0.0067 (8)
C30.0340 (10)0.0549 (12)0.0508 (11)0.0006 (9)0.0167 (9)0.0047 (9)
C40.0367 (10)0.0531 (12)0.0532 (12)0.0117 (9)0.0119 (9)0.0029 (10)
C50.0405 (10)0.0416 (11)0.0440 (10)0.0001 (9)0.0119 (8)0.0009 (9)
C60.0318 (9)0.0469 (11)0.0400 (10)0.0003 (8)0.0104 (8)0.0044 (8)
C70.0336 (10)0.0502 (11)0.0413 (10)0.0037 (8)0.0079 (8)0.0006 (9)
C80.0334 (10)0.0575 (12)0.0503 (11)0.0040 (9)0.0093 (9)0.0045 (9)
C90.0359 (11)0.0759 (15)0.0693 (14)0.0005 (10)0.0150 (10)0.0069 (11)
C100.0386 (10)0.0414 (10)0.0328 (9)0.0020 (8)0.0073 (8)0.0012 (8)
C110.0470 (11)0.0412 (11)0.0494 (11)0.0029 (9)0.0155 (9)0.0102 (9)
C120.0446 (11)0.0443 (11)0.0537 (12)0.0064 (9)0.0157 (9)0.0056 (9)
C130.0434 (10)0.0429 (11)0.0395 (10)0.0045 (9)0.0158 (8)0.0042 (8)
C140.0580 (12)0.0403 (11)0.0366 (10)0.0046 (9)0.0116 (9)0.0054 (8)
C150.0462 (11)0.0420 (11)0.0401 (10)0.0037 (9)0.0051 (9)0.0043 (8)
Geometric parameters (Å, º) top
O1—C61.371 (2)C5—C61.401 (2)
O1—C81.431 (2)C6—C71.379 (2)
O2—C51.369 (2)C7—H70.9300
O2—H20.83 (3)C8—C91.501 (2)
O3—N31.227 (2)C8—H8A0.9700
O4—N31.231 (2)C8—H8B0.9700
N1—C11.277 (2)C9—H9A0.9600
N1—N21.370 (2)C9—H9B0.9600
N2—C101.370 (2)C9—H9C0.9600
N2—H2A0.82 (2)C10—C111.397 (2)
N3—C131.447 (2)C10—C151.399 (2)
C1—C21.458 (2)C11—C121.370 (2)
C1—H10.9300C11—H110.9300
C2—C31.390 (2)C12—C131.384 (2)
C2—C71.397 (2)C12—H120.9300
C3—C41.379 (2)C13—C141.380 (2)
C3—H30.9300C14—C151.366 (2)
C4—C51.378 (2)C14—H140.9300
C4—H40.9300C15—H150.9300
C6—O1—C8117.91 (13)O1—C8—C9107.54 (15)
C5—O2—H2112.1 (17)O1—C8—H8A110.2
C1—N1—N2116.70 (16)C9—C8—H8A110.2
C10—N2—N1120.76 (16)O1—C8—H8B110.2
C10—N2—H2A118.1 (15)C9—C8—H8B110.2
N1—N2—H2A121.1 (15)H8A—C8—H8B108.5
O3—N3—O4121.71 (17)C8—C9—H9A109.5
O3—N3—C13119.23 (18)C8—C9—H9B109.5
O4—N3—C13119.06 (17)H9A—C9—H9B109.5
N1—C1—C2122.00 (17)C8—C9—H9C109.5
N1—C1—H1119.0H9A—C9—H9C109.5
C2—C1—H1119.0H9B—C9—H9C109.5
C3—C2—C7118.54 (17)N2—C10—C11121.71 (16)
C3—C2—C1122.06 (16)N2—C10—C15119.04 (16)
C7—C2—C1119.40 (16)C11—C10—C15119.26 (16)
C4—C3—C2120.76 (16)C12—C11—C10120.34 (17)
C4—C3—H3119.6C12—C11—H11119.8
C2—C3—H3119.6C10—C11—H11119.8
C5—C4—C3120.47 (17)C11—C12—C13119.46 (17)
C5—C4—H4119.8C11—C12—H12120.3
C3—C4—H4119.8C13—C12—H12120.3
O2—C5—C4119.16 (17)C14—C13—C12120.93 (17)
O2—C5—C6121.19 (16)C14—C13—N3119.63 (17)
C4—C5—C6119.65 (17)C12—C13—N3119.44 (17)
O1—C6—C7125.69 (16)C15—C14—C13119.93 (17)
O1—C6—C5114.71 (16)C15—C14—H14120.0
C7—C6—C5119.56 (16)C13—C14—H14120.0
C6—C7—C2120.96 (16)C14—C15—C10120.08 (17)
C6—C7—H7119.5C14—C15—H15120.0
C2—C7—H7119.5C10—C15—H15120.0
C1—N1—N2—C10179.31 (16)C1—C2—C7—C6177.22 (16)
N2—N1—C1—C2179.51 (15)C6—O1—C8—C9179.21 (16)
N1—C1—C2—C31.0 (3)N1—N2—C10—C116.1 (3)
N1—C1—C2—C7178.21 (17)N1—N2—C10—C15174.27 (15)
C7—C2—C3—C41.6 (3)N2—C10—C11—C12179.65 (17)
C1—C2—C3—C4177.57 (16)C15—C10—C11—C120.7 (3)
C2—C3—C4—C50.6 (3)C10—C11—C12—C130.3 (3)
C3—C4—C5—O2177.81 (16)C11—C12—C13—C140.4 (3)
C3—C4—C5—C62.5 (3)C11—C12—C13—N3179.42 (16)
C8—O1—C6—C79.3 (3)O3—N3—C13—C1411.4 (3)
C8—O1—C6—C5172.81 (15)O4—N3—C13—C14169.09 (16)
O2—C5—C6—O10.2 (2)O3—N3—C13—C12167.68 (17)
C4—C5—C6—O1179.89 (16)O4—N3—C13—C1211.9 (3)
O2—C5—C6—C7178.20 (16)C12—C13—C14—C150.7 (3)
C4—C5—C6—C72.1 (3)N3—C13—C14—C15179.77 (16)
O1—C6—C7—C2177.63 (16)C13—C14—C15—C100.4 (3)
C5—C6—C7—C20.2 (3)N2—C10—C15—C14180.00 (16)
C3—C2—C7—C62.0 (3)C11—C10—C15—C140.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.83 (3)2.27 (2)2.6840 (19)111 (2)
O2—H2···O4i0.83 (3)2.26 (3)2.987 (2)146 (2)
O2—H2···O3i0.83 (3)2.49 (3)3.205 (2)145 (2)
Symmetry code: (i) x1, y+1/2, z+1/2.
 

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