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The title compound, C13H12N2O3, has been synthesized and characterized by X-ray diffraction and FT–IR spectroscopic analysis. The approximately planar molecule is in an E configuration with respect to the N—N bond [torsion angle −176.6 (2)°]. In the crystal structure, each hydrazide adopts the ketoamine form to link adjacent mol­ecules by the maximum possible number of O—H...O and N—H...O inter­molecular hydrogen bonds. A one-dimensional chain framework is formed by this hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002285/sg6059sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002285/sg6059Isup2.hkl
Contains datablock I

CCDC reference: 290511

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.173
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); 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.

2'-Acetyl-2-hydroxynaphthohydrazide top
Crystal data top
C13H12N2O3F(000) = 512
Mr = 244.25Dx = 1.351 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.266 (2) ÅCell parameters from 1313 reflections
b = 22.987 (8) Åθ = 2.6–24.1°
c = 8.503 (3) ŵ = 0.10 mm1
β = 101.329 (5)°T = 298 K
V = 1200.9 (7) Å3Needle, white
Z = 40.32 × 0.18 × 0.12 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2934 independent reflections
Radiation source: fine-focus sealed tube1283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 87
Tmin = 0.969, Tmax = 0.988k = 3016
7738 measured reflectionsl = 1011
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.079P)2]
where P = (Fo2 + 2Fc2)/3
2934 reflections(Δ/σ)max = 0.047
176 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.22 e Å3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.2466 (3)0.00993 (9)0.2198 (2)0.0463 (6)
O30.0894 (3)0.04576 (7)0.3333 (2)0.0510 (5)
N10.4219 (3)0.02753 (9)0.2311 (2)0.0449 (5)
C30.1907 (3)0.04474 (10)0.0934 (3)0.0374 (5)
C60.3053 (4)0.12221 (10)0.1955 (3)0.0421 (6)
H60.39400.12120.27120.051*
C40.0021 (3)0.08477 (9)0.0942 (2)0.0359 (5)
O20.2901 (3)0.04441 (8)0.01718 (19)0.0541 (5)
C10.4633 (4)0.06334 (11)0.3560 (3)0.0465 (6)
C50.1343 (3)0.08462 (10)0.2098 (3)0.0376 (6)
C130.0404 (4)0.12420 (10)0.0287 (3)0.0453 (6)
H130.04880.12470.10420.054*
C120.2134 (4)0.16386 (10)0.0450 (3)0.0449 (6)
O10.3459 (3)0.06341 (9)0.4566 (2)0.0749 (7)
C70.3507 (4)0.16258 (10)0.0689 (3)0.0426 (6)
C80.5263 (4)0.20211 (11)0.0500 (3)0.0571 (7)
H80.62090.20090.12170.069*
C20.6579 (4)0.10168 (13)0.3672 (3)0.0628 (8)
H2A0.77840.08490.44040.094*
H2B0.69440.10540.26320.094*
H2C0.62600.13940.40530.094*
C110.2537 (4)0.20553 (13)0.1694 (4)0.0669 (8)
H110.16340.20710.24400.080*
C90.5600 (5)0.24172 (13)0.0701 (4)0.0716 (9)
H90.67490.26790.07870.086*
C100.4229 (5)0.24347 (14)0.1815 (4)0.0807 (10)
H100.44740.27060.26410.097*
H150.503 (4)0.0262 (11)0.145 (3)0.071 (8)*
H160.165 (4)0.0054 (10)0.300 (3)0.065 (8)*
H140.190 (4)0.0504 (11)0.400 (3)0.074 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0452 (12)0.0554 (14)0.0444 (13)0.0139 (10)0.0238 (10)0.0077 (10)
O30.0507 (10)0.0645 (12)0.0453 (10)0.0121 (9)0.0279 (9)0.0113 (9)
N10.0410 (11)0.0589 (14)0.0399 (12)0.0118 (10)0.0205 (9)0.0046 (10)
C30.0333 (12)0.0433 (14)0.0388 (13)0.0038 (10)0.0149 (10)0.0036 (11)
C60.0389 (13)0.0493 (15)0.0427 (13)0.0002 (11)0.0193 (10)0.0039 (11)
C40.0337 (12)0.0387 (14)0.0382 (13)0.0020 (10)0.0143 (10)0.0041 (10)
O20.0541 (10)0.0682 (12)0.0488 (10)0.0135 (9)0.0313 (9)0.0088 (9)
C10.0482 (15)0.0564 (17)0.0394 (13)0.0094 (12)0.0193 (12)0.0034 (12)
C50.0376 (12)0.0420 (15)0.0357 (12)0.0020 (11)0.0136 (10)0.0025 (11)
C130.0440 (14)0.0530 (16)0.0439 (14)0.0005 (12)0.0214 (11)0.0028 (12)
C120.0444 (14)0.0420 (15)0.0510 (15)0.0001 (11)0.0159 (12)0.0026 (12)
O10.0855 (14)0.0943 (16)0.0599 (12)0.0286 (12)0.0506 (11)0.0233 (10)
C70.0403 (13)0.0386 (14)0.0517 (15)0.0028 (11)0.0157 (11)0.0036 (11)
C80.0522 (16)0.0540 (18)0.0699 (18)0.0062 (13)0.0237 (14)0.0000 (14)
C20.0620 (18)0.076 (2)0.0546 (17)0.0224 (15)0.0218 (14)0.0117 (14)
C110.0660 (19)0.068 (2)0.0745 (19)0.0140 (16)0.0339 (15)0.0249 (16)
C90.0641 (18)0.064 (2)0.092 (2)0.0220 (16)0.0279 (17)0.0175 (18)
C100.079 (2)0.074 (2)0.094 (2)0.0258 (18)0.0309 (18)0.0372 (19)
Geometric parameters (Å, º) top
N2—C31.331 (3)C13—C121.403 (3)
N2—N11.384 (3)C13—H130.9300
N2—H160.94 (2)C12—C111.413 (3)
O3—C51.366 (3)C12—C71.415 (3)
O3—H140.94 (3)C7—C81.412 (3)
N1—C11.328 (3)C8—C91.354 (4)
N1—H150.97 (3)C8—H80.9300
C3—O21.226 (2)C2—H2A0.9600
C3—C41.499 (3)C2—H2B0.9600
C6—C51.363 (3)C2—H2C0.9600
C6—C71.408 (3)C11—C101.361 (4)
C6—H60.9300C11—H110.9300
C4—C131.369 (3)C9—C101.399 (4)
C4—C51.424 (3)C9—H90.9300
C1—O11.233 (3)C10—H100.9300
C1—C21.492 (3)
C3—N2—N1120.61 (19)C13—C12—C11122.4 (2)
C3—N2—H16124.1 (15)C13—C12—C7118.7 (2)
N1—N2—H16114.9 (15)C11—C12—C7118.9 (2)
C5—O3—H14109.4 (17)C6—C7—C8123.1 (2)
C1—N1—N2117.95 (19)C6—C7—C12118.6 (2)
C1—N1—H15124.9 (15)C8—C7—C12118.3 (2)
N2—N1—H15117.2 (15)C9—C8—C7121.4 (2)
O2—C3—N2121.6 (2)C9—C8—H8119.3
O2—C3—C4121.8 (2)C7—C8—H8119.3
N2—C3—C4116.61 (19)C1—C2—H2A109.5
C5—C6—C7121.5 (2)C1—C2—H2B109.5
C5—C6—H6119.2H2A—C2—H2B109.5
C7—C6—H6119.2C1—C2—H2C109.5
C13—C4—C5118.4 (2)H2A—C2—H2C109.5
C13—C4—C3115.98 (19)H2B—C2—H2C109.5
C5—C4—C3125.6 (2)C10—C11—C12120.9 (3)
O1—C1—N1120.4 (2)C10—C11—H11119.6
O1—C1—C2123.1 (2)C12—C11—H11119.6
N1—C1—C2116.5 (2)C8—C9—C10120.3 (3)
C6—C5—O3121.5 (2)C8—C9—H9119.8
C6—C5—C4120.3 (2)C10—C9—H9119.8
O3—C5—C4118.14 (19)C11—C10—C9120.2 (3)
C4—C13—C12122.4 (2)C11—C10—H10119.9
C4—C13—H13118.8C9—C10—H10119.9
C12—C13—H13118.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H16···O30.94 (2)1.91 (2)2.615 (3)130 (2)
O3—H14···O1i0.94 (3)1.73 (3)2.658 (3)172 (2)
N1—H15···O2ii0.97 (3)1.90 (3)2.829 (3)161 (2)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z.
 

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