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The molecule of the title compound, C14H11N3O5, is approximately planar, the dihedral angles between the two aromatic rings being 4.63 (7)°. O—H...N, N—H...O and O—H...O hydrogen bonds and π–π stacking inter­actions help to consolidate the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023233/hb2084sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023233/hb2084Isup2.hkl
Contains datablock I

CCDC reference: 613700

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 1288.60 Ang-3 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT414_ALERT_2_C Short Intra D-H..H-X H2B .. H14A .. 1.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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 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: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.

5-Nitrosalicylaldehyde (2-hydroxybenzoyl)hydrazone top
Crystal data top
C14H11N3O5F(000) = 624
Mr = 301.26Dx = 1.553 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2939 reflections
a = 7.645 (3) Åθ = 3.1–27.5°
b = 6.751 (3) ŵ = 0.12 mm1
c = 24.994 (11) ÅT = 293 K
β = 92.473 (9)°Chip, colorless
V = 1288.6 (9) Å30.40 × 0.15 × 0.10 mm
Z = 4
Data collection top
Rigaku Weissenberg IP
diffractometer
2939 independent reflections
Radiation source: fine-focus sealed tube2101 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: ψ scan
(TEXRAY; Molecular Structure Corporation, 1999)
h = 99
Tmin = 0.978, Tmax = 0.988k = 88
11290 measured reflectionsl = 3231
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)] = 0.040Hydrogen site location: difmap and geom
wR(F2) = 0.131H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0809P)2]
where P = (Fo2 + 2Fc2)/3
2939 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.21 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
C10.28834 (18)0.6284 (2)0.12442 (6)0.0373 (3)
C20.32468 (18)0.7406 (2)0.07870 (5)0.0358 (3)
C30.39886 (18)0.9272 (2)0.08554 (6)0.0368 (3)
H3A0.42211.00430.05590.053 (5)*
C40.43803 (18)0.9981 (2)0.13654 (5)0.0353 (3)
C50.40496 (19)0.8872 (2)0.18154 (6)0.0402 (3)
H5A0.43310.93640.21560.059 (5)*
C60.3304 (2)0.7042 (2)0.17522 (6)0.0426 (4)
H6A0.30730.62910.20530.061 (5)*
C70.2908 (2)0.6683 (2)0.02415 (6)0.0421 (4)
H7A0.31180.75100.00460.061 (5)*
C80.16326 (19)0.2517 (2)0.04980 (5)0.0377 (3)
C90.14129 (18)0.1995 (2)0.10724 (6)0.0362 (3)
C100.07759 (19)0.0103 (2)0.12123 (6)0.0400 (3)
C110.0585 (2)0.0422 (3)0.17506 (7)0.0497 (4)
H11A0.01490.16660.18450.067 (6)*
C120.1034 (2)0.0881 (3)0.21415 (6)0.0504 (4)
H12A0.08990.05130.25000.059 (5)*
C130.1685 (2)0.2734 (3)0.20104 (6)0.0489 (4)
H13A0.20020.36030.22780.051 (5)*
C140.1860 (2)0.3287 (2)0.14807 (6)0.0435 (4)
H14A0.22850.45420.13930.060 (6)*
N10.23313 (17)0.4939 (2)0.01539 (5)0.0415 (3)
N20.20856 (19)0.4402 (2)0.03749 (5)0.0456 (3)
H2B0.22190.52580.06250.055 (6)*
N30.52248 (17)1.1896 (2)0.14243 (5)0.0419 (3)
O10.21312 (15)0.44866 (17)0.12172 (5)0.0489 (3)
H1B0.18220.41720.08800.078 (7)*
O20.1422 (2)0.12946 (19)0.01428 (4)0.0609 (4)
O30.54438 (19)1.26019 (18)0.18736 (5)0.0600 (4)
O40.57015 (17)1.27376 (18)0.10198 (5)0.0559 (3)
O50.03168 (18)0.12711 (18)0.08534 (5)0.0566 (3)
H5B0.03750.07000.05080.075 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0372 (6)0.0344 (8)0.0405 (7)0.0005 (6)0.0018 (6)0.0009 (6)
C20.0397 (7)0.0348 (8)0.0326 (7)0.0006 (6)0.0001 (5)0.0017 (6)
C30.0447 (7)0.0341 (8)0.0317 (7)0.0020 (6)0.0022 (6)0.0011 (5)
C40.0382 (7)0.0320 (7)0.0356 (7)0.0003 (6)0.0001 (6)0.0040 (6)
C50.0462 (7)0.0425 (9)0.0318 (7)0.0023 (7)0.0007 (6)0.0038 (6)
C60.0496 (8)0.0452 (9)0.0332 (7)0.0030 (7)0.0049 (6)0.0055 (6)
C70.0541 (8)0.0364 (8)0.0354 (7)0.0047 (7)0.0012 (6)0.0010 (6)
C80.0443 (7)0.0354 (7)0.0331 (7)0.0053 (6)0.0021 (6)0.0008 (6)
C90.0380 (6)0.0355 (8)0.0348 (7)0.0018 (6)0.0035 (6)0.0020 (6)
C100.0431 (7)0.0364 (8)0.0404 (8)0.0004 (6)0.0019 (6)0.0039 (6)
C110.0570 (9)0.0465 (10)0.0449 (9)0.0001 (8)0.0042 (7)0.0126 (7)
C120.0545 (9)0.0622 (11)0.0342 (8)0.0070 (8)0.0013 (7)0.0098 (7)
C130.0505 (8)0.0612 (11)0.0350 (8)0.0018 (8)0.0019 (6)0.0058 (7)
C140.0479 (8)0.0435 (9)0.0387 (8)0.0052 (7)0.0016 (6)0.0017 (7)
N10.0525 (7)0.0386 (7)0.0328 (6)0.0045 (6)0.0035 (5)0.0045 (5)
N20.0691 (8)0.0368 (7)0.0304 (6)0.0116 (7)0.0034 (6)0.0012 (5)
N30.0473 (7)0.0360 (7)0.0421 (7)0.0006 (6)0.0021 (6)0.0049 (5)
O10.0582 (6)0.0382 (6)0.0501 (7)0.0121 (5)0.0013 (5)0.0034 (5)
O20.1014 (10)0.0455 (7)0.0354 (6)0.0254 (7)0.0025 (6)0.0031 (5)
O30.0871 (9)0.0458 (7)0.0459 (7)0.0064 (7)0.0101 (6)0.0145 (6)
O40.0710 (8)0.0443 (7)0.0529 (7)0.0184 (6)0.0092 (6)0.0018 (5)
O50.0843 (9)0.0389 (7)0.0466 (7)0.0168 (6)0.0021 (6)0.0033 (5)
Geometric parameters (Å, º) top
C1—O11.3430 (19)C9—C141.396 (2)
C1—C61.394 (2)C9—C101.405 (2)
C1—C21.409 (2)C10—O51.348 (2)
C2—C31.389 (2)C10—C111.393 (2)
C2—C71.461 (2)C11—C121.370 (3)
C3—C41.382 (2)C11—H11A0.9300
C3—H3A0.9300C12—C131.380 (3)
C4—C51.383 (2)C12—H12A0.9300
C4—N31.450 (2)C13—C141.377 (2)
C5—C61.366 (2)C13—H13A0.9300
C5—H5A0.9300C14—H14A0.9300
C6—H6A0.9300N1—N21.3755 (17)
C7—N11.273 (2)N2—H2B0.8600
C7—H7A0.9300N3—O31.2248 (17)
C8—O21.2277 (19)N3—O41.2287 (18)
C8—N21.351 (2)O1—H1B0.8903
C8—C91.481 (2)O5—H5B0.9460
O1—C1—C6117.34 (14)C10—C9—C8118.75 (13)
O1—C1—C2122.96 (13)O5—C10—C11116.62 (15)
C6—C1—C2119.71 (14)O5—C10—C9123.88 (14)
C3—C2—C1118.79 (13)C11—C10—C9119.51 (15)
C3—C2—C7118.23 (13)C12—C11—C10120.42 (16)
C1—C2—C7122.97 (14)C12—C11—H11A119.8
C4—C3—C2119.90 (13)C10—C11—H11A119.8
C4—C3—H3A120.0C11—C12—C13120.77 (15)
C2—C3—H3A120.0C11—C12—H12A119.6
C3—C4—C5121.51 (14)C13—C12—H12A119.6
C3—C4—N3118.69 (13)C14—C13—C12119.55 (16)
C5—C4—N3119.75 (12)C14—C13—H13A120.2
C6—C5—C4119.02 (13)C12—C13—H13A120.2
C6—C5—H5A120.5C13—C14—C9121.13 (16)
C4—C5—H5A120.5C13—C14—H14A119.4
C5—C6—C1121.06 (14)C9—C14—H14A119.4
C5—C6—H6A119.5C7—N1—N2116.18 (13)
C1—C6—H6A119.5C8—N2—N1119.36 (13)
N1—C7—C2121.06 (14)C8—N2—H2B120.3
N1—C7—H7A119.5N1—N2—H2B120.3
C2—C7—H7A119.5O3—N3—O4122.74 (14)
O2—C8—N2120.58 (13)O3—N3—C4118.87 (13)
O2—C8—C9121.89 (14)O4—N3—C4118.39 (12)
N2—C8—C9117.53 (13)C1—O1—H1B111.0
C14—C9—C10118.60 (14)C10—O5—H5B108.9
C14—C9—C8122.62 (14)
O1—C1—C2—C3178.43 (13)C14—C9—C10—O5179.44 (15)
C6—C1—C2—C31.3 (2)C8—C9—C10—O51.2 (2)
O1—C1—C2—C72.7 (2)C14—C9—C10—C110.9 (2)
C6—C1—C2—C7177.55 (14)C8—C9—C10—C11179.10 (14)
C1—C2—C3—C41.0 (2)O5—C10—C11—C12179.47 (16)
C7—C2—C3—C4177.91 (14)C9—C10—C11—C120.9 (2)
C2—C3—C4—C50.0 (2)C10—C11—C12—C130.1 (3)
C2—C3—C4—N3177.30 (12)C11—C12—C13—C140.9 (3)
C3—C4—C5—C60.6 (2)C12—C13—C14—C90.8 (2)
N3—C4—C5—C6177.92 (13)C10—C9—C14—C130.1 (2)
C4—C5—C6—C10.3 (2)C8—C9—C14—C13178.19 (14)
O1—C1—C6—C5179.07 (14)C2—C7—N1—N2179.01 (14)
C2—C1—C6—C50.7 (2)O2—C8—N2—N10.8 (2)
C3—C2—C7—N1175.65 (14)C9—C8—N2—N1178.92 (13)
C1—C2—C7—N13.2 (2)C7—N1—N2—C8173.89 (14)
O2—C8—C9—C14171.62 (15)C3—C4—N3—O3174.07 (14)
N2—C8—C9—C148.1 (2)C5—C4—N3—O38.5 (2)
O2—C8—C9—C106.5 (2)C3—C4—N3—O46.4 (2)
N2—C8—C9—C10173.81 (13)C5—C4—N3—O4171.01 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O4i0.862.343.070 (2)143
O1—H1B···N10.891.942.686 (2)140
O1—H1B···O5ii0.892.552.9822 (18)111
O5—H5B···O20.951.792.5960 (17)141
O5—H5B···O2ii0.952.212.873 (2)126
Symmetry codes: (i) x+1, y+2, z; (ii) x, y, z.
 

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