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Excluding H atoms, the title molecule, C12H15O3N3, is approximately planar. Glide-related molecules are linked by intermolecular O—H...O hydrogen bonds into a chain structure running along [101]. The crystal packing is further stabilized by π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032672/ci6504sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032672/ci6504Isup2.hkl
Contains datablock I

CCDC reference: 262468

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.133
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H13 ... ?
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 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 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: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

3-(Hydroxyimino)butan-2-one (4-methoxybenzoyl)hydrazone top
Crystal data top
C12H15N3O3F(000) = 528
Mr = 249.27Dx = 1.324 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 10756 reflections
a = 6.8829 (14) Åθ = 3.1–27.5°
b = 23.589 (5) ŵ = 0.10 mm1
c = 7.7372 (15) ÅT = 296 K
β = 95.66 (3)°Prism, yellow
V = 1250.1 (4) Å30.39 × 0.26 × 0.22 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2847 independent reflections
Radiation source: fine-focus sealed tube2092 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 88
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 3030
Tmin = 0.969, Tmax = 0.978l = 109
12054 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.077P)2 + 0.0771P]
where P = (Fo2 + 2Fc2)/3
2847 reflections(Δ/σ)max = 0.001
169 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.18 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.59233 (15)0.79936 (5)0.33748 (15)0.0406 (3)
N20.71661 (15)0.67305 (4)0.54605 (15)0.0391 (3)
N30.62210 (16)0.62664 (5)0.60587 (16)0.0432 (3)
O10.69009 (14)0.84679 (4)0.28100 (15)0.0489 (3)
O20.90419 (13)0.57946 (4)0.68091 (15)0.0525 (3)
O30.33317 (17)0.38699 (4)0.87553 (17)0.0639 (4)
C10.92557 (19)0.76493 (6)0.4257 (2)0.0502 (4)
C20.70796 (17)0.76102 (5)0.40479 (17)0.0357 (3)
C30.60694 (17)0.71029 (5)0.46378 (17)0.0372 (3)
C40.3902 (2)0.70507 (7)0.4215 (2)0.0572 (4)
C50.72511 (18)0.58123 (5)0.67079 (18)0.0387 (3)
C60.60856 (19)0.53238 (5)0.72376 (17)0.0379 (3)
C70.40887 (19)0.52634 (6)0.68215 (18)0.0417 (3)
C80.3104 (2)0.47842 (6)0.72998 (19)0.0451 (3)
C90.4133 (2)0.43586 (6)0.82185 (19)0.0458 (3)
C100.6127 (2)0.44143 (6)0.8657 (2)0.0519 (4)
C110.7080 (2)0.48898 (6)0.8164 (2)0.0473 (4)
C120.1271 (3)0.38041 (8)0.8473 (3)0.0721 (6)
H1A0.97570.75480.31850.075*
H1B0.97690.73950.51580.075*
H1C0.96400.80300.45630.075*
H4A0.36100.67030.35980.086*
H4B0.34310.73650.35070.086*
H4C0.32780.70500.52720.086*
H70.33960.55500.62090.050*
H80.17670.47490.70060.054*
H100.68160.41300.92840.062*
H110.84190.49220.84550.057*
H12A0.06470.40980.90760.108*
H12B0.09090.34410.89000.108*
H12C0.08650.38290.72520.108*
H130.49680.62650.60200.052*
H140.596 (2)0.8670 (7)0.237 (2)0.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0378 (6)0.0383 (6)0.0461 (7)0.0051 (5)0.0060 (5)0.0049 (5)
N20.0361 (5)0.0350 (6)0.0459 (7)0.0012 (4)0.0024 (5)0.0021 (5)
N30.0349 (5)0.0379 (6)0.0566 (8)0.0019 (4)0.0031 (5)0.0075 (5)
O10.0445 (5)0.0372 (5)0.0657 (7)0.0071 (4)0.0082 (5)0.0126 (5)
O20.0374 (5)0.0374 (5)0.0811 (8)0.0017 (4)0.0026 (5)0.0002 (5)
O30.0650 (7)0.0403 (6)0.0886 (9)0.0035 (5)0.0191 (6)0.0139 (6)
C10.0340 (7)0.0485 (8)0.0672 (10)0.0008 (6)0.0009 (6)0.0159 (7)
C20.0323 (6)0.0372 (7)0.0375 (7)0.0042 (5)0.0027 (5)0.0002 (5)
C30.0327 (6)0.0397 (7)0.0392 (7)0.0024 (5)0.0033 (5)0.0006 (5)
C40.0339 (7)0.0656 (10)0.0712 (11)0.0018 (7)0.0012 (7)0.0215 (8)
C50.0398 (7)0.0332 (6)0.0422 (7)0.0002 (5)0.0004 (5)0.0056 (5)
C60.0434 (7)0.0318 (6)0.0382 (7)0.0008 (5)0.0029 (5)0.0035 (5)
C70.0427 (7)0.0374 (7)0.0448 (8)0.0016 (5)0.0030 (6)0.0015 (6)
C80.0423 (7)0.0432 (8)0.0505 (8)0.0018 (6)0.0076 (6)0.0016 (6)
C90.0559 (8)0.0335 (7)0.0499 (8)0.0026 (6)0.0149 (6)0.0013 (6)
C100.0564 (9)0.0375 (7)0.0609 (10)0.0076 (6)0.0017 (7)0.0075 (7)
C110.0440 (7)0.0394 (7)0.0571 (9)0.0024 (6)0.0015 (6)0.0025 (6)
C120.0639 (10)0.0538 (10)0.1031 (16)0.0128 (8)0.0312 (10)0.0093 (9)
Geometric parameters (Å, º) top
N1—C21.2810 (16)C4—H4B0.96
N2—C31.2852 (16)C4—H4C0.96
N2—N31.3767 (15)C5—C61.4846 (18)
N3—C51.3537 (17)C6—C71.3877 (19)
O1—N11.3978 (15)C6—C111.3905 (19)
O2—C51.2280 (15)C7—C81.3868 (19)
O3—C91.3605 (17)C7—H70.93
O3—C121.422 (2)C8—C91.384 (2)
N3—H130.86C8—H80.93
O1—H140.850 (9)C9—C101.387 (2)
C1—C21.4933 (18)C10—C111.372 (2)
C1—H1A0.96C10—H100.93
C1—H1B0.96C11—H110.93
C1—H1C0.96C12—H12A0.96
C2—C31.4786 (18)C12—H12B0.96
C3—C41.5006 (18)C12—H12C0.96
C4—H4A0.96
N1—C2—C1125.22 (12)C5—N3—H13119.8
N1—C2—C3113.87 (11)C6—C7—H7119.3
N2—C3—C2115.77 (11)C6—C11—H11119.3
N2—C3—C4125.07 (12)C7—C6—C5124.44 (11)
N3—C5—C6116.05 (11)C7—C6—C11118.03 (12)
O2—C5—N3122.42 (12)C7—C8—H8120.3
O2—C5—C6121.49 (12)C8—C7—C6121.38 (12)
O3—C9—C8124.68 (13)C8—C7—H7119.3
O3—C9—C10115.27 (13)C8—C9—C10120.04 (13)
C2—N1—O1113.16 (10)C9—C8—C7119.31 (12)
C3—N2—N3115.85 (10)C9—C8—H8120.3
C5—N3—N2120.43 (11)C9—C10—H10120.1
C9—O3—C12118.29 (13)C10—C11—C6121.36 (13)
N1—O1—H14101.6 (14)C10—C11—H11119.3
N2—N3—H13119.8C11—C6—C5117.50 (12)
O3—C12—H12A109.5C11—C10—C9119.88 (13)
O3—C12—H12B109.5C11—C10—H10120.1
O3—C12—H12C109.5H1A—C1—H1B109.5
C2—C1—H1C109.5H1A—C1—H1C109.5
C2—C1—H1A109.5H1B—C1—H1C109.5
C2—C1—H1B109.5H4A—C4—H4B109.5
C2—C3—C4119.14 (11)H4A—C4—H4C109.5
C3—C2—C1120.91 (11)H4B—C4—H4C109.5
C3—C4—H4A109.5H12A—C12—H12B109.5
C3—C4—H4B109.5H12A—C12—H12C109.5
C3—C4—H4C109.5H12B—C12—H12C109.5
N1—C2—C3—N2174.00 (12)C1—C2—C3—C4172.84 (14)
N1—C2—C3—C47.35 (19)C3—N2—N3—C5170.08 (13)
N2—N3—C5—O20.7 (2)C5—C6—C7—C8177.33 (12)
N2—N3—C5—C6177.14 (11)C5—C6—C11—C10177.91 (13)
N3—N2—C3—C2178.01 (11)C6—C7—C8—C90.3 (2)
N3—N2—C3—C43.4 (2)C7—C6—C11—C100.0 (2)
N3—C5—C6—C712.42 (19)C7—C8—C9—O3179.88 (13)
N3—C5—C6—C11169.82 (13)C7—C8—C9—C100.2 (2)
O1—N1—C2—C10.7 (2)C8—C9—C10—C110.6 (2)
O1—N1—C2—C3179.47 (11)C9—C10—C11—C60.5 (2)
O2—C5—C6—C7165.48 (13)C11—C6—C7—C80.4 (2)
O2—C5—C6—C1112.3 (2)C12—O3—C9—C84.9 (2)
O3—C9—C10—C11179.46 (14)C12—O3—C9—C10175.07 (15)
C1—C2—C3—N25.80 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H14···O2i0.85 (1)1.84 (1)2.683 (1)168 (2)
Symmetry code: (i) x1/2, y+3/2, z1/2.
 

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