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The synthesis of the title compound, C9H9N3O3, was achieved by the condensation of 3,4-methyl­ene­dioxy­benz­aldehyde with semicarbazide hydro­chloride. The mol­ecule is approximately planar: the dihedral angles of the 3,4-methyl­ene­dioxy­benzene and amide moieties with the hydrazone moiety are 10.2 (2) and 8.9 (3)°, respectively. Intra- and intermolecular hydrogen bonds generate a two-dimensional network. Aromatic stacking interactions are also found in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006634/cf6335sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006634/cf6335Isup2.hkl
Contains datablock I

CCDC reference: 238818

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.101
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O17 PLAT432_ALERT_2_C Short Inter X...Y Contact O17 .. C10 .. 3.00 Ang.
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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3,4-methylenedioxybenzaldehyde semicarbazone top
Crystal data top
C9H9N3O3F(000) = 432
Mr = 207.19Dx = 1.467 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 820 reflections
a = 17.698 (7) Åθ = 2.0–21.1°
b = 4.475 (2) ŵ = 0.11 mm1
c = 12.084 (5) ÅT = 293 K
β = 101.353 (6)°Prism, pink
V = 938.2 (7) Å30.26 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1265 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 26.4°, θmin = 1.2°
φ and ω scansh = 1522
5042 measured reflectionsk = 55
1916 independent reflectionsl = 1514
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041All H-atom parameters refined
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.0571P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1916 reflectionsΔρmax = 0.14 e Å3
173 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (2)
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
O10.49013 (6)0.2965 (3)0.13497 (9)0.0454 (4)
O170.93936 (8)0.2911 (4)0.43700 (12)0.0708 (5)
O180.91425 (7)0.4054 (4)0.24658 (11)0.0689 (5)
N10.57967 (9)0.0693 (4)0.13051 (13)0.0444 (4)
H1A0.5544 (11)0.143 (4)0.1969 (18)0.055 (6)*
H1B0.6194 (12)0.164 (5)0.0861 (17)0.063 (6)*
N20.58712 (8)0.2665 (4)0.01553 (12)0.0424 (4)
H20.5649 (10)0.409 (4)0.0528 (16)0.050 (5)*
N30.65177 (7)0.1193 (3)0.07217 (11)0.0395 (4)
C10.54933 (9)0.1651 (4)0.08670 (13)0.0352 (4)
C20.67542 (10)0.1998 (5)0.17424 (14)0.0440 (5)
H30.6513 (10)0.349 (4)0.2064 (16)0.054 (6)*
C110.74433 (9)0.0718 (4)0.24503 (13)0.0412 (4)
C120.76112 (11)0.1410 (5)0.35905 (15)0.0485 (5)
H120.7305 (9)0.271 (4)0.3859 (15)0.042 (5)*
C130.82591 (11)0.0284 (5)0.43159 (15)0.0514 (5)
H130.8387 (10)0.082 (4)0.5104 (17)0.054 (5)*
C140.87233 (10)0.1538 (4)0.38466 (15)0.0469 (5)
C150.85703 (10)0.2223 (4)0.27113 (15)0.0448 (5)
C160.79397 (10)0.1158 (4)0.19878 (15)0.0453 (5)
H160.7839 (9)0.170 (4)0.1183 (16)0.044 (5)*
C100.96719 (13)0.4488 (7)0.35096 (19)0.0630 (6)
H10A0.9714 (13)0.655 (6)0.371 (2)0.082 (8)*
H10B1.0170 (13)0.362 (5)0.3440 (19)0.075 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0450 (7)0.0498 (8)0.0355 (7)0.0041 (6)0.0060 (5)0.0029 (6)
O170.0601 (9)0.0877 (11)0.0542 (9)0.0262 (8)0.0141 (7)0.0006 (8)
O180.0578 (9)0.0884 (11)0.0555 (8)0.0301 (8)0.0011 (7)0.0033 (8)
N10.0473 (9)0.0470 (10)0.0340 (8)0.0008 (8)0.0035 (7)0.0030 (8)
N20.0425 (8)0.0483 (10)0.0321 (8)0.0101 (7)0.0031 (6)0.0022 (7)
N30.0368 (7)0.0462 (9)0.0322 (8)0.0034 (7)0.0015 (6)0.0037 (6)
C10.0377 (9)0.0382 (10)0.0282 (8)0.0057 (8)0.0030 (7)0.0058 (7)
C20.0434 (10)0.0536 (12)0.0324 (9)0.0077 (9)0.0012 (8)0.0031 (9)
C110.0385 (9)0.0495 (11)0.0327 (9)0.0021 (8)0.0003 (7)0.0019 (8)
C120.0467 (11)0.0610 (14)0.0360 (10)0.0087 (10)0.0041 (8)0.0044 (9)
C130.0541 (11)0.0646 (14)0.0305 (10)0.0024 (10)0.0036 (8)0.0002 (9)
C140.0408 (10)0.0543 (12)0.0397 (10)0.0023 (9)0.0067 (8)0.0055 (9)
C150.0407 (10)0.0498 (11)0.0422 (10)0.0049 (8)0.0039 (8)0.0029 (9)
C160.0454 (10)0.0566 (13)0.0310 (9)0.0034 (9)0.0004 (8)0.0020 (9)
C100.0491 (13)0.0735 (17)0.0613 (14)0.0129 (12)0.0017 (10)0.0118 (13)
Geometric parameters (Å, º) top
O1—C11.2420 (19)C2—H30.92 (2)
O17—C141.374 (2)C11—C121.386 (2)
O17—C101.423 (3)C11—C161.408 (3)
O18—C151.380 (2)C12—C131.393 (2)
O18—C101.429 (2)C12—H120.897 (18)
N1—C11.334 (2)C13—C141.358 (3)
N1—H1A0.90 (2)C13—H130.97 (2)
N1—H1B0.90 (2)C14—C151.380 (3)
N2—C11.362 (2)C15—C161.361 (2)
N2—N31.3794 (19)C16—H160.985 (18)
N2—H20.91 (2)C10—H10A0.95 (3)
N3—C21.274 (2)C10—H10B0.98 (2)
C2—C111.462 (2)
C14—O17—C10106.09 (15)C13—C12—H12119.2 (11)
C15—O18—C10105.81 (15)C14—C13—C12116.42 (17)
C1—N1—H1A118.3 (12)C14—C13—H13121.2 (11)
C1—N1—H1B117.4 (13)C12—C13—H13122.3 (11)
H1A—N1—H1B123.4 (19)C13—C14—O17127.90 (17)
C1—N2—N3120.17 (16)C13—C14—C15122.15 (16)
C1—N2—H2119.9 (11)O17—C14—C15109.94 (17)
N3—N2—H2119.0 (11)C16—C15—C14122.45 (18)
C2—N3—N2115.33 (15)C16—C15—O18127.85 (17)
O1—C1—N1123.62 (15)C14—C15—O18109.70 (15)
O1—C1—N2119.13 (16)C15—C16—C11116.78 (17)
N1—C1—N2117.23 (15)C15—C16—H16120.9 (10)
N3—C2—C11122.22 (18)C11—C16—H16122.3 (10)
N3—C2—H3121.5 (11)O17—C10—O18108.45 (16)
C11—C2—H3116.2 (11)O17—C10—H10A108.1 (15)
C12—C11—C16119.96 (16)O18—C10—H10A111.4 (14)
C12—C11—C2119.02 (17)O17—C10—H10B108.2 (14)
C16—C11—C2121.02 (15)O18—C10—H10B108.3 (13)
C11—C12—C13122.23 (19)H10A—C10—H10B112.3 (19)
C11—C12—H12118.5 (11)
C1—N2—N3—C2168.85 (16)C13—C14—C15—C161.0 (3)
N3—N2—C1—O1178.20 (14)O17—C14—C15—C16179.98 (18)
N3—N2—C1—N13.2 (2)C13—C14—C15—O18178.69 (18)
N2—N3—C2—C11178.32 (16)O17—C14—C15—O180.3 (2)
N3—C2—C11—C12171.77 (18)C10—O18—C15—C16179.4 (2)
N3—C2—C11—C169.2 (3)C10—O18—C15—C140.3 (2)
C16—C11—C12—C130.7 (3)C14—C15—C16—C110.4 (3)
C2—C11—C12—C13179.73 (18)O18—C15—C16—C11179.21 (19)
C11—C12—C13—C140.1 (3)C12—C11—C16—C150.4 (3)
C12—C13—C14—O17179.52 (19)C2—C11—C16—C15179.47 (18)
C12—C13—C14—C150.7 (3)C14—O17—C10—O180.9 (3)
C10—O17—C14—C13178.2 (2)C15—O18—C10—O170.7 (3)
C10—O17—C14—C150.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···N30.90 (2)2.27 (2)2.666 (2)106.2 (15)
N1—H1A···O1i0.90 (2)2.05 (2)2.922 (2)163.5 (17)
N2—H2···O1ii0.91 (2)2.01 (2)2.925 (2)175.9 (17)
Symmetry codes: (i) x+1, y1/2, z1/2; (ii) x+1, y+1, z.
 

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