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The non-H atoms of the title compound, C16H14N2O4, are essentially coplanar. An intra­molecular N—H...O hydrogen bond stabilizes the mol­ecular structure. Mol­ecules are linked via weak inter­molecular C—H...O hydrogen bonds, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056297/ci2264sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056297/ci2264Isup2.hkl
Contains datablock I

CCDC reference: 636206

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.102
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

2'-(1,3-Benzodioxol-5-ylmethylene)-2-methoxybenzohydrazide top
Crystal data top
C16H14N2O4F(000) = 624
Mr = 298.29Dx = 1.426 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 2965 reflections
a = 7.9913 (5) Åθ = 2.2–27.9°
b = 12.5941 (7) ŵ = 0.10 mm1
c = 14.1263 (10) ÅT = 113 K
β = 102.231 (3)°Prism, red
V = 1389.45 (15) Å30.22 × 0.20 × 0.16 mm
Z = 4
Data collection top
Rigaku SATURN
diffractometer
3307 independent reflections
Radiation source: rotating anode2725 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.2°
ω scansh = 109
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1616
Tmin = 0.977, Tmax = 0.984l = 1718
12843 measured reflections
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.054P)2 + 0.0088P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
3307 reflectionsΔρmax = 0.21 e Å3
205 parametersΔρmin = 0.17 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: 0.020 (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
O10.24637 (12)0.12309 (7)0.15772 (6)0.0359 (3)
O20.03951 (11)0.09135 (6)0.13865 (6)0.0264 (2)
O30.79610 (12)0.47073 (7)0.16752 (6)0.0321 (2)
O40.76055 (13)0.33881 (7)0.27636 (6)0.0406 (3)
N10.23485 (12)0.02093 (7)0.02473 (7)0.0214 (2)
H10.1882 (16)0.0119 (10)0.0380 (9)0.032*
N20.34765 (12)0.05358 (7)0.07401 (7)0.0214 (2)
C10.19222 (15)0.10811 (9)0.07090 (8)0.0223 (3)
C20.07635 (14)0.18709 (9)0.00980 (8)0.0220 (3)
C30.00776 (14)0.18127 (9)0.08986 (9)0.0223 (3)
C40.09051 (15)0.26471 (9)0.13752 (9)0.0282 (3)
H40.13530.26090.20530.034*
C50.12242 (17)0.35272 (10)0.08597 (10)0.0336 (3)
H50.18840.40950.11890.040*
C60.06023 (17)0.35945 (10)0.01227 (11)0.0337 (3)
H60.08470.41970.04740.040*
C70.03867 (15)0.27708 (9)0.05935 (10)0.0284 (3)
H70.08210.28190.12720.034*
C80.05242 (18)0.07713 (11)0.23636 (9)0.0348 (3)
H8A0.01530.13060.27790.052*
H8B0.02960.00600.25880.052*
H8C0.17540.08500.23930.052*
C90.37335 (14)0.13249 (9)0.02187 (8)0.0207 (3)
H90.31560.13420.04420.025*
C100.48754 (14)0.21991 (9)0.05956 (8)0.0199 (3)
C110.51267 (15)0.29855 (9)0.00515 (9)0.0241 (3)
H110.45700.29220.07140.029*
C120.61713 (15)0.38661 (9)0.02413 (9)0.0251 (3)
H120.63460.43990.02040.030*
C130.69273 (15)0.39187 (9)0.12024 (9)0.0228 (3)
C140.66945 (15)0.31357 (9)0.18525 (8)0.0237 (3)
C150.56800 (15)0.22688 (9)0.15825 (8)0.0229 (3)
H150.55250.17400.20360.028*
C160.85044 (17)0.43551 (10)0.26576 (9)0.0303 (3)
H16A0.82410.49020.31080.036*
H16B0.97550.42280.28090.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0427 (6)0.0354 (5)0.0241 (5)0.0102 (4)0.0055 (4)0.0078 (4)
O20.0297 (5)0.0281 (4)0.0195 (5)0.0038 (4)0.0013 (4)0.0001 (4)
O30.0376 (5)0.0271 (5)0.0304 (5)0.0126 (4)0.0050 (4)0.0024 (4)
O40.0532 (7)0.0387 (5)0.0239 (5)0.0233 (5)0.0052 (4)0.0009 (4)
N10.0223 (5)0.0214 (5)0.0187 (5)0.0026 (4)0.0001 (4)0.0012 (4)
N20.0197 (5)0.0206 (5)0.0227 (5)0.0009 (4)0.0015 (4)0.0029 (4)
C10.0208 (6)0.0222 (6)0.0233 (6)0.0011 (5)0.0030 (5)0.0011 (5)
C20.0185 (6)0.0222 (6)0.0254 (7)0.0013 (5)0.0052 (5)0.0007 (5)
C30.0197 (6)0.0215 (6)0.0270 (7)0.0012 (5)0.0076 (5)0.0030 (5)
C40.0240 (6)0.0289 (6)0.0320 (7)0.0006 (5)0.0067 (5)0.0098 (5)
C50.0274 (7)0.0252 (6)0.0496 (9)0.0072 (5)0.0111 (6)0.0116 (6)
C60.0310 (7)0.0229 (6)0.0500 (9)0.0040 (5)0.0150 (6)0.0011 (6)
C70.0249 (6)0.0258 (6)0.0353 (8)0.0009 (5)0.0078 (6)0.0033 (5)
C80.0386 (8)0.0438 (8)0.0195 (7)0.0036 (6)0.0008 (6)0.0002 (6)
C90.0212 (6)0.0228 (6)0.0179 (6)0.0011 (5)0.0033 (5)0.0023 (5)
C100.0187 (6)0.0197 (5)0.0216 (6)0.0025 (4)0.0053 (5)0.0008 (5)
C110.0254 (6)0.0269 (6)0.0191 (6)0.0008 (5)0.0028 (5)0.0015 (5)
C120.0280 (7)0.0229 (6)0.0253 (7)0.0000 (5)0.0077 (5)0.0045 (5)
C130.0212 (6)0.0207 (6)0.0271 (7)0.0020 (5)0.0060 (5)0.0031 (5)
C140.0249 (6)0.0255 (6)0.0190 (6)0.0005 (5)0.0010 (5)0.0007 (5)
C150.0253 (6)0.0217 (6)0.0217 (6)0.0010 (5)0.0046 (5)0.0016 (5)
C160.0312 (7)0.0303 (7)0.0279 (7)0.0085 (5)0.0028 (6)0.0059 (5)
Geometric parameters (Å, º) top
O1—C11.2257 (13)C6—C71.3858 (17)
O2—C31.3770 (14)C6—H60.95
O2—C81.4308 (14)C7—H70.95
O3—C131.3715 (13)C8—H8A0.98
O3—C161.4338 (14)C8—H8B0.98
O4—C141.3750 (14)C8—H8C0.98
O4—C161.4377 (14)C9—C101.4568 (15)
N1—C11.3568 (14)C9—H90.95
N1—N21.3827 (13)C10—C111.3909 (16)
N1—H10.893 (12)C10—C151.4089 (15)
N2—C91.2793 (14)C11—C121.3970 (16)
C1—C21.5010 (15)C11—H110.95
C2—C71.3979 (16)C12—C131.3657 (16)
C2—C31.4004 (16)C12—H120.95
C3—C41.3964 (16)C13—C141.3866 (16)
C4—C51.3794 (18)C14—C151.3652 (16)
C4—H40.95C15—H150.95
C5—C61.3741 (18)C16—H16A0.99
C5—H50.95C16—H16B0.99
C3—O2—C8118.32 (9)O2—C8—H8C109.5
C13—O3—C16105.96 (9)H8A—C8—H8C109.5
C14—O4—C16105.99 (9)H8B—C8—H8C109.5
C1—N1—N2120.70 (10)N2—C9—C10122.76 (11)
C1—N1—H1119.0 (9)N2—C9—H9118.6
N2—N1—H1120.3 (9)C10—C9—H9118.6
C9—N2—N1113.85 (10)C11—C10—C15120.45 (10)
O1—C1—N1122.29 (11)C11—C10—C9117.67 (11)
O1—C1—C2121.15 (10)C15—C10—C9121.87 (10)
N1—C1—C2116.55 (10)C10—C11—C12122.08 (11)
C7—C2—C3117.77 (11)C10—C11—H11119.0
C7—C2—C1114.92 (10)C12—C11—H11119.0
C3—C2—C1127.28 (10)C13—C12—C11116.33 (11)
O2—C3—C4121.47 (11)C13—C12—H12121.8
O2—C3—C2118.16 (10)C11—C12—H12121.8
C4—C3—C2120.37 (11)C12—C13—O3127.82 (10)
C5—C4—C3119.88 (12)C12—C13—C14122.05 (11)
C5—C4—H4120.1O3—C13—C14110.12 (10)
C3—C4—H4120.1C15—C14—O4127.72 (11)
C6—C5—C4121.00 (12)C15—C14—C13122.60 (11)
C6—C5—H5119.5O4—C14—C13109.68 (10)
C4—C5—H5119.5C14—C15—C10116.47 (10)
C5—C6—C7119.08 (12)C14—C15—H15121.8
C5—C6—H6120.5C10—C15—H15121.8
C7—C6—H6120.5O3—C16—O4107.90 (9)
C6—C7—C2121.87 (12)O3—C16—H16A110.1
C6—C7—H7119.1O4—C16—H16A110.1
C2—C7—H7119.1O3—C16—H16B110.1
O2—C8—H8A109.5O4—C16—H16B110.1
O2—C8—H8B109.5H16A—C16—H16B108.4
H8A—C8—H8B109.5
C1—N1—N2—C9178.70 (10)N2—C9—C10—C11176.60 (10)
N2—N1—C1—O12.36 (17)N2—C9—C10—C154.66 (17)
N2—N1—C1—C2176.78 (9)C15—C10—C11—C120.03 (18)
O1—C1—C2—C70.67 (16)C9—C10—C11—C12178.80 (10)
N1—C1—C2—C7178.48 (10)C10—C11—C12—C130.45 (17)
O1—C1—C2—C3178.78 (11)C11—C12—C13—O3177.98 (11)
N1—C1—C2—C30.37 (17)C11—C12—C13—C140.89 (18)
C8—O2—C3—C49.81 (16)C16—O3—C13—C12176.48 (12)
C8—O2—C3—C2169.92 (10)C16—O3—C13—C144.54 (13)
C7—C2—C3—O2177.88 (10)C16—O4—C14—C15178.09 (12)
C1—C2—C3—O24.05 (17)C16—O4—C14—C132.58 (13)
C7—C2—C3—C41.85 (16)C12—C13—C14—C150.94 (19)
C1—C2—C3—C4176.21 (11)O3—C13—C14—C15178.11 (10)
O2—C3—C4—C5178.76 (10)C12—C13—C14—O4179.69 (11)
C2—C3—C4—C50.97 (18)O3—C13—C14—O41.26 (14)
C3—C4—C5—C60.62 (19)O4—C14—C15—C10179.71 (11)
C4—C5—C6—C71.24 (19)C13—C14—C15—C100.47 (17)
C5—C6—C7—C20.28 (19)C11—C10—C15—C140.03 (16)
C3—C2—C7—C61.24 (18)C9—C10—C15—C14178.74 (10)
C1—C2—C7—C6177.06 (11)C13—O3—C16—O46.06 (13)
N1—N2—C9—C10179.98 (9)C14—O4—C16—O35.33 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.893 (12)1.928 (13)2.6502 (13)136.8 (12)
C4—H4···O1i0.952.453.2350 (15)140
C6—H6···O3ii0.952.533.4306 (17)160
C9—H9···O4iii0.952.503.4127 (14)161
C16—H16B···O1iv0.992.283.2587 (17)169
Symmetry codes: (i) x1/2, y1/2, z1/2; (ii) x1, y1, z; (iii) x1/2, y+1/2, z1/2; (iv) x+3/2, y+1/2, z+1/2.
 

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