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The title compound, C9H12N2O3, was synthesized by the reaction of ethyl 3,5-dimethoxy­benzoate with hydrazine. X-ray analysis reveals that the asymmetric unit contains two independent mol­ecules. N—H...O and C—H...O hydrogen bonds link the mol­ecules into layers. Mol­ecules in adjacent layers are linked via N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013511/ci2044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013511/ci2044Isup2.hkl
Contains datablock I

CCDC reference: 608392

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.071
  • wR factor = 0.172
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.89 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.13 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT414_ALERT_2_C Short Intra D-H..H-X H1 .. H7 .. 1.97 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H3 .. H16 .. 1.93 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4B ... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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, 1998); 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: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

3,5-Dimethoxybenzohydrazide top
Crystal data top
C9H12N2O3Z = 4
Mr = 196.21F(000) = 416
Triclinic, P1Dx = 1.395 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.705 (3) ÅCell parameters from 462 reflections
b = 10.082 (3) Åθ = 2.5–18.5°
c = 10.981 (3) ŵ = 0.11 mm1
α = 104.222 (2)°T = 298 K
β = 90.735 (3)°Block, colourless
γ = 90.916 (3)°0.49 × 0.17 × 0.15 mm
V = 933.9 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3217 independent reflections
Radiation source: fine-focus sealed tube1120 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.950, Tmax = 0.984k = 1111
4831 measured reflectionsl = 913
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0427P)2]
where P = (Fo2 + 2Fc2)/3
3217 reflections(Δ/σ)max = 0.002
269 parametersΔρmax = 0.27 e Å3
6 restraintsΔρmin = 0.26 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
N10.2238 (5)0.6328 (4)0.4802 (4)0.0481 (13)
H10.25500.71650.49310.058*
N20.1135 (6)0.5837 (5)0.3834 (6)0.0582 (17)
H2A0.141 (7)0.505 (4)0.347 (5)0.080*
H2B0.024 (4)0.584 (7)0.414 (6)0.080*
N30.7028 (5)0.8502 (4)0.4612 (4)0.0415 (13)
H30.73070.77370.47510.050*
N40.5922 (6)0.8478 (5)0.3657 (5)0.0523 (15)
H4A0.503 (4)0.861 (7)0.396 (6)0.080*
H4B0.638 (6)0.878 (6)0.312 (5)0.080*
O10.2374 (4)0.4367 (4)0.5388 (3)0.0557 (12)
O20.6534 (4)0.5288 (4)0.8827 (4)0.0655 (13)
O30.5499 (4)0.9591 (3)0.8004 (3)0.0571 (12)
O40.7264 (4)1.0788 (3)0.5166 (3)0.0543 (12)
O51.1439 (4)1.1749 (4)0.8587 (3)0.0565 (12)
O61.0307 (5)0.7005 (3)0.7742 (4)0.0592 (12)
C10.2820 (6)0.5578 (6)0.5524 (5)0.0388 (15)
C20.3951 (6)0.6226 (5)0.6515 (5)0.0385 (15)
C30.4698 (6)0.5401 (5)0.7170 (5)0.0422 (16)
H3A0.44950.44630.69740.051*
C40.5720 (6)0.5969 (6)0.8094 (5)0.0444 (16)
C50.6053 (6)0.7391 (6)0.8423 (5)0.0493 (17)
H50.67600.77740.90590.059*
C60.5299 (6)0.8174 (5)0.7773 (5)0.0423 (16)
C70.4273 (6)0.7628 (5)0.6817 (5)0.0411 (16)
H70.37960.81880.63750.049*
C80.6229 (7)0.3851 (6)0.8594 (6)0.073 (2)
H8A0.68220.34820.91720.110*
H8B0.65050.34130.77490.110*
H8C0.51560.36920.87040.110*
C90.6568 (7)1.0227 (5)0.8972 (5)0.0572 (18)
H9A0.65971.11960.90480.086*
H9B0.75700.98640.87660.086*
H9C0.62561.00500.97530.086*
C100.7658 (6)0.9654 (5)0.5309 (5)0.0363 (14)
C110.8815 (6)0.9556 (5)0.6274 (5)0.0346 (14)
C120.9594 (6)1.0744 (5)0.6926 (5)0.0398 (15)
H120.94161.15770.67330.048*
C131.0620 (6)1.0660 (5)0.7847 (5)0.0401 (15)
C141.0902 (6)0.9426 (5)0.8168 (5)0.0444 (16)
H141.15950.93930.88110.053*
C151.0139 (7)0.8271 (5)0.7515 (5)0.0444 (16)
C160.9092 (6)0.8307 (5)0.6570 (5)0.0424 (16)
H160.85780.75130.61350.051*
C171.1239 (6)1.3081 (5)0.8366 (5)0.0569 (18)
H17A1.18481.37410.89650.085*
H17B1.01761.33180.84540.085*
H17C1.15611.30740.75310.085*
C181.1140 (7)0.6947 (6)0.8844 (5)0.063 (2)
H18A1.11080.60270.89430.095*
H18B1.06880.75480.95600.095*
H18C1.21880.72270.87750.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.063 (3)0.026 (3)0.057 (3)0.008 (2)0.024 (3)0.014 (2)
N20.073 (4)0.040 (3)0.063 (4)0.003 (4)0.021 (4)0.016 (3)
N30.056 (3)0.020 (3)0.048 (3)0.002 (2)0.020 (3)0.009 (2)
N40.056 (4)0.040 (3)0.061 (4)0.011 (3)0.011 (3)0.013 (3)
O10.074 (3)0.021 (2)0.071 (3)0.015 (2)0.024 (2)0.011 (2)
O20.080 (3)0.035 (3)0.086 (3)0.012 (2)0.038 (3)0.027 (2)
O30.080 (3)0.025 (2)0.065 (3)0.015 (2)0.029 (2)0.011 (2)
O40.077 (3)0.021 (2)0.066 (3)0.000 (2)0.017 (2)0.014 (2)
O50.069 (3)0.028 (2)0.068 (3)0.010 (2)0.024 (2)0.005 (2)
O60.096 (3)0.018 (2)0.066 (3)0.004 (2)0.026 (2)0.016 (2)
C10.046 (4)0.030 (4)0.039 (4)0.002 (3)0.005 (3)0.006 (3)
C20.048 (4)0.030 (3)0.040 (4)0.009 (3)0.010 (3)0.014 (3)
C30.054 (4)0.026 (3)0.048 (4)0.001 (3)0.009 (3)0.014 (3)
C40.052 (4)0.034 (4)0.049 (4)0.004 (3)0.017 (3)0.015 (3)
C50.057 (4)0.035 (4)0.053 (4)0.009 (3)0.009 (3)0.008 (3)
C60.057 (4)0.019 (3)0.053 (4)0.009 (3)0.013 (3)0.014 (3)
C70.055 (4)0.029 (4)0.041 (4)0.005 (3)0.015 (3)0.014 (3)
C80.103 (6)0.040 (4)0.082 (5)0.002 (4)0.024 (4)0.026 (4)
C90.074 (5)0.034 (4)0.055 (4)0.013 (3)0.018 (4)0.003 (3)
C100.045 (4)0.020 (3)0.044 (4)0.006 (3)0.000 (3)0.008 (3)
C110.046 (4)0.022 (3)0.037 (4)0.000 (3)0.009 (3)0.010 (3)
C120.053 (4)0.024 (3)0.044 (4)0.002 (3)0.002 (3)0.011 (3)
C130.045 (4)0.029 (4)0.046 (4)0.004 (3)0.007 (3)0.008 (3)
C140.051 (4)0.027 (4)0.055 (4)0.003 (3)0.010 (3)0.009 (3)
C150.064 (4)0.020 (4)0.050 (4)0.006 (3)0.006 (3)0.010 (3)
C160.062 (4)0.014 (3)0.047 (4)0.008 (3)0.008 (3)0.001 (3)
C170.075 (5)0.017 (3)0.078 (5)0.007 (3)0.009 (4)0.010 (3)
C180.105 (6)0.037 (4)0.050 (4)0.002 (4)0.014 (4)0.016 (3)
Geometric parameters (Å, º) top
N1—C11.324 (6)C5—C61.358 (6)
N1—N21.413 (7)C5—H50.93
N1—H10.86C6—C71.370 (7)
N2—H2A0.84 (3)C7—H70.93
N2—H2B0.85 (3)C8—H8A0.96
N3—C101.329 (6)C8—H8B0.96
N3—N41.411 (6)C8—H8C0.96
N3—H30.86C9—H9A0.96
N4—H4A0.84 (3)C9—H9B0.96
N4—H4B0.84 (3)C9—H9C0.96
O1—C11.248 (6)C10—C111.475 (6)
O2—C41.376 (5)C11—C121.395 (7)
O2—C81.428 (6)C11—C161.399 (6)
O3—C61.396 (6)C12—C131.360 (6)
O3—C91.423 (6)C12—H120.93
O4—C101.245 (5)C13—C141.398 (6)
O5—C131.376 (6)C14—C151.366 (7)
O5—C171.435 (5)C14—H140.93
O6—C151.368 (6)C15—C161.381 (6)
O6—C181.416 (5)C16—H160.93
C1—C21.478 (7)C17—H17A0.96
C2—C31.390 (6)C17—H17B0.96
C2—C71.392 (7)C17—H17C0.96
C3—C41.350 (7)C18—H18A0.96
C3—H3A0.93C18—H18B0.96
C4—C51.414 (7)C18—H18C0.96
C1—N1—N2124.0 (5)H8A—C8—H8C109.5
C1—N1—H1118.0H8B—C8—H8C109.5
N2—N1—H1118.0O3—C9—H9A109.5
N1—N2—H2A106 (4)O3—C9—H9B109.5
N1—N2—H2B110 (5)H9A—C9—H9B109.5
H2A—N2—H2B113 (7)O3—C9—H9C109.5
C10—N3—N4123.0 (4)H9A—C9—H9C109.5
C10—N3—H3118.5H9B—C9—H9C109.5
N4—N3—H3118.5O4—C10—N3120.9 (5)
N3—N4—H4A111 (4)O4—C10—C11120.8 (5)
N3—N4—H4B105 (4)N3—C10—C11118.3 (5)
H4A—N4—H4B133 (6)C12—C11—C16120.2 (5)
C4—O2—C8116.1 (4)C12—C11—C10118.8 (5)
C6—O3—C9117.2 (4)C16—C11—C10120.9 (5)
C13—O5—C17118.5 (4)C13—C12—C11118.7 (5)
C15—O6—C18116.8 (4)C13—C12—H12120.6
O1—C1—N1120.1 (5)C11—C12—H12120.6
O1—C1—C2121.4 (5)C12—C13—O5125.1 (5)
N1—C1—C2118.4 (5)C12—C13—C14122.0 (5)
C3—C2—C7119.5 (5)O5—C13—C14112.8 (5)
C3—C2—C1118.3 (5)C15—C14—C13118.6 (5)
C7—C2—C1122.2 (5)C15—C14—H14120.7
C4—C3—C2119.6 (5)C13—C14—H14120.7
C4—C3—H3A120.2C14—C15—O6124.2 (5)
C2—C3—H3A120.2C14—C15—C16121.4 (5)
C3—C4—O2126.1 (5)O6—C15—C16114.4 (5)
C3—C4—C5121.8 (5)C15—C16—C11119.1 (5)
O2—C4—C5112.1 (5)C15—C16—H16120.5
C6—C5—C4117.4 (5)C11—C16—H16120.5
C6—C5—H5121.3O5—C17—H17A109.5
C4—C5—H5121.3O5—C17—H17B109.5
C5—C6—C7122.3 (5)H17A—C17—H17B109.5
C5—C6—O3123.6 (5)O5—C17—H17C109.5
C7—C6—O3114.0 (4)H17A—C17—H17C109.5
C6—C7—C2119.4 (5)H17B—C17—H17C109.5
C6—C7—H7120.3O6—C18—H18A109.5
C2—C7—H7120.3O6—C18—H18B109.5
O2—C8—H8A109.5H18A—C18—H18B109.5
O2—C8—H8B109.5O6—C18—H18C109.5
H8A—C8—H8B109.5H18A—C18—H18C109.5
O2—C8—H8C109.5H18B—C18—H18C109.5
N2—N1—C1—O11.6 (8)N4—N3—C10—O41.7 (8)
N2—N1—C1—C2179.2 (5)N4—N3—C10—C11179.4 (5)
O1—C1—C2—C310.1 (8)O4—C10—C11—C127.4 (8)
N1—C1—C2—C3172.4 (5)N3—C10—C11—C12173.7 (5)
O1—C1—C2—C7169.2 (5)O4—C10—C11—C16170.2 (5)
N1—C1—C2—C78.4 (8)N3—C10—C11—C168.6 (8)
C7—C2—C3—C40.3 (8)C16—C11—C12—C130.0 (8)
C1—C2—C3—C4179.0 (5)C10—C11—C12—C13177.6 (5)
C2—C3—C4—O2179.4 (5)C11—C12—C13—O5178.2 (5)
C2—C3—C4—C50.3 (9)C11—C12—C13—C140.7 (8)
C8—O2—C4—C31.5 (8)C17—O5—C13—C121.5 (8)
C8—O2—C4—C5177.8 (5)C17—O5—C13—C14179.2 (5)
C3—C4—C5—C60.2 (9)C12—C13—C14—C151.2 (8)
O2—C4—C5—C6179.1 (5)O5—C13—C14—C15179.0 (5)
C4—C5—C6—C71.2 (8)C13—C14—C15—O6179.6 (5)
C4—C5—C6—O3179.3 (5)C13—C14—C15—C160.9 (9)
C9—O3—C6—C50.5 (8)C18—O6—C15—C1410.2 (8)
C9—O3—C6—C7179.0 (5)C18—O6—C15—C16168.6 (5)
C5—C6—C7—C21.8 (9)C14—C15—C16—C110.2 (8)
O3—C6—C7—C2178.7 (5)O6—C15—C16—C11179.1 (5)
C3—C2—C7—C61.3 (8)C12—C11—C16—C150.3 (8)
C1—C2—C7—C6178.0 (5)C10—C11—C16—C15177.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.862.102.925 (5)162
N2—H2B···O1ii0.85 (4)2.36 (4)3.199 (6)170 (6)
N3—H3···O1iii0.862.112.947 (6)164
N4—H4A···O4i0.85 (4)2.25 (4)3.098 (6)174 (4)
C7—H7···O4i0.932.373.284 (6)167
C16—H16···O1iii0.932.333.239 (7)165
C9—H9B···Cg0.962.613.462 (6)148
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z+1.
 

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