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The mol­ecules of the title compound, C16H16N2O4, are linked by hydrogen bonds into a zigzag chain running along the c axis of the monoclinic cell.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007154/bt6616sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007154/bt6616Isup2.hkl
Contains datablock I

CCDC reference: 270237

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.124
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C13 .. 5.15 su
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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

5-Methoxysalicylaldehyde 3-methoxybenzoylhydrazone top
Crystal data top
C16H16N2O4F(000) = 632
Mr = 300.31Dx = 1.360 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3157 reflections
a = 6.4024 (4) Åθ = 2.6–27.1°
b = 31.441 (2) ŵ = 0.10 mm1
c = 7.3660 (5) ÅT = 295 K
β = 98.330 (1)°Prism, yellow
V = 1467.1 (2) Å30.48 × 0.32 × 0.21 mm
Z = 4
Data collection top
Bruker SMART area-detector
diffractometer
2285 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 27.1°, θmin = 2.6°
φ and ω scansh = 86
7971 measured reflectionsk = 2540
3190 independent reflectionsl = 89
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124All H-atom parameters refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0681P)2 + 0.1473P]
where P = (Fo2 + 2Fc2)/3
3190 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.16 e Å3
16 restraintsΔρmin = 0.20 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.0044 (2)0.18295 (4)0.5314 (2)0.0648 (3)
O20.7205 (2)0.02140 (4)0.3347 (2)0.0765 (4)
O30.6585 (2)0.28568 (3)0.6127 (2)0.0588 (3)
O40.3017 (2)0.42824 (4)0.4125 (2)0.0765 (4)
N10.6144 (2)0.20983 (4)0.4436 (2)0.0488 (3)
N20.4638 (2)0.24125 (4)0.4149 (2)0.0510 (3)
C10.9241 (2)0.14433 (5)0.4768 (2)0.0497 (4)
C21.0589 (3)0.10958 (6)0.4943 (2)0.0614 (4)
C30.9866 (3)0.06952 (6)0.4477 (2)0.0648 (5)
C40.7768 (3)0.06273 (5)0.3778 (2)0.0555 (4)
C50.6413 (2)0.09705 (5)0.3550 (2)0.0498 (4)
C60.7117 (2)0.13811 (4)0.4046 (2)0.0442 (3)
C70.5111 (4)0.01374 (7)0.2554 (4)0.0895 (7)
C80.5615 (2)0.17294 (4)0.3807 (2)0.0467 (3)
C90.4986 (2)0.27863 (4)0.5040 (2)0.0441 (3)
C100.3317 (2)0.31144 (4)0.4574 (2)0.0436 (3)
C110.1215 (2)0.30132 (6)0.4051 (2)0.0547 (4)
C120.0223 (3)0.33408 (7)0.3587 (2)0.0653 (5)
C130.0438 (3)0.37555 (6)0.3632 (2)0.0644 (5)
C140.2526 (3)0.38563 (5)0.4153 (2)0.0543 (4)
C150.3974 (2)0.35367 (5)0.4658 (2)0.0474 (3)
C160.5174 (4)0.43989 (6)0.4489 (4)0.0818 (6)
H1o0.898 (3)0.1999 (6)0.512 (3)0.106 (8)*
H2n0.357 (2)0.2367 (5)0.333 (2)0.065 (5)*
H21.203 (2)0.1142 (6)0.542 (2)0.068 (5)*
H31.074 (3)0.0452 (4)0.460 (2)0.077 (6)*
H50.496 (2)0.0929 (5)0.304 (2)0.050 (4)*
H80.424 (2)0.1671 (5)0.321 (2)0.061 (5)*
H120.164 (2)0.3256 (5)0.324 (2)0.070 (5)*
H130.055 (2)0.3975 (5)0.329 (2)0.078 (5)*
H150.543 (2)0.3594 (5)0.505 (2)0.054 (4)*
H710.420 (3)0.0207 (8)0.344 (3)0.112 (8)*
H720.507 (4)0.0162 (3)0.236 (3)0.106 (7)*
H730.477 (4)0.0290 (7)0.142 (2)0.107 (8)*
H110.073 (2)0.2731 (3)0.403 (2)0.056 (4)*
H1610.521 (4)0.4692 (4)0.409 (3)0.121 (8)*
H1620.566 (4)0.4343 (8)0.578 (2)0.113 (9)*
H1630.592 (3)0.4240 (6)0.366 (3)0.105 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.053 (1)0.061 (1)0.075 (1)0.006 (1)0.008 (1)0.002 (1)
O20.080 (1)0.042 (1)0.106 (1)0.012 (1)0.007 (1)0.004 (1)
O30.058 (1)0.043 (1)0.066 (1)0.002 (1)0.024 (1)0.002 (1)
O40.088 (1)0.042 (1)0.099 (1)0.021 (1)0.011 (1)0.000 (1)
N10.050 (1)0.040 (1)0.052 (1)0.006 (1)0.009 (1)0.002 (1)
N20.048 (1)0.038 (1)0.061 (1)0.005 (1)0.017 (1)0.003 (1)
C10.049 (1)0.052 (1)0.046 (1)0.001 (1)0.001 (1)0.004 (1)
C20.045 (1)0.069 (1)0.067 (1)0.011 (1)0.001 (1)0.003 (1)
C30.061 (1)0.062 (1)0.071 (1)0.025 (1)0.007 (1)0.005 (1)
C40.063 (1)0.042 (1)0.061 (1)0.010 (1)0.009 (1)0.001 (1)
C50.051 (1)0.044 (1)0.054 (1)0.005 (1)0.002 (1)0.001 (1)
C60.048 (1)0.042 (1)0.041 (1)0.005 (1)0.001 (1)0.004 (1)
C70.099 (2)0.040 (1)0.117 (2)0.004 (1)0.005 (2)0.016 (1)
C80.047 (1)0.040 (1)0.049 (1)0.001 (1)0.004 (1)0.002 (1)
C90.044 (1)0.039 (1)0.046 (1)0.002 (1)0.006 (1)0.003 (1)
C100.044 (1)0.044 (1)0.041 (1)0.004 (1)0.001 (1)0.001 (1)
C110.046 (1)0.057 (1)0.059 (1)0.001 (1)0.002 (1)0.002 (1)
C120.040 (1)0.087 (1)0.068 (1)0.010 (1)0.003 (1)0.001 (1)
C130.057 (1)0.067 (1)0.068 (1)0.026 (1)0.006 (1)0.001 (1)
C140.061 (1)0.049 (1)0.052 (1)0.016 (1)0.007 (1)0.002 (1)
C150.046 (1)0.045 (1)0.049 (1)0.007 (1)0.000 (1)0.004 (1)
C160.093 (2)0.046 (1)0.109 (2)0.002 (1)0.020 (1)0.008 (1)
Geometric parameters (Å, º) top
O1—C11.357 (2)C12—C131.370 (3)
O2—C41.373 (2)C13—C141.374 (2)
O2—C71.403 (3)C14—C151.381 (2)
O3—C91.225 (2)O1—H1o0.86 (1)
O4—C141.377 (2)N2—H2n0.86 (1)
O4—C161.416 (3)C2—H20.95 (1)
N1—C81.276 (2)C3—H30.94 (1)
N1—N21.375 (2)C5—H50.96 (1)
N2—C91.349 (2)C7—H710.96 (1)
C1—C21.387 (2)C7—H720.95 (1)
C1—C61.400 (2)C7—H730.96 (1)
C2—C31.369 (3)C8—H80.94 (1)
C3—C41.384 (3)C11—H110.94 (1)
C4—C51.380 (2)C12—H120.94 (1)
C5—C61.398 (2)C13—H130.95 (1)
C6—C81.452 (2)C15—H150.95 (1)
C9—C101.489 (2)C16—H1610.97 (1)
C10—C111.382 (2)C16—H1620.97 (1)
C10—C151.391 (2)C16—H1630.97 (1)
C11—C121.391 (2)
C4—O2—C7117.5 (1)C9—N2—H2n123 (1)
C14—O4—C16117.9 (1)N1—N2—H2n117 (1)
C8—N1—N2117.0 (1)C3—C2—H2121 (1)
C9—N2—N1119.2 (1)C1—C2—H2118 (1)
O1—C1—C2118.3 (1)C2—C3—H3123 (1)
O1—C1—C6122.9 (1)C4—C3—H3116 (1)
C2—C1—C6118.8 (2)C4—C5—H5120 (1)
C3—C2—C1121.2 (2)C6—C5—H5119 (1)
C2—C3—C4120.7 (2)O2—C7—H71109 (2)
O2—C4—C5124.9 (2)O2—C7—H72104 (2)
O2—C4—C3116.1 (1)H71—C7—H72109 (2)
C5—C4—C3119.0 (2)O2—C7—H73111 (2)
C4—C5—C6121.1 (2)H71—C7—H73113 (2)
C5—C6—C1119.1 (1)H72—C7—H73112 (2)
C5—C6—C8118.8 (1)N1—C8—H8122 (1)
C1—C6—C8122.1 (1)C6—C8—H8118 (1)
N1—C8—C6120.3 (1)C10—C11—H11122 (1)
O3—C9—N2122.6 (1)C12—C11—H11119 (1)
O3—C9—C10122.0 (1)C13—C12—H12124 (1)
N2—C9—C10115.4 (1)C11—C12—H12116 (1)
C11—C10—C15120.5 (1)C12—C13—H13120 (1)
C11—C10—C9122.8 (1)C14—C13—H13120 (1)
C15—C10—C9116.6 (1)C14—C15—H15122 (1)
C10—C11—C12118.8 (2)C10—C15—H15118 (1)
C13—C12—C11120.5 (2)O4—C16—H161105 (2)
C12—C13—C14120.7 (2)O4—C16—H162108 (2)
C13—C14—O4115.8 (1)H161—C16—H162117 (2)
C13—C14—C15119.7 (2)O4—C16—H163108 (1)
O4—C14—C15124.5 (2)H161—C16—H163105 (2)
C14—C15—C10119.7 (1)H162—C16—H163114 (2)
C1—O1—H1o104 (2)
C8—N1—N2—C9169.0 (1)N1—N2—C9—O31.3 (2)
O1—C1—C2—C3177.8 (2)N1—N2—C9—C10177.1 (1)
C6—C1—C2—C32.0 (2)O3—C9—C10—C11151.1 (2)
C1—C2—C3—C41.4 (3)N2—C9—C10—C1130.5 (2)
C7—O2—C4—C52.4 (3)O3—C9—C10—C1529.9 (2)
C7—O2—C4—C3177.1 (2)N2—C9—C10—C15148.5 (1)
C2—C3—C4—O2179.8 (2)C15—C10—C11—C120.9 (2)
C2—C3—C4—C50.2 (3)C9—C10—C11—C12178.1 (1)
O2—C4—C5—C6179.2 (1)C10—C11—C12—C130.6 (3)
C3—C4—C5—C61.3 (2)C11—C12—C13—C140.6 (3)
C4—C5—C6—C10.7 (2)C12—C13—C14—O4179.2 (2)
C4—C5—C6—C8178.9 (1)C12—C13—C14—C150.8 (2)
O1—C1—C6—C5178.8 (1)C16—O4—C14—C13174.4 (2)
C2—C1—C6—C51.0 (2)C16—O4—C14—C155.5 (2)
O1—C1—C6—C80.8 (2)C13—C14—C15—C102.2 (2)
C2—C1—C6—C8179.5 (1)O4—C14—C15—C10177.7 (1)
N2—N1—C8—C6179.7 (1)C11—C10—C15—C142.2 (2)
C5—C6—C8—N1172.0 (1)C9—C10—C15—C14176.7 (1)
C1—C6—C8—N17.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.86 (1)1.84 (1)2.626 (2)151 (2)
N2—H2n···O3i0.86 (1)2.04 (1)2.869 (2)164 (2)
Symmetry code: (i) x1/2, y+1/2, z1/2.
 

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