organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007154/bt6616sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007154/bt6616Isup2.hkl |
CCDC reference: 270237
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
C16H16N2O4 | F(000) = 632 |
Mr = 300.31 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3157 reflections |
a = 6.4024 (4) Å | θ = 2.6–27.1° |
b = 31.441 (2) Å | µ = 0.10 mm−1 |
c = 7.3660 (5) Å | T = 295 K |
β = 98.330 (1)° | Prism, yellow |
V = 1467.1 (2) Å3 | 0.48 × 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 tube | Rint = 0.016 |
Graphite monochromator | θmax = 27.1°, θmin = 2.6° |
φ and ω scans | h = −8→6 |
7971 measured reflections | k = −25→40 |
3190 independent reflections | l = −8→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | All 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 parameters | Δρmax = 0.16 e Å−3 |
16 restraints | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 1.0044 (2) | 0.18295 (4) | 0.5314 (2) | 0.0648 (3) | |
O2 | 0.7205 (2) | 0.02140 (4) | 0.3347 (2) | 0.0765 (4) | |
O3 | 0.6585 (2) | 0.28568 (3) | 0.6127 (2) | 0.0588 (3) | |
O4 | 0.3017 (2) | 0.42824 (4) | 0.4125 (2) | 0.0765 (4) | |
N1 | 0.6144 (2) | 0.20983 (4) | 0.4436 (2) | 0.0488 (3) | |
N2 | 0.4638 (2) | 0.24125 (4) | 0.4149 (2) | 0.0510 (3) | |
C1 | 0.9241 (2) | 0.14433 (5) | 0.4768 (2) | 0.0497 (4) | |
C2 | 1.0589 (3) | 0.10958 (6) | 0.4943 (2) | 0.0614 (4) | |
C3 | 0.9866 (3) | 0.06952 (6) | 0.4477 (2) | 0.0648 (5) | |
C4 | 0.7768 (3) | 0.06273 (5) | 0.3778 (2) | 0.0555 (4) | |
C5 | 0.6413 (2) | 0.09705 (5) | 0.3550 (2) | 0.0498 (4) | |
C6 | 0.7117 (2) | 0.13811 (4) | 0.4046 (2) | 0.0442 (3) | |
C7 | 0.5111 (4) | 0.01374 (7) | 0.2554 (4) | 0.0895 (7) | |
C8 | 0.5615 (2) | 0.17294 (4) | 0.3807 (2) | 0.0467 (3) | |
C9 | 0.4986 (2) | 0.27863 (4) | 0.5040 (2) | 0.0441 (3) | |
C10 | 0.3317 (2) | 0.31144 (4) | 0.4574 (2) | 0.0436 (3) | |
C11 | 0.1215 (2) | 0.30132 (6) | 0.4051 (2) | 0.0547 (4) | |
C12 | −0.0223 (3) | 0.33408 (7) | 0.3587 (2) | 0.0653 (5) | |
C13 | 0.0438 (3) | 0.37555 (6) | 0.3632 (2) | 0.0644 (5) | |
C14 | 0.2526 (3) | 0.38563 (5) | 0.4153 (2) | 0.0543 (4) | |
C15 | 0.3974 (2) | 0.35367 (5) | 0.4658 (2) | 0.0474 (3) | |
C16 | 0.5174 (4) | 0.43989 (6) | 0.4489 (4) | 0.0818 (6) | |
H1o | 0.898 (3) | 0.1999 (6) | 0.512 (3) | 0.106 (8)* | |
H2n | 0.357 (2) | 0.2367 (5) | 0.333 (2) | 0.065 (5)* | |
H2 | 1.203 (2) | 0.1142 (6) | 0.542 (2) | 0.068 (5)* | |
H3 | 1.074 (3) | 0.0452 (4) | 0.460 (2) | 0.077 (6)* | |
H5 | 0.496 (2) | 0.0929 (5) | 0.304 (2) | 0.050 (4)* | |
H8 | 0.424 (2) | 0.1671 (5) | 0.321 (2) | 0.061 (5)* | |
H12 | −0.164 (2) | 0.3256 (5) | 0.324 (2) | 0.070 (5)* | |
H13 | −0.055 (2) | 0.3975 (5) | 0.329 (2) | 0.078 (5)* | |
H15 | 0.543 (2) | 0.3594 (5) | 0.505 (2) | 0.054 (4)* | |
H71 | 0.420 (3) | 0.0207 (8) | 0.344 (3) | 0.112 (8)* | |
H72 | 0.507 (4) | −0.0162 (3) | 0.236 (3) | 0.106 (7)* | |
H73 | 0.477 (4) | 0.0290 (7) | 0.142 (2) | 0.107 (8)* | |
H11 | 0.073 (2) | 0.2731 (3) | 0.403 (2) | 0.056 (4)* | |
H161 | 0.521 (4) | 0.4692 (4) | 0.409 (3) | 0.121 (8)* | |
H162 | 0.566 (4) | 0.4343 (8) | 0.578 (2) | 0.113 (9)* | |
H163 | 0.592 (3) | 0.4240 (6) | 0.366 (3) | 0.105 (8)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.053 (1) | 0.061 (1) | 0.075 (1) | −0.006 (1) | −0.008 (1) | −0.002 (1) |
O2 | 0.080 (1) | 0.042 (1) | 0.106 (1) | 0.012 (1) | 0.007 (1) | −0.004 (1) |
O3 | 0.058 (1) | 0.043 (1) | 0.066 (1) | 0.002 (1) | −0.024 (1) | −0.002 (1) |
O4 | 0.088 (1) | 0.042 (1) | 0.099 (1) | 0.021 (1) | 0.011 (1) | 0.000 (1) |
N1 | 0.050 (1) | 0.040 (1) | 0.052 (1) | 0.006 (1) | −0.009 (1) | 0.002 (1) |
N2 | 0.048 (1) | 0.038 (1) | 0.061 (1) | 0.005 (1) | −0.017 (1) | −0.003 (1) |
C1 | 0.049 (1) | 0.052 (1) | 0.046 (1) | 0.001 (1) | 0.001 (1) | 0.004 (1) |
C2 | 0.045 (1) | 0.069 (1) | 0.067 (1) | 0.011 (1) | −0.001 (1) | 0.003 (1) |
C3 | 0.061 (1) | 0.062 (1) | 0.071 (1) | 0.025 (1) | 0.007 (1) | 0.005 (1) |
C4 | 0.063 (1) | 0.042 (1) | 0.061 (1) | 0.010 (1) | 0.009 (1) | 0.001 (1) |
C5 | 0.051 (1) | 0.044 (1) | 0.054 (1) | 0.005 (1) | 0.002 (1) | 0.001 (1) |
C6 | 0.048 (1) | 0.042 (1) | 0.041 (1) | 0.005 (1) | 0.001 (1) | 0.004 (1) |
C7 | 0.099 (2) | 0.040 (1) | 0.117 (2) | −0.004 (1) | 0.005 (2) | −0.016 (1) |
C8 | 0.047 (1) | 0.040 (1) | 0.049 (1) | 0.001 (1) | −0.004 (1) | 0.002 (1) |
C9 | 0.044 (1) | 0.039 (1) | 0.046 (1) | −0.002 (1) | −0.006 (1) | 0.003 (1) |
C10 | 0.044 (1) | 0.044 (1) | 0.041 (1) | 0.004 (1) | −0.001 (1) | −0.001 (1) |
C11 | 0.046 (1) | 0.057 (1) | 0.059 (1) | −0.001 (1) | 0.002 (1) | −0.002 (1) |
C12 | 0.040 (1) | 0.087 (1) | 0.068 (1) | 0.010 (1) | 0.003 (1) | −0.001 (1) |
C13 | 0.057 (1) | 0.067 (1) | 0.068 (1) | 0.026 (1) | 0.006 (1) | 0.001 (1) |
C14 | 0.061 (1) | 0.049 (1) | 0.052 (1) | 0.016 (1) | 0.007 (1) | −0.002 (1) |
C15 | 0.046 (1) | 0.045 (1) | 0.049 (1) | 0.007 (1) | 0.000 (1) | −0.004 (1) |
C16 | 0.093 (2) | 0.046 (1) | 0.109 (2) | −0.002 (1) | 0.020 (1) | −0.008 (1) |
Geometric parameters (Å, º) top
O1—C1 | 1.357 (2) | C12—C13 | 1.370 (3) |
O2—C4 | 1.373 (2) | C13—C14 | 1.374 (2) |
O2—C7 | 1.403 (3) | C14—C15 | 1.381 (2) |
O3—C9 | 1.225 (2) | O1—H1o | 0.86 (1) |
O4—C14 | 1.377 (2) | N2—H2n | 0.86 (1) |
O4—C16 | 1.416 (3) | C2—H2 | 0.95 (1) |
N1—C8 | 1.276 (2) | C3—H3 | 0.94 (1) |
N1—N2 | 1.375 (2) | C5—H5 | 0.96 (1) |
N2—C9 | 1.349 (2) | C7—H71 | 0.96 (1) |
C1—C2 | 1.387 (2) | C7—H72 | 0.95 (1) |
C1—C6 | 1.400 (2) | C7—H73 | 0.96 (1) |
C2—C3 | 1.369 (3) | C8—H8 | 0.94 (1) |
C3—C4 | 1.384 (3) | C11—H11 | 0.94 (1) |
C4—C5 | 1.380 (2) | C12—H12 | 0.94 (1) |
C5—C6 | 1.398 (2) | C13—H13 | 0.95 (1) |
C6—C8 | 1.452 (2) | C15—H15 | 0.95 (1) |
C9—C10 | 1.489 (2) | C16—H161 | 0.97 (1) |
C10—C11 | 1.382 (2) | C16—H162 | 0.97 (1) |
C10—C15 | 1.391 (2) | C16—H163 | 0.97 (1) |
C11—C12 | 1.391 (2) | ||
C4—O2—C7 | 117.5 (1) | C9—N2—H2n | 123 (1) |
C14—O4—C16 | 117.9 (1) | N1—N2—H2n | 117 (1) |
C8—N1—N2 | 117.0 (1) | C3—C2—H2 | 121 (1) |
C9—N2—N1 | 119.2 (1) | C1—C2—H2 | 118 (1) |
O1—C1—C2 | 118.3 (1) | C2—C3—H3 | 123 (1) |
O1—C1—C6 | 122.9 (1) | C4—C3—H3 | 116 (1) |
C2—C1—C6 | 118.8 (2) | C4—C5—H5 | 120 (1) |
C3—C2—C1 | 121.2 (2) | C6—C5—H5 | 119 (1) |
C2—C3—C4 | 120.7 (2) | O2—C7—H71 | 109 (2) |
O2—C4—C5 | 124.9 (2) | O2—C7—H72 | 104 (2) |
O2—C4—C3 | 116.1 (1) | H71—C7—H72 | 109 (2) |
C5—C4—C3 | 119.0 (2) | O2—C7—H73 | 111 (2) |
C4—C5—C6 | 121.1 (2) | H71—C7—H73 | 113 (2) |
C5—C6—C1 | 119.1 (1) | H72—C7—H73 | 112 (2) |
C5—C6—C8 | 118.8 (1) | N1—C8—H8 | 122 (1) |
C1—C6—C8 | 122.1 (1) | C6—C8—H8 | 118 (1) |
N1—C8—C6 | 120.3 (1) | C10—C11—H11 | 122 (1) |
O3—C9—N2 | 122.6 (1) | C12—C11—H11 | 119 (1) |
O3—C9—C10 | 122.0 (1) | C13—C12—H12 | 124 (1) |
N2—C9—C10 | 115.4 (1) | C11—C12—H12 | 116 (1) |
C11—C10—C15 | 120.5 (1) | C12—C13—H13 | 120 (1) |
C11—C10—C9 | 122.8 (1) | C14—C13—H13 | 120 (1) |
C15—C10—C9 | 116.6 (1) | C14—C15—H15 | 122 (1) |
C10—C11—C12 | 118.8 (2) | C10—C15—H15 | 118 (1) |
C13—C12—C11 | 120.5 (2) | O4—C16—H161 | 105 (2) |
C12—C13—C14 | 120.7 (2) | O4—C16—H162 | 108 (2) |
C13—C14—O4 | 115.8 (1) | H161—C16—H162 | 117 (2) |
C13—C14—C15 | 119.7 (2) | O4—C16—H163 | 108 (1) |
O4—C14—C15 | 124.5 (2) | H161—C16—H163 | 105 (2) |
C14—C15—C10 | 119.7 (1) | H162—C16—H163 | 114 (2) |
C1—O1—H1o | 104 (2) | ||
C8—N1—N2—C9 | 169.0 (1) | N1—N2—C9—O3 | −1.3 (2) |
O1—C1—C2—C3 | 177.8 (2) | N1—N2—C9—C10 | 177.1 (1) |
C6—C1—C2—C3 | −2.0 (2) | O3—C9—C10—C11 | −151.1 (2) |
C1—C2—C3—C4 | 1.4 (3) | N2—C9—C10—C11 | 30.5 (2) |
C7—O2—C4—C5 | 2.4 (3) | O3—C9—C10—C15 | 29.9 (2) |
C7—O2—C4—C3 | −177.1 (2) | N2—C9—C10—C15 | −148.5 (1) |
C2—C3—C4—O2 | 179.8 (2) | C15—C10—C11—C12 | 0.9 (2) |
C2—C3—C4—C5 | 0.2 (3) | C9—C10—C11—C12 | −178.1 (1) |
O2—C4—C5—C6 | 179.2 (1) | C10—C11—C12—C13 | 0.6 (3) |
C3—C4—C5—C6 | −1.3 (2) | C11—C12—C13—C14 | −0.6 (3) |
C4—C5—C6—C1 | 0.7 (2) | C12—C13—C14—O4 | 179.2 (2) |
C4—C5—C6—C8 | −178.9 (1) | C12—C13—C14—C15 | −0.8 (2) |
O1—C1—C6—C5 | −178.8 (1) | C16—O4—C14—C13 | −174.4 (2) |
C2—C1—C6—C5 | 1.0 (2) | C16—O4—C14—C15 | 5.5 (2) |
O1—C1—C6—C8 | 0.8 (2) | C13—C14—C15—C10 | 2.2 (2) |
C2—C1—C6—C8 | −179.5 (1) | O4—C14—C15—C10 | −177.7 (1) |
N2—N1—C8—C6 | 179.7 (1) | C11—C10—C15—C14 | −2.2 (2) |
C5—C6—C8—N1 | 172.0 (1) | C9—C10—C15—C14 | 176.7 (1) |
C1—C6—C8—N1 | −7.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.86 (1) | 1.84 (1) | 2.626 (2) | 151 (2) |
N2—H2n···O3i | 0.86 (1) | 2.04 (1) | 2.869 (2) | 164 (2) |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |