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organic compounds
The title compound, C16H16N2O4·H2O, crystallizes as a monohydrate in which the water molecule forms bifurcated hydrogen bonds to the hydroxyl and methoxy O atoms of the methoxysalicyldehyde portion of the Schiff base. The molecule is approximately planar; hydrogen-bonding interactions involving the amino group and the water molecule give rise to a layer structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019658/hg6085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019658/hg6085Isup2.hkl |
CCDC reference: 251723
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.102
- Data-to-parameter ratio = 9.2
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.830 0.979 Tmin' and Tmax expected: 0.960 0.979 RR' = 0.864 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Rat O1W -H1W1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Rat O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Rat O1W -H1# 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2073 Count of symmetry unique reflns 2082 Completeness (_total/calc) 99.57% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and POV-RAY (Cason, 2002); software used to prepare material for publication: SHELXL97.
3-Methoxysalicylaldehyde 4-methoxybenzoylhydrazone monohydrate top
Crystal data top
C16H16N2O4·H2O | F(000) = 672 |
Mr = 318.32 | Dx = 1.375 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 14318 reflections |
a = 5.013 (1) Å | θ = 3.0–27.5° |
b = 12.733 (3) Å | µ = 0.10 mm−1 |
c = 24.096 (5) Å | T = 295 K |
V = 1537.9 (5) Å3 | Prism, colorless |
Z = 4 | 0.39 × 0.26 × 0.21 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2073 independent reflections |
Radiation source: fine-focus sealed tube | 1784 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −6→5 |
Tmin = 0.830, Tmax = 0.979 | k = −16→16 |
14735 measured reflections | l = −31→31 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0563P)2 + 0.2354P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2073 reflections | Δρmax = 0.24 e Å−3 |
226 parameters | Δρmin = −0.12 e Å−3 |
5 restraints | Absolute structure: Calculation of Flack parameter suppressed |
Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.9600 (4) | 0.2929 (1) | 0.8360 (1) | 0.0491 (4) | |
O2 | 1.3161 (4) | 0.2777 (1) | 0.9132 (1) | 0.0526 (5) | |
O3 | 0.3954 (5) | 0.2700 (1) | 0.7073 (1) | 0.0632 (6) | |
O4 | −0.3348 (4) | 0.4834 (1) | 0.5240 (1) | 0.0577 (5) | |
O1w | 1.4487 (5) | 0.1620 (1) | 0.8032 (1) | 0.0614 (5) | |
N1 | 0.7224 (4) | 0.4108 (2) | 0.7571 (1) | 0.0425 (5) | |
N2 | 0.5456 (5) | 0.4367 (2) | 0.7153 (1) | 0.0432 (5) | |
C1 | 1.1032 (5) | 0.3805 (2) | 0.8460 (1) | 0.0383 (5) | |
C2 | 1.3005 (5) | 0.3740 (2) | 0.8876 (1) | 0.0405 (5) | |
C3 | 1.4591 (5) | 0.4595 (2) | 0.8995 (1) | 0.0457 (5) | |
C4 | 1.4263 (5) | 0.5527 (2) | 0.8707 (1) | 0.0483 (6) | |
C5 | 1.2340 (5) | 0.5607 (2) | 0.8301 (1) | 0.0475 (6) | |
C6 | 1.0702 (5) | 0.4748 (2) | 0.8170 (1) | 0.0397 (5) | |
C7 | 0.8729 (5) | 0.4866 (2) | 0.7730 (1) | 0.0451 (6) | |
C8 | 1.5353 (6) | 0.2607 (2) | 0.9498 (1) | 0.0569 (7) | |
C9 | 0.3854 (5) | 0.3624 (2) | 0.6929 (1) | 0.0430 (5) | |
C10 | 0.1971 (5) | 0.3978 (2) | 0.6488 (1) | 0.0389 (5) | |
C11 | 0.1569 (6) | 0.5022 (2) | 0.6331 (1) | 0.0467 (6) | |
C12 | −0.0233 (5) | 0.5274 (2) | 0.5920 (1) | 0.0489 (6) | |
C13 | −0.1676 (5) | 0.4499 (2) | 0.5652 (1) | 0.0429 (5) | |
C14 | −0.1360 (5) | 0.3458 (2) | 0.5813 (1) | 0.0464 (6) | |
C15 | 0.0441 (5) | 0.3216 (2) | 0.6225 (1) | 0.0462 (6) | |
C16 | −0.4836 (7) | 0.4068 (3) | 0.4947 (1) | 0.0722 (9) | |
H1o | 0.859 (5) | 0.304 (2) | 0.808 (1) | 0.06 (1)* | |
H1w1 | 1.334 (7) | 0.186 (3) | 0.826 (1) | 0.13 (2)* | |
H1w2 | 1.443 (7) | 0.202 (2) | 0.774 (1) | 0.08 (1)* | |
H2n | 0.528 (5) | 0.5001 (9) | 0.7052 (9) | 0.04 (1)* | |
H3 | 1.5887 | 0.4546 | 0.9270 | 0.055* | |
H4 | 1.5345 | 0.6100 | 0.8788 | 0.058* | |
H5 | 1.2124 | 0.6238 | 0.8111 | 0.057* | |
H7 | 0.8552 | 0.5517 | 0.7558 | 0.054* | |
H8a | 1.5216 | 0.3075 | 0.9809 | 0.085* | |
H8b | 1.6994 | 0.2736 | 0.9304 | 0.085* | |
H8c | 1.5324 | 0.1893 | 0.9627 | 0.085* | |
H11 | 0.2529 | 0.5553 | 0.6505 | 0.056* | |
H12 | −0.0483 | 0.5973 | 0.5822 | 0.059* | |
H14 | −0.2355 | 0.2930 | 0.5645 | 0.056* | |
H15 | 0.0640 | 0.2518 | 0.6331 | 0.055* | |
H16a | −0.6004 | 0.3708 | 0.5199 | 0.108* | |
H16b | −0.3638 | 0.3572 | 0.4779 | 0.108* | |
H16c | −0.5873 | 0.4404 | 0.4663 | 0.108* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.049 (1) | 0.045 (1) | 0.054 (1) | −0.005 (1) | −0.016 (1) | 0.001 (1) |
O2 | 0.055 (1) | 0.049 (1) | 0.054 (1) | −0.005 (1) | −0.018 (1) | 0.009 (1) |
O3 | 0.089 (2) | 0.038 (1) | 0.063 (1) | 0.007 (1) | −0.018 (1) | 0.009 (1) |
O4 | 0.059 (1) | 0.059 (1) | 0.055 (1) | 0.000 (1) | −0.018 (1) | 0.002 (1) |
O1w | 0.085 (2) | 0.044 (1) | 0.055 (1) | 0.009 (1) | −0.010 (1) | 0.000 (1) |
N1 | 0.045 (1) | 0.047 (1) | 0.035 (1) | 0.011 (1) | −0.002 (1) | 0.002 (1) |
N2 | 0.050 (1) | 0.040 (1) | 0.039 (1) | 0.007 (1) | −0.003 (1) | 0.005 (1) |
C1 | 0.037 (1) | 0.040 (1) | 0.038 (1) | 0.002 (1) | 0.002 (1) | −0.004 (1) |
C2 | 0.041 (1) | 0.042 (1) | 0.038 (1) | 0.003 (1) | 0.000 (1) | −0.002 (1) |
C3 | 0.041 (1) | 0.051 (1) | 0.045 (1) | 0.000 (1) | −0.002 (1) | −0.008 (1) |
C4 | 0.045 (1) | 0.041 (1) | 0.058 (1) | −0.006 (1) | 0.003 (1) | −0.009 (1) |
C5 | 0.050 (1) | 0.038 (1) | 0.055 (1) | 0.005 (1) | 0.011 (1) | 0.002 (1) |
C6 | 0.039 (1) | 0.042 (1) | 0.039 (1) | 0.008 (1) | 0.006 (1) | −0.001 (1) |
C7 | 0.048 (1) | 0.044 (1) | 0.044 (1) | 0.010 (1) | 0.004 (1) | 0.005 (1) |
C8 | 0.051 (2) | 0.069 (2) | 0.051 (1) | 0.002 (1) | −0.009 (1) | 0.012 (1) |
C9 | 0.051 (1) | 0.038 (1) | 0.039 (1) | 0.010 (1) | 0.003 (1) | 0.002 (1) |
C10 | 0.045 (1) | 0.035 (1) | 0.036 (1) | 0.005 (1) | 0.003 (1) | 0.002 (1) |
C11 | 0.058 (2) | 0.035 (1) | 0.047 (1) | −0.001 (1) | −0.010 (1) | −0.002 (1) |
C12 | 0.059 (2) | 0.035 (1) | 0.053 (1) | 0.003 (1) | −0.010 (1) | 0.004 (1) |
C13 | 0.041 (1) | 0.048 (1) | 0.040 (1) | 0.002 (1) | −0.001 (1) | 0.000 (1) |
C14 | 0.046 (1) | 0.042 (1) | 0.052 (1) | −0.005 (1) | −0.002 (1) | −0.006 (1) |
C15 | 0.056 (1) | 0.032 (1) | 0.051 (1) | 0.000 (1) | 0.003 (1) | 0.001 (1) |
C16 | 0.064 (2) | 0.087 (2) | 0.066 (2) | −0.010 (2) | −0.023 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.348 (3) | C13—C14 | 1.391 (3) |
O2—C2 | 1.373 (3) | C14—C15 | 1.376 (3) |
O2—C8 | 1.426 (3) | O1—H1o | 0.85 (1) |
O3—C9 | 1.228 (3) | O1w—H1w1 | 0.86 (1) |
O4—C13 | 1.367 (3) | O1w—H1w2 | 0.87 (1) |
O4—C16 | 1.417 (3) | N2—H2n | 0.85 (1) |
N1—N2 | 1.382 (3) | C3—H3 | 0.93 |
N1—C7 | 1.284 (3) | C4—H4 | 0.93 |
N2—C9 | 1.353 (3) | C5—H5 | 0.93 |
C1—C2 | 1.411 (3) | C7—H7 | 0.93 |
C1—C6 | 1.399 (3) | C8—H8a | 0.96 |
C2—C3 | 1.379 (3) | C8—H8b | 0.96 |
C3—C4 | 1.384 (3) | C8—H8c | 0.96 |
C4—C5 | 1.377 (4) | C11—H11 | 0.93 |
C5—C6 | 1.404 (3) | C12—H12 | 0.93 |
C6—C7 | 1.458 (3) | C14—H14 | 0.93 |
C9—C10 | 1.490 (3) | C15—H15 | 0.93 |
C10—C15 | 1.390 (3) | C16—H16a | 0.96 |
C10—C11 | 1.398 (3) | C16—H16b | 0.96 |
C11—C12 | 1.377 (3) | C16—H16c | 0.96 |
C12—C13 | 1.383 (3) | ||
C2—O2—C8 | 117.2 (2) | H1w1—O1w—H1w2 | 107 (2) |
C13—O4—C16 | 118.1 (2) | C9—N2—H2n | 119 (2) |
C7—N1—N2 | 114.5 (2) | N1—N2—H2n | 120 (2) |
C9—N2—N1 | 120.3 (2) | C2—C3—H3 | 119.8 |
O1—C1—C2 | 116.8 (2) | C4—C3—H3 | 119.8 |
O1—C1—C6 | 123.9 (2) | C5—C4—H4 | 119.9 |
O2—C2—C1 | 114.3 (2) | C3—C4—H4 | 119.9 |
O2—C2—C3 | 125.4 (2) | C4—C5—H5 | 119.6 |
C6—C1—C2 | 119.3 (2) | C6—C5—H5 | 119.6 |
C3—C2—C1 | 120.3 (2) | N1—C7—H7 | 118.7 |
C2—C3—C4 | 120.3 (2) | C6—C7—H7 | 118.7 |
C5—C4—C3 | 120.2 (2) | O2—C8—H8a | 109.5 |
C4—C5—C6 | 120.7 (2) | O2—C8—H8b | 109.5 |
C1—C6—C5 | 119.2 (2) | H8a—C8—H8b | 109.5 |
C1—C6—C7 | 122.2 (2) | O2—C8—H8c | 109.5 |
C5—C6—C7 | 118.6 (2) | H8a—C8—H8c | 109.5 |
N1—C7—C6 | 122.6 (2) | H8b—C8—H8c | 109.5 |
O3—C9—N2 | 122.1 (2) | C12—C11—H11 | 119.6 |
O3—C9—C10 | 121.2 (2) | C10—C11—H11 | 119.6 |
N2—C9—C10 | 116.7 (2) | C11—C12—H12 | 119.6 |
C15—C10—C11 | 117.5 (2) | C13—C12—H12 | 119.6 |
C15—C10—C9 | 117.6 (2) | C15—C14—H14 | 120.3 |
C11—C10—C9 | 124.9 (2) | C13—C14—H14 | 120.3 |
C12—C11—C10 | 120.7 (2) | C14—C15—H15 | 118.9 |
C11—C12—C13 | 120.9 (2) | C10—C15—H15 | 118.9 |
O4—C13—C12 | 116.0 (2) | O4—C16—H16a | 109.5 |
O4—C13—C14 | 124.7 (2) | O4—C16—H16b | 109.5 |
C12—C13—C14 | 119.3 (2) | H16a—C16—H16b | 109.5 |
C15—C14—C13 | 119.3 (2) | O4—C16—H16c | 109.5 |
C14—C15—C10 | 122.3 (2) | H16a—C16—H16c | 109.5 |
C1—O1—H1o | 109 (2) | H16b—C16—H16c | 109.5 |
C7—N1—N2—C9 | 176.7 (2) | C5—C6—C7—N1 | 177.3 (2) |
C8—O2—C2—C3 | −8.4 (3) | N1—N2—C9—O3 | −2.1 (4) |
C8—O2—C2—C1 | 171.1 (2) | N1—N2—C9—C10 | 178.8 (2) |
O1—C1—C2—O2 | −1.0 (3) | O3—C9—C10—C15 | −3.5 (3) |
C6—C1—C2—O2 | −179.7 (2) | N2—C9—C10—C15 | 175.6 (2) |
O1—C1—C2—C3 | 178.6 (2) | O3—C9—C10—C11 | 174.4 (3) |
C6—C1—C2—C3 | −0.1 (3) | N2—C9—C10—C11 | −6.5 (3) |
O2—C2—C3—C4 | 179.5 (2) | C15—C10—C11—C12 | −1.6 (4) |
C1—C2—C3—C4 | 0.0 (4) | C9—C10—C11—C12 | −179.5 (2) |
C2—C3—C4—C5 | 0.3 (4) | C10—C11—C12—C13 | −0.4 (4) |
C3—C4—C5—C6 | −0.5 (4) | C16—O4—C13—C12 | 178.9 (2) |
O1—C1—C6—C5 | −178.7 (2) | C16—O4—C13—C14 | −1.3 (4) |
C2—C1—C6—C5 | −0.1 (3) | C11—C12—C13—O4 | −178.1 (2) |
O1—C1—C6—C7 | 0.5 (3) | C11—C12—C13—C14 | 2.2 (4) |
C2—C1—C6—C7 | 179.1 (2) | O4—C13—C14—C15 | 178.3 (2) |
C4—C5—C6—C1 | 0.4 (3) | C12—C13—C14—C15 | −1.9 (4) |
C4—C5—C6—C7 | −178.9 (2) | C13—C14—C15—C10 | −0.1 (4) |
N2—N1—C7—C6 | 179.4 (2) | C11—C10—C15—C14 | 1.8 (4) |
C1—C6—C7—N1 | −2.0 (3) | C9—C10—C15—C14 | 179.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.85 (1) | 1.96 (2) | 2.700 (2) | 145 (3) |
O1w—H1w1···O1 | 0.86 (1) | 2.33 (2) | 3.067 (3) | 145 (3) |
O1w—H1w1···O2 | 0.86 (1) | 2.40 (3) | 3.104 (3) | 140 (4) |
O1w—H1w2···O3i | 0.87 (1) | 1.84 (1) | 2.701 (2) | 171 (3) |
N2—H2n···O1wii | 0.85 (1) | 2.08 (1) | 2.904 (3) | 165 (2) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+3/2. |
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