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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019658/hg6085sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019658/hg6085Isup2.hkl
Contains datablock I

CCDC reference: 251723

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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·H2OF(000) = 672
Mr = 318.32Dx = 1.375 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 14318 reflections
a = 5.013 (1) Åθ = 3.0–27.5°
b = 12.733 (3) ŵ = 0.10 mm1
c = 24.096 (5) ÅT = 295 K
V = 1537.9 (5) Å3Prism, colorless
Z = 40.39 × 0.26 × 0.21 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2073 independent reflections
Radiation source: fine-focus sealed tube1784 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 65
Tmin = 0.830, Tmax = 0.979k = 1616
14735 measured reflectionsl = 3131
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)] = 0.041H 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 reflectionsΔρmax = 0.24 e Å3
226 parametersΔρmin = 0.12 e Å3
5 restraintsAbsolute 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
xyzUiso*/Ueq
O10.9600 (4)0.2929 (1)0.8360 (1)0.0491 (4)
O21.3161 (4)0.2777 (1)0.9132 (1)0.0526 (5)
O30.3954 (5)0.2700 (1)0.7073 (1)0.0632 (6)
O40.3348 (4)0.4834 (1)0.5240 (1)0.0577 (5)
O1w1.4487 (5)0.1620 (1)0.8032 (1)0.0614 (5)
N10.7224 (4)0.4108 (2)0.7571 (1)0.0425 (5)
N20.5456 (5)0.4367 (2)0.7153 (1)0.0432 (5)
C11.1032 (5)0.3805 (2)0.8460 (1)0.0383 (5)
C21.3005 (5)0.3740 (2)0.8876 (1)0.0405 (5)
C31.4591 (5)0.4595 (2)0.8995 (1)0.0457 (5)
C41.4263 (5)0.5527 (2)0.8707 (1)0.0483 (6)
C51.2340 (5)0.5607 (2)0.8301 (1)0.0475 (6)
C61.0702 (5)0.4748 (2)0.8170 (1)0.0397 (5)
C70.8729 (5)0.4866 (2)0.7730 (1)0.0451 (6)
C81.5353 (6)0.2607 (2)0.9498 (1)0.0569 (7)
C90.3854 (5)0.3624 (2)0.6929 (1)0.0430 (5)
C100.1971 (5)0.3978 (2)0.6488 (1)0.0389 (5)
C110.1569 (6)0.5022 (2)0.6331 (1)0.0467 (6)
C120.0233 (5)0.5274 (2)0.5920 (1)0.0489 (6)
C130.1676 (5)0.4499 (2)0.5652 (1)0.0429 (5)
C140.1360 (5)0.3458 (2)0.5813 (1)0.0464 (6)
C150.0441 (5)0.3216 (2)0.6225 (1)0.0462 (6)
C160.4836 (7)0.4068 (3)0.4947 (1)0.0722 (9)
H1o0.859 (5)0.304 (2)0.808 (1)0.06 (1)*
H1w11.334 (7)0.186 (3)0.826 (1)0.13 (2)*
H1w21.443 (7)0.202 (2)0.774 (1)0.08 (1)*
H2n0.528 (5)0.5001 (9)0.7052 (9)0.04 (1)*
H31.58870.45460.92700.055*
H41.53450.61000.87880.058*
H51.21240.62380.81110.057*
H70.85520.55170.75580.054*
H8a1.52160.30750.98090.085*
H8b1.69940.27360.93040.085*
H8c1.53240.18930.96270.085*
H110.25290.55530.65050.056*
H120.04830.59730.58220.059*
H140.23550.29300.56450.056*
H150.06400.25180.63310.055*
H16a0.60040.37080.51990.108*
H16b0.36380.35720.47790.108*
H16c0.58730.44040.46630.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.049 (1)0.045 (1)0.054 (1)0.005 (1)0.016 (1)0.001 (1)
O20.055 (1)0.049 (1)0.054 (1)0.005 (1)0.018 (1)0.009 (1)
O30.089 (2)0.038 (1)0.063 (1)0.007 (1)0.018 (1)0.009 (1)
O40.059 (1)0.059 (1)0.055 (1)0.000 (1)0.018 (1)0.002 (1)
O1w0.085 (2)0.044 (1)0.055 (1)0.009 (1)0.010 (1)0.000 (1)
N10.045 (1)0.047 (1)0.035 (1)0.011 (1)0.002 (1)0.002 (1)
N20.050 (1)0.040 (1)0.039 (1)0.007 (1)0.003 (1)0.005 (1)
C10.037 (1)0.040 (1)0.038 (1)0.002 (1)0.002 (1)0.004 (1)
C20.041 (1)0.042 (1)0.038 (1)0.003 (1)0.000 (1)0.002 (1)
C30.041 (1)0.051 (1)0.045 (1)0.000 (1)0.002 (1)0.008 (1)
C40.045 (1)0.041 (1)0.058 (1)0.006 (1)0.003 (1)0.009 (1)
C50.050 (1)0.038 (1)0.055 (1)0.005 (1)0.011 (1)0.002 (1)
C60.039 (1)0.042 (1)0.039 (1)0.008 (1)0.006 (1)0.001 (1)
C70.048 (1)0.044 (1)0.044 (1)0.010 (1)0.004 (1)0.005 (1)
C80.051 (2)0.069 (2)0.051 (1)0.002 (1)0.009 (1)0.012 (1)
C90.051 (1)0.038 (1)0.039 (1)0.010 (1)0.003 (1)0.002 (1)
C100.045 (1)0.035 (1)0.036 (1)0.005 (1)0.003 (1)0.002 (1)
C110.058 (2)0.035 (1)0.047 (1)0.001 (1)0.010 (1)0.002 (1)
C120.059 (2)0.035 (1)0.053 (1)0.003 (1)0.010 (1)0.004 (1)
C130.041 (1)0.048 (1)0.040 (1)0.002 (1)0.001 (1)0.000 (1)
C140.046 (1)0.042 (1)0.052 (1)0.005 (1)0.002 (1)0.006 (1)
C150.056 (1)0.032 (1)0.051 (1)0.000 (1)0.003 (1)0.001 (1)
C160.064 (2)0.087 (2)0.066 (2)0.010 (2)0.023 (2)0.000 (2)
Geometric parameters (Å, º) top
O1—C11.348 (3)C13—C141.391 (3)
O2—C21.373 (3)C14—C151.376 (3)
O2—C81.426 (3)O1—H1o0.85 (1)
O3—C91.228 (3)O1w—H1w10.86 (1)
O4—C131.367 (3)O1w—H1w20.87 (1)
O4—C161.417 (3)N2—H2n0.85 (1)
N1—N21.382 (3)C3—H30.93
N1—C71.284 (3)C4—H40.93
N2—C91.353 (3)C5—H50.93
C1—C21.411 (3)C7—H70.93
C1—C61.399 (3)C8—H8a0.96
C2—C31.379 (3)C8—H8b0.96
C3—C41.384 (3)C8—H8c0.96
C4—C51.377 (4)C11—H110.93
C5—C61.404 (3)C12—H120.93
C6—C71.458 (3)C14—H140.93
C9—C101.490 (3)C15—H150.93
C10—C151.390 (3)C16—H16a0.96
C10—C111.398 (3)C16—H16b0.96
C11—C121.377 (3)C16—H16c0.96
C12—C131.383 (3)
C2—O2—C8117.2 (2)H1w1—O1w—H1w2107 (2)
C13—O4—C16118.1 (2)C9—N2—H2n119 (2)
C7—N1—N2114.5 (2)N1—N2—H2n120 (2)
C9—N2—N1120.3 (2)C2—C3—H3119.8
O1—C1—C2116.8 (2)C4—C3—H3119.8
O1—C1—C6123.9 (2)C5—C4—H4119.9
O2—C2—C1114.3 (2)C3—C4—H4119.9
O2—C2—C3125.4 (2)C4—C5—H5119.6
C6—C1—C2119.3 (2)C6—C5—H5119.6
C3—C2—C1120.3 (2)N1—C7—H7118.7
C2—C3—C4120.3 (2)C6—C7—H7118.7
C5—C4—C3120.2 (2)O2—C8—H8a109.5
C4—C5—C6120.7 (2)O2—C8—H8b109.5
C1—C6—C5119.2 (2)H8a—C8—H8b109.5
C1—C6—C7122.2 (2)O2—C8—H8c109.5
C5—C6—C7118.6 (2)H8a—C8—H8c109.5
N1—C7—C6122.6 (2)H8b—C8—H8c109.5
O3—C9—N2122.1 (2)C12—C11—H11119.6
O3—C9—C10121.2 (2)C10—C11—H11119.6
N2—C9—C10116.7 (2)C11—C12—H12119.6
C15—C10—C11117.5 (2)C13—C12—H12119.6
C15—C10—C9117.6 (2)C15—C14—H14120.3
C11—C10—C9124.9 (2)C13—C14—H14120.3
C12—C11—C10120.7 (2)C14—C15—H15118.9
C11—C12—C13120.9 (2)C10—C15—H15118.9
O4—C13—C12116.0 (2)O4—C16—H16a109.5
O4—C13—C14124.7 (2)O4—C16—H16b109.5
C12—C13—C14119.3 (2)H16a—C16—H16b109.5
C15—C14—C13119.3 (2)O4—C16—H16c109.5
C14—C15—C10122.3 (2)H16a—C16—H16c109.5
C1—O1—H1o109 (2)H16b—C16—H16c109.5
C7—N1—N2—C9176.7 (2)C5—C6—C7—N1177.3 (2)
C8—O2—C2—C38.4 (3)N1—N2—C9—O32.1 (4)
C8—O2—C2—C1171.1 (2)N1—N2—C9—C10178.8 (2)
O1—C1—C2—O21.0 (3)O3—C9—C10—C153.5 (3)
C6—C1—C2—O2179.7 (2)N2—C9—C10—C15175.6 (2)
O1—C1—C2—C3178.6 (2)O3—C9—C10—C11174.4 (3)
C6—C1—C2—C30.1 (3)N2—C9—C10—C116.5 (3)
O2—C2—C3—C4179.5 (2)C15—C10—C11—C121.6 (4)
C1—C2—C3—C40.0 (4)C9—C10—C11—C12179.5 (2)
C2—C3—C4—C50.3 (4)C10—C11—C12—C130.4 (4)
C3—C4—C5—C60.5 (4)C16—O4—C13—C12178.9 (2)
O1—C1—C6—C5178.7 (2)C16—O4—C13—C141.3 (4)
C2—C1—C6—C50.1 (3)C11—C12—C13—O4178.1 (2)
O1—C1—C6—C70.5 (3)C11—C12—C13—C142.2 (4)
C2—C1—C6—C7179.1 (2)O4—C13—C14—C15178.3 (2)
C4—C5—C6—C10.4 (3)C12—C13—C14—C151.9 (4)
C4—C5—C6—C7178.9 (2)C13—C14—C15—C100.1 (4)
N2—N1—C7—C6179.4 (2)C11—C10—C15—C141.8 (4)
C1—C6—C7—N12.0 (3)C9—C10—C15—C14179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.85 (1)1.96 (2)2.700 (2)145 (3)
O1w—H1w1···O10.86 (1)2.33 (2)3.067 (3)145 (3)
O1w—H1w1···O20.86 (1)2.40 (3)3.104 (3)140 (4)
O1w—H1w2···O3i0.87 (1)1.84 (1)2.701 (2)171 (3)
N2—H2n···O1wii0.85 (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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