Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030655/ac6197sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030655/ac6197Isup2.hkl |
CCDC reference: 287430
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.129
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
To a solution of 4-hydroxy-3-methoxybenzaldehyde (15.2 g, 10 mmol) and potassium carbonate (13.8 g, 10 mmol) in acetonitrile (500 ml), 2-chloroethanol (8.5 g, 10 mmol) was added in 30 min, and the mixture was refluxed for 24 h under nitrogen. The solvent was removed and the resultant oil was poured into ice water (500 ml). Then the white precipitate was isolated and recrystallized from ethanol to give 4-(2-hydroxyethoxy)-3-methoxybenzaldehyde in 43% yield. An anhydrous ethanol solution of 4-(2-hydroxyethoxy)-3-methoxybenzaldehyde (1.96 g, 10 mmol) was added to an anhydrous ethanol solution of benzohydrazide (1.36 g, 10 mmol) and the mixture was stirred at 350 K for 5 h under nitrogen, whereupon a yellow precipitate appeared. The product was isolated and recrystallized from ethanol, and then dried in vacuo to give the pure compound in 83% yield. Colorless single crystals of (1) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.
H atoms bonded to C atoms were included in calculated positions (C—H = 0.93–0.96 Å) and refined using a riding-model approximation, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The H atoms attached to O and N atoms were located in a difference Fourier map and refined freely.
Data collection: SMART (Bruker, 1999); 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.
Fig. 1. A view of the title compound with 30% probability displacement ellipsoids. | |
Fig. 2. Intermolecular hydrogen-bonding interactions (dashed lines). |
C17H18N2O4·H2O | F(000) = 704 |
Mr = 332.35 | Dx = 1.290 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.924 (2) Å | Cell parameters from 2599 reflections |
b = 11.936 (3) Å | θ = 2.2–25.8° |
c = 14.890 (4) Å | µ = 0.10 mm−1 |
β = 104.003 (4)° | T = 294 K |
V = 1711.5 (7) Å3 | Block, colorless |
Z = 4 | 0.46 × 0.40 × 0.30 mm |
Bruker SMART CCD area-detector diffractometer | 3508 independent reflections |
Radiation source: fine-focus sealed tube | 2112 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ and ω scans | θmax = 26.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −9→12 |
Tmin = 0.948, Tmax = 0.972 | k = −14→14 |
9477 measured reflections | l = −18→9 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.3524P] where P = (Fo2 + 2Fc2)/3 |
3508 reflections | (Δ/σ)max = 0.001 |
234 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C17H18N2O4·H2O | V = 1711.5 (7) Å3 |
Mr = 332.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.924 (2) Å | µ = 0.10 mm−1 |
b = 11.936 (3) Å | T = 294 K |
c = 14.890 (4) Å | 0.46 × 0.40 × 0.30 mm |
β = 104.003 (4)° |
Bruker SMART CCD area-detector diffractometer | 3508 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2112 reflections with I > 2σ(I) |
Tmin = 0.948, Tmax = 0.972 | Rint = 0.031 |
9477 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.23 e Å−3 |
3508 reflections | Δρmin = −0.20 e Å−3 |
234 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.66545 (16) | 0.59338 (13) | 0.01994 (11) | 0.0628 (4) | |
H1 | 0.694 (3) | 0.563 (2) | −0.026 (2) | 0.097 (9)* | |
O2 | 0.56987 (13) | 0.77031 (11) | 0.11182 (9) | 0.0495 (4) | |
O3 | 0.74584 (15) | 0.90771 (12) | 0.20585 (9) | 0.0592 (4) | |
O4 | 0.81197 (15) | 1.04064 (13) | 0.65683 (9) | 0.0591 (4) | |
N1 | 0.64359 (16) | 0.91330 (13) | 0.53297 (10) | 0.0424 (4) | |
N2 | 0.63220 (18) | 0.92098 (14) | 0.62356 (11) | 0.0434 (4) | |
H2 | 0.569 (2) | 0.8849 (19) | 0.6396 (15) | 0.065 (7)* | |
C1 | 0.55696 (19) | 0.83265 (15) | 0.38326 (12) | 0.0405 (4) | |
C2 | 0.65512 (19) | 0.88345 (16) | 0.34299 (12) | 0.0422 (5) | |
H2A | 0.7207 | 0.9320 | 0.3778 | 0.051* | |
C3 | 0.65524 (18) | 0.86195 (15) | 0.25231 (12) | 0.0403 (4) | |
C4 | 0.55733 (19) | 0.78856 (15) | 0.19950 (13) | 0.0399 (4) | |
C5 | 0.4581 (2) | 0.74125 (16) | 0.23835 (14) | 0.0469 (5) | |
H5 | 0.3905 | 0.6946 | 0.2031 | 0.056* | |
C6 | 0.4587 (2) | 0.76303 (16) | 0.32977 (14) | 0.0474 (5) | |
H6 | 0.3918 | 0.7302 | 0.3555 | 0.057* | |
C7 | 0.4792 (2) | 0.69089 (18) | 0.05561 (14) | 0.0526 (5) | |
H7A | 0.3894 | 0.7248 | 0.0296 | 0.063* | |
H7B | 0.4659 | 0.6268 | 0.0925 | 0.063* | |
C8 | 0.5441 (2) | 0.65502 (19) | −0.01967 (14) | 0.0578 (6) | |
H8A | 0.4798 | 0.6089 | −0.0639 | 0.069* | |
H8B | 0.5675 | 0.7201 | −0.0519 | 0.069* | |
C9 | 0.8229 (2) | 1.0031 (2) | 0.24390 (15) | 0.0633 (6) | |
H9A | 0.7617 | 1.0574 | 0.2606 | 0.095* | |
H9B | 0.8667 | 1.0351 | 0.1990 | 0.095* | |
H9C | 0.8925 | 0.9819 | 0.2980 | 0.095* | |
C10 | 0.5550 (2) | 0.85139 (16) | 0.47980 (13) | 0.0442 (5) | |
H10 | 0.4865 | 0.8169 | 0.5031 | 0.053* | |
C11 | 0.7221 (2) | 0.98739 (16) | 0.68209 (13) | 0.0430 (5) | |
C12 | 0.7125 (2) | 0.99192 (16) | 0.78097 (13) | 0.0457 (5) | |
C13 | 0.6075 (2) | 0.94249 (19) | 0.81319 (14) | 0.0593 (6) | |
H13 | 0.5373 | 0.9035 | 0.7726 | 0.071* | |
C14 | 0.6065 (3) | 0.9507 (2) | 0.90572 (18) | 0.0796 (8) | |
H14 | 0.5347 | 0.9184 | 0.9269 | 0.095* | |
C15 | 0.7103 (4) | 1.0061 (3) | 0.96569 (18) | 0.0915 (9) | |
H15 | 0.7110 | 1.0093 | 1.0282 | 0.110* | |
C16 | 0.8134 (3) | 1.0568 (3) | 0.93457 (18) | 0.0932 (9) | |
H16 | 0.8830 | 1.0960 | 0.9756 | 0.112* | |
C17 | 0.8146 (3) | 1.0502 (2) | 0.84223 (16) | 0.0688 (7) | |
H17 | 0.8849 | 1.0853 | 0.8213 | 0.083* | |
O5 | 0.3840 (2) | 0.7919 (2) | 0.63922 (16) | 0.0785 (6) | |
H5A | 0.357 (3) | 0.740 (3) | 0.656 (2) | 0.111 (14)* | |
H5B | 0.311 (4) | 0.826 (3) | 0.599 (3) | 0.147 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0692 (10) | 0.0680 (10) | 0.0532 (9) | 0.0180 (8) | 0.0191 (8) | −0.0128 (8) |
O2 | 0.0537 (8) | 0.0503 (8) | 0.0483 (8) | −0.0103 (6) | 0.0197 (6) | −0.0197 (6) |
O3 | 0.0647 (9) | 0.0678 (10) | 0.0545 (9) | −0.0291 (8) | 0.0325 (7) | −0.0217 (7) |
O4 | 0.0611 (9) | 0.0690 (10) | 0.0527 (9) | −0.0149 (8) | 0.0247 (7) | −0.0030 (7) |
N1 | 0.0453 (9) | 0.0484 (9) | 0.0372 (9) | 0.0043 (8) | 0.0172 (7) | 0.0022 (7) |
N2 | 0.0474 (10) | 0.0491 (10) | 0.0376 (9) | 0.0003 (8) | 0.0181 (8) | 0.0028 (8) |
C1 | 0.0401 (10) | 0.0400 (10) | 0.0437 (11) | 0.0056 (8) | 0.0147 (8) | 0.0003 (8) |
C2 | 0.0386 (10) | 0.0458 (11) | 0.0429 (11) | −0.0039 (9) | 0.0111 (8) | −0.0071 (9) |
C3 | 0.0392 (10) | 0.0407 (10) | 0.0440 (11) | −0.0033 (8) | 0.0161 (9) | −0.0050 (8) |
C4 | 0.0420 (10) | 0.0356 (10) | 0.0447 (11) | 0.0018 (8) | 0.0155 (9) | −0.0080 (8) |
C5 | 0.0424 (11) | 0.0428 (11) | 0.0571 (13) | −0.0074 (9) | 0.0153 (9) | −0.0132 (9) |
C6 | 0.0439 (11) | 0.0462 (11) | 0.0573 (13) | −0.0060 (9) | 0.0223 (10) | −0.0036 (10) |
C7 | 0.0480 (11) | 0.0529 (12) | 0.0536 (12) | −0.0003 (10) | 0.0060 (10) | −0.0184 (10) |
C8 | 0.0694 (14) | 0.0565 (13) | 0.0446 (12) | 0.0035 (11) | 0.0083 (11) | −0.0116 (10) |
C9 | 0.0680 (14) | 0.0742 (15) | 0.0507 (13) | −0.0315 (13) | 0.0200 (11) | −0.0088 (12) |
C10 | 0.0455 (11) | 0.0455 (11) | 0.0460 (11) | 0.0014 (9) | 0.0198 (9) | 0.0025 (9) |
C11 | 0.0459 (11) | 0.0425 (11) | 0.0437 (11) | 0.0091 (9) | 0.0168 (9) | 0.0054 (9) |
C12 | 0.0545 (12) | 0.0450 (11) | 0.0390 (11) | 0.0126 (10) | 0.0142 (10) | 0.0043 (9) |
C13 | 0.0784 (15) | 0.0595 (14) | 0.0465 (12) | 0.0009 (12) | 0.0279 (12) | 0.0049 (10) |
C14 | 0.117 (2) | 0.0751 (17) | 0.0589 (16) | 0.0097 (17) | 0.0459 (17) | 0.0123 (14) |
C15 | 0.134 (3) | 0.102 (2) | 0.0406 (14) | 0.022 (2) | 0.0246 (17) | 0.0000 (15) |
C16 | 0.103 (2) | 0.116 (2) | 0.0552 (17) | 0.000 (2) | 0.0086 (16) | −0.0238 (16) |
C17 | 0.0726 (16) | 0.0794 (17) | 0.0543 (14) | 0.0022 (13) | 0.0153 (12) | −0.0113 (12) |
O5 | 0.0589 (11) | 0.0880 (14) | 0.0918 (14) | −0.0126 (11) | 0.0243 (10) | 0.0227 (12) |
O1—C8 | 1.412 (2) | C7—H7A | 0.9700 |
O1—H1 | 0.88 (3) | C7—H7B | 0.9700 |
O2—C4 | 1.359 (2) | C8—H8A | 0.9700 |
O2—C7 | 1.430 (2) | C8—H8B | 0.9700 |
O3—C3 | 1.374 (2) | C9—H9A | 0.9600 |
O3—C9 | 1.412 (2) | C9—H9B | 0.9600 |
O4—C11 | 1.226 (2) | C9—H9C | 0.9600 |
N1—C10 | 1.269 (2) | C10—H10 | 0.9300 |
N1—N2 | 1.384 (2) | C11—C12 | 1.499 (3) |
N2—C11 | 1.345 (3) | C12—C17 | 1.377 (3) |
N2—H2 | 0.84 (2) | C12—C13 | 1.380 (3) |
C1—C6 | 1.378 (3) | C13—C14 | 1.384 (3) |
C1—C2 | 1.400 (3) | C13—H13 | 0.9300 |
C1—C10 | 1.460 (3) | C14—C15 | 1.360 (4) |
C2—C3 | 1.375 (2) | C14—H14 | 0.9300 |
C2—H2A | 0.9300 | C15—C16 | 1.363 (4) |
C3—C4 | 1.400 (3) | C15—H15 | 0.9300 |
C4—C5 | 1.378 (3) | C16—C17 | 1.380 (3) |
C5—C6 | 1.384 (3) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—H6 | 0.9300 | O5—H5A | 0.74 (4) |
C7—C8 | 1.485 (3) | O5—H5B | 0.92 (4) |
C8—O1—H1 | 107.2 (18) | O1—C8—H8B | 110.0 |
C4—O2—C7 | 118.55 (15) | C7—C8—H8B | 110.0 |
C3—O3—C9 | 118.40 (15) | H8A—C8—H8B | 108.4 |
C10—N1—N2 | 116.04 (16) | O3—C9—H9A | 109.5 |
C11—N2—N1 | 118.22 (17) | O3—C9—H9B | 109.5 |
C11—N2—H2 | 122.8 (15) | H9A—C9—H9B | 109.5 |
N1—N2—H2 | 119.0 (15) | O3—C9—H9C | 109.5 |
C6—C1—C2 | 118.81 (17) | H9A—C9—H9C | 109.5 |
C6—C1—C10 | 119.02 (17) | H9B—C9—H9C | 109.5 |
C2—C1—C10 | 122.16 (17) | N1—C10—C1 | 122.08 (17) |
C3—C2—C1 | 120.40 (17) | N1—C10—H10 | 119.0 |
C3—C2—H2A | 119.8 | C1—C10—H10 | 119.0 |
C1—C2—H2A | 119.8 | O4—C11—N2 | 121.66 (17) |
O3—C3—C2 | 125.22 (17) | O4—C11—C12 | 120.44 (19) |
O3—C3—C4 | 114.58 (15) | N2—C11—C12 | 117.87 (17) |
C2—C3—C4 | 120.20 (17) | C17—C12—C13 | 118.84 (19) |
O2—C4—C5 | 125.35 (17) | C17—C12—C11 | 117.19 (19) |
O2—C4—C3 | 115.31 (16) | C13—C12—C11 | 123.97 (19) |
C5—C4—C3 | 119.34 (17) | C12—C13—C14 | 120.3 (2) |
C4—C5—C6 | 120.14 (18) | C12—C13—H13 | 119.9 |
C4—C5—H5 | 119.9 | C14—C13—H13 | 119.9 |
C6—C5—H5 | 119.9 | C15—C14—C13 | 120.1 (3) |
C1—C6—C5 | 121.05 (18) | C15—C14—H14 | 120.0 |
C1—C6—H6 | 119.5 | C13—C14—H14 | 120.0 |
C5—C6—H6 | 119.5 | C14—C15—C16 | 120.3 (2) |
O2—C7—C8 | 107.86 (16) | C14—C15—H15 | 119.9 |
O2—C7—H7A | 110.1 | C16—C15—H15 | 119.9 |
C8—C7—H7A | 110.1 | C15—C16—C17 | 120.1 (3) |
O2—C7—H7B | 110.1 | C15—C16—H16 | 119.9 |
C8—C7—H7B | 110.1 | C17—C16—H16 | 119.9 |
H7A—C7—H7B | 108.4 | C12—C17—C16 | 120.4 (3) |
O1—C8—C7 | 108.46 (17) | C12—C17—H17 | 119.8 |
O1—C8—H8A | 110.0 | C16—C17—H17 | 119.8 |
C7—C8—H8A | 110.0 | H5A—O5—H5B | 107 (3) |
C10—N1—N2—C11 | −178.71 (17) | O2—C7—C8—O1 | 67.3 (2) |
C6—C1—C2—C3 | −1.5 (3) | N2—N1—C10—C1 | −178.07 (16) |
C10—C1—C2—C3 | 178.72 (17) | C6—C1—C10—N1 | 179.04 (18) |
C9—O3—C3—C2 | −16.2 (3) | C2—C1—C10—N1 | −1.2 (3) |
C9—O3—C3—C4 | 163.54 (18) | N1—N2—C11—O4 | 0.3 (3) |
C1—C2—C3—O3 | 179.49 (18) | N1—N2—C11—C12 | −177.76 (15) |
C1—C2—C3—C4 | −0.3 (3) | O4—C11—C12—C17 | −5.2 (3) |
C7—O2—C4—C5 | −3.9 (3) | N2—C11—C12—C17 | 172.95 (19) |
C7—O2—C4—C3 | 176.08 (16) | O4—C11—C12—C13 | 174.15 (19) |
O3—C3—C4—O2 | 2.4 (2) | N2—C11—C12—C13 | −7.7 (3) |
C2—C3—C4—O2 | −177.79 (16) | C17—C12—C13—C14 | −0.7 (3) |
O3—C3—C4—C5 | −177.55 (17) | C11—C12—C13—C14 | −180.0 (2) |
C2—C3—C4—C5 | 2.2 (3) | C12—C13—C14—C15 | −1.1 (4) |
O2—C4—C5—C6 | 177.64 (18) | C13—C14—C15—C16 | 2.2 (4) |
C3—C4—C5—C6 | −2.4 (3) | C14—C15—C16—C17 | −1.5 (5) |
C2—C1—C6—C5 | 1.4 (3) | C13—C12—C17—C16 | 1.4 (3) |
C10—C1—C6—C5 | −178.86 (18) | C11—C12—C17—C16 | −179.2 (2) |
C4—C5—C6—C1 | 0.6 (3) | C15—C16—C17—C12 | −0.4 (4) |
C4—O2—C7—C8 | −159.37 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5B···O1i | 0.92 (4) | 1.89 (4) | 2.805 (3) | 176 (4) |
O5—H5A···O3i | 0.74 (4) | 2.30 (4) | 3.033 (3) | 172 (4) |
N2—H2···O5 | 0.84 (2) | 2.14 (2) | 2.962 (3) | 164 (2) |
O1—H1···N1ii | 0.88 (3) | 2.42 (3) | 3.091 (2) | 133 (2) |
O1—H1···O4ii | 0.88 (3) | 1.95 (3) | 2.768 (2) | 153 (3) |
C17—H17···O4 | 0.93 | 2.44 | 2.757 (3) | 100 |
C13—H13···O5 | 0.93 | 2.56 | 3.476 (3) | 167 |
C10—H10···O5 | 0.93 | 2.50 | 3.312 (3) | 146 |
C2—H2A···O1iii | 0.93 | 2.54 | 3.443 (2) | 163 |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H18N2O4·H2O |
Mr | 332.35 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 9.924 (2), 11.936 (3), 14.890 (4) |
β (°) | 104.003 (4) |
V (Å3) | 1711.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.46 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.948, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9477, 3508, 2112 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.627 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.129, 1.00 |
No. of reflections | 3508 |
No. of parameters | 234 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.20 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5B···O1i | 0.92 (4) | 1.89 (4) | 2.805 (3) | 176 (4) |
O5—H5A···O3i | 0.74 (4) | 2.30 (4) | 3.033 (3) | 172 (4) |
N2—H2···O5 | 0.84 (2) | 2.14 (2) | 2.962 (3) | 164 (2) |
O1—H1···N1ii | 0.88 (3) | 2.42 (3) | 3.091 (2) | 133 (2) |
O1—H1···O4ii | 0.88 (3) | 1.95 (3) | 2.768 (2) | 153 (3) |
C17—H17···O4 | 0.93 | 2.44 | 2.757 (3) | 100 |
C13—H13···O5 | 0.93 | 2.56 | 3.476 (3) | 167 |
C10—H10···O5 | 0.93 | 2.50 | 3.312 (3) | 146 |
C2—H2A···O1iii | 0.93 | 2.54 | 3.443 (2) | 163 |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2. |
The synthesis of new and designed crystal structures has attracted attention in medicine and chemistry. One of the aims of crystal engineering is to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Tynan et al., 2005; Parashar et al., 1988). In the present study, we report the synthesis and molecular structure of the title compound, (I).
The bond lengths of O1—C8 and O2—C7 are 1.412 (2) and 1.430 (2) Å, respectively, and are normal. The bond length of N1—C10 is 1.269 Å and is similar to the value of 1.279 (3) Å in isonicotinic acid (2-hydroxy-3-methoxybenzylidene)hydrazide (Yu et al., 2005). The vanillin moiety (C1–C7/O2/O3) and the benzohydrazide moiety (C11–C17) are planar, with r.m.s. deviations of the fitted atoms of 0.0342 and 0.0085 Å, respectively. The hedral angle between the two planes mentioned above is 9.31 (11)°. It should be noted that the strong intramolecular and intermolecular hydrogen bonds are found in the crystal structure (Table 1). The intramolecular hydrogen bonds stabilize the comformation of molecule, while the intermolecular hydrogen bonds contribute to the stabilization of the solid state. At the same time, the lattice water molecule participates in interactions with the molecules through hydrogen bonds, stabilizing the zigzag suprastructure, as shown in Fig. 2.