Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044443/pv2031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044443/pv2031Isup2.hkl |
CCDC reference: 663782
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.123
- Data-to-parameter ratio = 11.1
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general backgroud, see: Sun et al. (2006); Gup & Kirkan (2005); Ganjali et al. (2006); Getautis et al. (2006); Kuriakose et al. (2007); Owen & Wenbin (2002); Tobin (1990). For related literature, see: (Allen et al. (1987); Yathirajan et al. (2007); Mathew et al. (2007); Sun et al. (2007); Dance (1996).
For the preparation of the title compound, a mixture of 2-hydroxy-2,2-diphenylacetohydrazide (240 mg, 1 mmol) and furan-2-carbaldehyde (110 mg, 1.1 mmol) dissolved in propanol (25 ml), was refluxed with stirring for 3 h. The resulting mixture was filtered off and allowed to stand undisturbed at room temperature. The title compound crystallized out during few days as colourless plates. Crystals were filtered off, washed with 20 ml cold methanol then 10 ml diethylether, and dried under vacuum (yield: 89%). Solid; mp 451–452 K; Spectroscopic analysis: IR (KBr, ν cm-1): 3280; νNH, 1667; νC=O, 1625; νC=N; 1H NMR (300 MHz, DMSO, δ, p.p.m.): 3.50 (s, OH); 9.9 (s, CONH); 9.30 (s,CH=); 7.10 - 7.40 (m, ArH); 7.70–7.90 (m, R); EIMS: m/z = 320 (M+).
All H atoms were located in the difference map and refined independently with isotropic thermal displacement coefficients.
Schiff base hydrazones derived from the condensation of aromatic carbaldehydes and hydrazides are of interest owing to their biological activities and applications (Sun et al., 2006; Gup & Kirkan, 2005; Ganjali et al., 2006; Getautis et al., 2006). They have been also used as multidentate ligands for complexation with metal ions (Kuriakose et al., 2007). On the other hand, research in the field of supramolecular complexes containing metal ions and aroylhdrazones is of a considerable interest due to their possible applications as molecule-based metals and magnets, optical and thermal switches, and probes for DNA structurs (Owen & Wenbin, 2002; Tobin, 1990). The crystal structure of the title compound is reported here.
The asymmetric unit of the title compound comprises an organic moiety and a water of solvation (Fig. 1). Bond distances and angles, are within normal ranges (Allen et al., 1987), and in accordance with those reported for similar compounds (Yathirajan et al., 2007; Mathew et al., 2007; Sun et al., 2007). The existance of organic moiety in the title compound in the expected keto form is evident from the C6—O2 bond length, and the C5=N1 bond length confirms the double bond character. The C6–N2 bond length is typical for an intermediate between a single and a double bond, suggesting some degree of delocalization in the hydrazide.
The molecules are packed efficiently in a layer motif running parallel to the c axis, Fig. 2. In this arrangement, the molecules are linked to each other by water molecules that involve in multihydrogen bonding with the organic moiety. Its two H atoms engage each in binding to one O and one N atoms simultyaneouly (Fig. 1) as O—H···N, O—H···O and O—H···O, forming a double bifurcated hydrogen bonds. The water molecules further interact with the OH groups from the next organic molecule parallel to c axis (Fig. 2). These hydrogen bonds are extremely strong (Table 1) as is evident by relatively short D···A distances and D—H···A angles. There is a strong intramolecular interaction N2—H2A···O3 in the structure. In addition to the hydrogen bonding, molecules within layers exhibit via phenyl···phenyl (Ph···Ph) interactions (Dance 1996) in an edge-to-face ef motif (C—H···π; C12—H12···C17, C18 (x, 1/2 - y, 1/2 + z) of the order of 2.969 and 2.978 Å, respectively). The Ph···Ph interactions, using the diphenyl groups, between each layer and the adjacent one parallel to the a axis also exist comprising both offset-to-face (off) and edge-to-face (ef) motifs (C···C distances in the range 3.9 - 4.1 Å), Fig. 2.
Ph···Ph interactions together with the extremely strong hydrogen bonds contribute greatly in stabilization of a three-dimensional network.
For general backgroud, see: Sun et al. (2006); Gup & Kirkan (2005); Ganjali et al. (2006); Getautis et al. (2006); Kuriakose et al. (2007); Owen & Wenbin (2002); Tobin (1990). For related literature, see: (Allen et al. (1987); Yathirajan et al. (2007); Mathew et al. (2007); Sun et al. (2007); Dance (1996).
Data collection: CAD-4 (Enraf–Nonius, 1994); cell refinement: SET4 and CELDIM (Enraf–Nonius, 1994); data reduction: HELENA (Spek, 1996) and PLATON (Spek, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 1997b).
C19H16N2O3·H2O | F(000) = 712 |
Mr = 338.35 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 10.6339 (17) Å | θ = 2.1–27.4° |
b = 10.857 (2) Å | µ = 0.10 mm−1 |
c = 14.5207 (12) Å | T = 213 K |
β = 91.819 (10)° | Plate, colorless |
V = 1675.6 (4) Å3 | 0.55 × 0.50 × 0.20 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1981 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.054 |
Graphite monochromator | θmax = 26.1°, θmin = 3.1° |
ω scans | h = −1→13 |
Absorption correction: ψ scan (program; reference?) | k = 0→13 |
Tmin = 0.937, Tmax = 0.985 | l = −17→17 |
3847 measured reflections | 3 standard reflections every 400 reflections |
3293 independent reflections | intensity decay: 3.0% |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0534P)2 + 0.0604P] where P = (Fo2 + 2Fc2)/3 |
3293 reflections | (Δ/σ)max < 0.001 |
298 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C19H16N2O3·H2O | V = 1675.6 (4) Å3 |
Mr = 338.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.6339 (17) Å | µ = 0.10 mm−1 |
b = 10.857 (2) Å | T = 213 K |
c = 14.5207 (12) Å | 0.55 × 0.50 × 0.20 mm |
β = 91.819 (10)° |
Enraf–Nonius CAD-4 diffractometer | 1981 reflections with I > 2σ(I) |
Absorption correction: ψ scan (program; reference?) | Rint = 0.054 |
Tmin = 0.937, Tmax = 0.985 | 3 standard reflections every 400 reflections |
3847 measured reflections | intensity decay: 3.0% |
3293 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.123 | All H-atom parameters refined |
S = 1.01 | Δρmax = 0.17 e Å−3 |
3293 reflections | Δρmin = −0.20 e Å−3 |
298 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 | ||
C1 | 1.1720 (2) | 0.2889 (2) | 0.13010 (15) | 0.0332 (5) | |
O1 | 1.14268 (15) | 0.18466 (15) | 0.07977 (11) | 0.0413 (4) | |
C4 | 1.2148 (3) | 0.1898 (3) | 0.00285 (17) | 0.0436 (6) | |
H4 | 1.201 (2) | 0.116 (3) | −0.0400 (18) | 0.058 (8)* | |
C3 | 1.2863 (3) | 0.2907 (3) | 0.00473 (17) | 0.0444 (6) | |
H3 | 1.346 (2) | 0.316 (2) | −0.0402 (19) | 0.058 (8)* | |
C2 | 1.2589 (2) | 0.3555 (3) | 0.08660 (18) | 0.0413 (6) | |
H2 | 1.288 (2) | 0.432 (3) | 0.1031 (18) | 0.053 (8)* | |
C5 | 1.1047 (2) | 0.3121 (2) | 0.21232 (16) | 0.0346 (5) | |
H5 | 1.124 (2) | 0.390 (2) | 0.2423 (15) | 0.038 (6)* | |
N1 | 1.02022 (17) | 0.23747 (18) | 0.23979 (12) | 0.0347 (5) | |
N2 | 0.95604 (18) | 0.2774 (2) | 0.31553 (13) | 0.0341 (5) | |
H2A | 0.978 (2) | 0.347 (2) | 0.3437 (16) | 0.037 (7)* | |
O2 | 0.81756 (15) | 0.11956 (15) | 0.30338 (11) | 0.0408 (4) | |
C6 | 0.8530 (2) | 0.2155 (2) | 0.34018 (14) | 0.0311 (5) | |
C7 | 0.7808 (2) | 0.2756 (2) | 0.41943 (15) | 0.0330 (5) | |
O3 | 0.85302 (15) | 0.38056 (15) | 0.44913 (12) | 0.0368 (4) | |
H3A | 0.851 (3) | 0.390 (3) | 0.512 (2) | 0.084 (11)* | |
C8 | 0.7711 (2) | 0.1843 (2) | 0.49953 (14) | 0.0336 (5) | |
C9 | 0.8780 (3) | 0.1208 (2) | 0.52946 (17) | 0.0413 (6) | |
H9 | 0.955 (2) | 0.130 (2) | 0.4964 (17) | 0.049 (7)* | |
C10 | 0.8751 (3) | 0.0443 (2) | 0.60630 (17) | 0.0472 (7) | |
H10 | 0.953 (3) | −0.001 (3) | 0.6239 (18) | 0.055 (8)* | |
C11 | 0.7665 (3) | 0.0320 (3) | 0.65384 (18) | 0.0526 (8) | |
H11 | 0.762 (2) | −0.023 (2) | 0.708 (2) | 0.061 (8)* | |
C12 | 0.6610 (3) | 0.0944 (3) | 0.6250 (2) | 0.0588 (8) | |
H12 | 0.584 (3) | 0.088 (3) | 0.652 (2) | 0.070 (9)* | |
C13 | 0.6619 (3) | 0.1708 (3) | 0.54799 (18) | 0.0480 (7) | |
H13 | 0.586 (2) | 0.213 (2) | 0.5267 (18) | 0.053 (8)* | |
C14 | 0.6519 (2) | 0.3186 (2) | 0.38027 (14) | 0.0331 (5) | |
C19 | 0.5693 (2) | 0.2389 (3) | 0.33438 (17) | 0.0425 (6) | |
H19 | 0.593 (2) | 0.155 (3) | 0.3246 (18) | 0.048 (8)* | |
C18 | 0.4533 (3) | 0.2802 (3) | 0.30040 (19) | 0.0504 (7) | |
H18 | 0.400 (3) | 0.226 (2) | 0.2699 (18) | 0.054 (8)* | |
C17 | 0.4181 (3) | 0.4014 (3) | 0.31322 (19) | 0.0520 (8) | |
H17 | 0.340 (3) | 0.429 (3) | 0.2918 (18) | 0.059 (8)* | |
C16 | 0.4982 (3) | 0.4808 (3) | 0.3585 (2) | 0.0538 (7) | |
H16 | 0.474 (3) | 0.568 (3) | 0.3693 (19) | 0.063 (8)* | |
C15 | 0.6151 (3) | 0.4395 (3) | 0.39158 (18) | 0.0456 (7) | |
H15 | 0.669 (3) | 0.496 (2) | 0.4232 (19) | 0.055 (8)* | |
O4 | 0.9139 (2) | 0.03785 (18) | 0.12617 (13) | 0.0501 (5) | |
H4" | 0.892 (4) | 0.079 (4) | 0.174 (3) | 0.137 (18)* | |
H4' | 0.997 (4) | 0.071 (4) | 0.116 (3) | 0.123 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0347 (13) | 0.0348 (13) | 0.0300 (12) | 0.0010 (11) | 0.0006 (10) | −0.0048 (11) |
O1 | 0.0487 (10) | 0.0379 (9) | 0.0380 (9) | −0.0019 (8) | 0.0098 (8) | −0.0047 (8) |
C4 | 0.0563 (16) | 0.0442 (15) | 0.0309 (13) | 0.0065 (14) | 0.0097 (12) | −0.0021 (12) |
C3 | 0.0478 (15) | 0.0518 (17) | 0.0343 (13) | 0.0051 (14) | 0.0122 (12) | 0.0069 (13) |
C2 | 0.0453 (16) | 0.0393 (15) | 0.0398 (15) | −0.0069 (12) | 0.0072 (12) | −0.0003 (12) |
C5 | 0.0348 (13) | 0.0373 (14) | 0.0318 (12) | −0.0024 (12) | 0.0018 (10) | −0.0052 (11) |
N1 | 0.0372 (11) | 0.0400 (11) | 0.0270 (10) | 0.0027 (9) | 0.0053 (8) | −0.0032 (9) |
N2 | 0.0386 (11) | 0.0366 (11) | 0.0276 (10) | −0.0036 (10) | 0.0070 (8) | −0.0069 (9) |
O2 | 0.0500 (10) | 0.0373 (10) | 0.0357 (9) | −0.0073 (8) | 0.0091 (8) | −0.0073 (8) |
C6 | 0.0359 (13) | 0.0333 (13) | 0.0241 (11) | −0.0002 (11) | −0.0002 (9) | 0.0003 (10) |
C7 | 0.0370 (13) | 0.0336 (13) | 0.0284 (12) | −0.0031 (11) | 0.0011 (10) | −0.0039 (10) |
O3 | 0.0439 (10) | 0.0381 (9) | 0.0285 (9) | −0.0079 (8) | 0.0031 (8) | −0.0063 (8) |
C8 | 0.0405 (13) | 0.0373 (13) | 0.0230 (11) | −0.0031 (11) | 0.0017 (10) | −0.0040 (10) |
C9 | 0.0421 (15) | 0.0484 (16) | 0.0332 (13) | −0.0046 (13) | −0.0023 (12) | −0.0016 (12) |
C10 | 0.0601 (18) | 0.0457 (16) | 0.0353 (14) | −0.0015 (15) | −0.0073 (13) | 0.0006 (12) |
C11 | 0.081 (2) | 0.0479 (17) | 0.0291 (14) | −0.0066 (16) | 0.0059 (14) | 0.0025 (13) |
C12 | 0.065 (2) | 0.069 (2) | 0.0439 (17) | −0.0013 (17) | 0.0223 (15) | 0.0081 (15) |
C13 | 0.0477 (16) | 0.0589 (18) | 0.0380 (14) | 0.0064 (14) | 0.0117 (13) | 0.0048 (13) |
C14 | 0.0365 (12) | 0.0414 (14) | 0.0216 (11) | −0.0010 (11) | 0.0056 (10) | 0.0013 (10) |
C19 | 0.0415 (15) | 0.0479 (17) | 0.0380 (14) | −0.0075 (13) | −0.0017 (11) | 0.0000 (12) |
C18 | 0.0396 (15) | 0.069 (2) | 0.0418 (15) | −0.0119 (15) | −0.0047 (12) | 0.0025 (15) |
C17 | 0.0400 (16) | 0.077 (2) | 0.0396 (15) | 0.0099 (16) | 0.0021 (13) | 0.0074 (15) |
C16 | 0.0537 (18) | 0.057 (2) | 0.0507 (16) | 0.0158 (15) | 0.0037 (14) | −0.0042 (15) |
C15 | 0.0490 (16) | 0.0456 (16) | 0.0421 (14) | 0.0016 (14) | −0.0013 (13) | −0.0090 (13) |
O4 | 0.0717 (14) | 0.0477 (12) | 0.0309 (10) | −0.0153 (10) | 0.0000 (9) | −0.0013 (9) |
C1—C2 | 1.347 (3) | C9—C10 | 1.392 (4) |
C1—O1 | 1.377 (3) | C9—H9 | 0.97 (3) |
C1—C5 | 1.434 (3) | C10—C11 | 1.370 (4) |
O1—C4 | 1.376 (3) | C10—H10 | 0.99 (3) |
C4—C3 | 1.333 (4) | C11—C12 | 1.365 (4) |
C4—H4 | 1.02 (3) | C11—H11 | 0.98 (3) |
C3—C2 | 1.420 (4) | C12—C13 | 1.393 (4) |
C3—H3 | 0.96 (3) | C12—H12 | 0.92 (3) |
C2—H2 | 0.91 (3) | C13—H13 | 0.97 (3) |
C5—N1 | 1.282 (3) | C14—C15 | 1.381 (3) |
C5—H5 | 0.97 (2) | C14—C19 | 1.389 (3) |
N1—N2 | 1.382 (3) | C19—C18 | 1.388 (4) |
N2—C6 | 1.343 (3) | C19—H19 | 0.95 (3) |
N2—H2A | 0.89 (2) | C18—C17 | 1.381 (4) |
O2—C6 | 1.225 (3) | C18—H18 | 0.92 (3) |
C6—C7 | 1.548 (3) | C17—C16 | 1.366 (4) |
C7—O3 | 1.433 (3) | C17—H17 | 0.93 (3) |
C7—C8 | 1.534 (3) | C16—C15 | 1.392 (4) |
C7—C14 | 1.539 (3) | C16—H16 | 1.00 (3) |
O3—H3A | 0.92 (3) | C15—H15 | 0.94 (3) |
C8—C13 | 1.384 (3) | O4—H4" | 0.86 (5) |
C8—C9 | 1.388 (3) | O4—H4' | 0.97 (5) |
C2—C1—O1 | 109.8 (2) | C8—C9—H9 | 119.6 (15) |
C2—C1—C5 | 131.6 (2) | C10—C9—H9 | 119.8 (15) |
O1—C1—C5 | 118.4 (2) | C11—C10—C9 | 120.2 (3) |
C4—O1—C1 | 105.93 (19) | C11—C10—H10 | 122.2 (15) |
C3—C4—O1 | 110.4 (2) | C9—C10—H10 | 117.7 (16) |
C3—C4—H4 | 136.8 (15) | C12—C11—C10 | 119.6 (3) |
O1—C4—H4 | 112.8 (15) | C12—C11—H11 | 118.8 (16) |
C4—C3—C2 | 107.0 (2) | C10—C11—H11 | 121.5 (16) |
C4—C3—H3 | 127.2 (16) | C11—C12—C13 | 121.0 (3) |
C2—C3—H3 | 125.8 (16) | C11—C12—H12 | 124.2 (19) |
C1—C2—C3 | 106.8 (2) | C13—C12—H12 | 114.7 (19) |
C1—C2—H2 | 126.6 (17) | C8—C13—C12 | 119.9 (3) |
C3—C2—H2 | 126.3 (17) | C8—C13—H13 | 119.2 (16) |
N1—C5—C1 | 121.4 (2) | C12—C13—H13 | 120.9 (16) |
N1—C5—H5 | 123.4 (14) | C15—C14—C19 | 118.2 (2) |
C1—C5—H5 | 115.0 (14) | C15—C14—C7 | 119.8 (2) |
C5—N1—N2 | 114.69 (19) | C19—C14—C7 | 122.0 (2) |
C6—N2—N1 | 118.8 (2) | C18—C19—C14 | 120.7 (3) |
C6—N2—H2A | 120.6 (16) | C18—C19—H19 | 119.2 (16) |
N1—N2—H2A | 120.3 (16) | C14—C19—H19 | 120.1 (16) |
O2—C6—N2 | 123.5 (2) | C17—C18—C19 | 120.1 (3) |
O2—C6—C7 | 122.0 (2) | C17—C18—H18 | 120.7 (17) |
N2—C6—C7 | 114.5 (2) | C19—C18—H18 | 119.2 (17) |
O3—C7—C8 | 109.50 (17) | C16—C17—C18 | 119.9 (3) |
O3—C7—C14 | 109.42 (18) | C16—C17—H17 | 119.7 (17) |
C8—C7—C14 | 113.30 (18) | C18—C17—H17 | 120.4 (17) |
O3—C7—C6 | 106.54 (18) | C17—C16—C15 | 120.0 (3) |
C8—C7—C6 | 109.77 (18) | C17—C16—H16 | 120.9 (16) |
C14—C7—C6 | 108.08 (17) | C15—C16—H16 | 119.2 (16) |
C7—O3—H3A | 111 (2) | C14—C15—C16 | 121.2 (3) |
C13—C8—C9 | 118.7 (2) | C14—C15—H15 | 120.0 (16) |
C13—C8—C7 | 122.1 (2) | C16—C15—H15 | 118.8 (16) |
C9—C8—C7 | 119.0 (2) | H4"—O4—H4' | 102 (4) |
C8—C9—C10 | 120.6 (3) | ||
C2—C1—O1—C4 | −0.3 (3) | C6—C7—C8—C9 | 47.0 (3) |
C5—C1—O1—C4 | 176.3 (2) | C13—C8—C9—C10 | 0.5 (4) |
C1—O1—C4—C3 | 0.5 (3) | C7—C8—C9—C10 | 175.1 (2) |
O1—C4—C3—C2 | −0.5 (3) | C8—C9—C10—C11 | −0.6 (4) |
O1—C1—C2—C3 | 0.0 (3) | C9—C10—C11—C12 | 0.5 (4) |
C5—C1—C2—C3 | −176.0 (2) | C10—C11—C12—C13 | −0.1 (4) |
C4—C3—C2—C1 | 0.4 (3) | C9—C8—C13—C12 | −0.1 (4) |
C2—C1—C5—N1 | 176.7 (3) | C7—C8—C13—C12 | −174.6 (2) |
O1—C1—C5—N1 | 1.0 (3) | C11—C12—C13—C8 | −0.1 (4) |
C1—C5—N1—N2 | −174.7 (2) | O3—C7—C14—C15 | −10.3 (3) |
C5—N1—N2—C6 | 169.5 (2) | C8—C7—C14—C15 | 112.2 (2) |
N1—N2—C6—O2 | 5.7 (3) | C6—C7—C14—C15 | −125.9 (2) |
N1—N2—C6—C7 | −174.00 (18) | O3—C7—C14—C19 | 170.6 (2) |
O2—C6—C7—O3 | 176.32 (19) | C8—C7—C14—C19 | −66.9 (3) |
N2—C6—C7—O3 | −4.0 (3) | C6—C7—C14—C19 | 55.0 (3) |
O2—C6—C7—C8 | 57.9 (3) | C15—C14—C19—C18 | 0.4 (4) |
N2—C6—C7—C8 | −122.5 (2) | C7—C14—C19—C18 | 179.5 (2) |
O2—C6—C7—C14 | −66.2 (3) | C14—C19—C18—C17 | −1.0 (4) |
N2—C6—C7—C14 | 113.5 (2) | C19—C18—C17—C16 | 0.7 (4) |
O3—C7—C8—C13 | 104.8 (2) | C18—C17—C16—C15 | 0.1 (4) |
C14—C7—C8—C13 | −17.6 (3) | C19—C14—C15—C16 | 0.4 (4) |
C6—C7—C8—C13 | −138.6 (2) | C7—C14—C15—C16 | −178.8 (2) |
O3—C7—C8—C9 | −69.7 (3) | C17—C16—C15—C14 | −0.6 (4) |
C14—C7—C8—C9 | 167.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O4i | 0.89 (2) | 2.40 (2) | 3.248 (3) | 159 (2) |
O3—H3A···O4ii | 0.92 (3) | 1.94 (3) | 2.776 (2) | 151 (3) |
O4—H4′′···O2 | 0.86 (5) | 2.11 (5) | 2.937 (3) | 161 (4) |
O4—H4′′···N1 | 0.86 (5) | 2.38 (5) | 2.929 (3) | 122 (4) |
O4—H4′···O1 | 0.97 (5) | 2.07 (5) | 3.003 (3) | 163 (4) |
O4—H4′···N1 | 0.97 (5) | 2.56 (5) | 2.929 (3) | 103 (4) |
N2—H2A···O3 | 0.89 (2) | 2.09 (2) | 2.521 (3) | 109 (2) |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H16N2O3·H2O |
Mr | 338.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 213 |
a, b, c (Å) | 10.6339 (17), 10.857 (2), 14.5207 (12) |
β (°) | 91.819 (10) |
V (Å3) | 1675.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.55 × 0.50 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (program; reference?) |
Tmin, Tmax | 0.937, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3847, 3293, 1981 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.123, 1.01 |
No. of reflections | 3293 |
No. of parameters | 298 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.17, −0.20 |
Computer programs: CAD-4 (Enraf–Nonius, 1994), SET4 and CELDIM (Enraf–Nonius, 1994), HELENA (Spek, 1996) and PLATON (Spek, 2003), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), PLATON (Spek, 2003), XCIF in SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O4i | 0.89 (2) | 2.40 (2) | 3.248 (3) | 159 (2) |
O3—H3A···O4ii | 0.92 (3) | 1.94 (3) | 2.776 (2) | 151 (3) |
O4—H4''···O2 | 0.86 (5) | 2.11 (5) | 2.937 (3) | 161 (4) |
O4—H4''···N1 | 0.86 (5) | 2.38 (5) | 2.929 (3) | 122 (4) |
O4—H4'···O1 | 0.97 (5) | 2.07 (5) | 3.003 (3) | 163 (4) |
O4—H4'···N1 | 0.97 (5) | 2.56 (5) | 2.929 (3) | 103 (4) |
N2—H2A···O3 | 0.89 (2) | 2.09 (2) | 2.521 (3) | 109 (2) |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |
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Schiff base hydrazones derived from the condensation of aromatic carbaldehydes and hydrazides are of interest owing to their biological activities and applications (Sun et al., 2006; Gup & Kirkan, 2005; Ganjali et al., 2006; Getautis et al., 2006). They have been also used as multidentate ligands for complexation with metal ions (Kuriakose et al., 2007). On the other hand, research in the field of supramolecular complexes containing metal ions and aroylhdrazones is of a considerable interest due to their possible applications as molecule-based metals and magnets, optical and thermal switches, and probes for DNA structurs (Owen & Wenbin, 2002; Tobin, 1990). The crystal structure of the title compound is reported here.
The asymmetric unit of the title compound comprises an organic moiety and a water of solvation (Fig. 1). Bond distances and angles, are within normal ranges (Allen et al., 1987), and in accordance with those reported for similar compounds (Yathirajan et al., 2007; Mathew et al., 2007; Sun et al., 2007). The existance of organic moiety in the title compound in the expected keto form is evident from the C6—O2 bond length, and the C5=N1 bond length confirms the double bond character. The C6–N2 bond length is typical for an intermediate between a single and a double bond, suggesting some degree of delocalization in the hydrazide.
The molecules are packed efficiently in a layer motif running parallel to the c axis, Fig. 2. In this arrangement, the molecules are linked to each other by water molecules that involve in multihydrogen bonding with the organic moiety. Its two H atoms engage each in binding to one O and one N atoms simultyaneouly (Fig. 1) as O—H···N, O—H···O and O—H···O, forming a double bifurcated hydrogen bonds. The water molecules further interact with the OH groups from the next organic molecule parallel to c axis (Fig. 2). These hydrogen bonds are extremely strong (Table 1) as is evident by relatively short D···A distances and D—H···A angles. There is a strong intramolecular interaction N2—H2A···O3 in the structure. In addition to the hydrogen bonding, molecules within layers exhibit via phenyl···phenyl (Ph···Ph) interactions (Dance 1996) in an edge-to-face ef motif (C—H···π; C12—H12···C17, C18 (x, 1/2 - y, 1/2 + z) of the order of 2.969 and 2.978 Å, respectively). The Ph···Ph interactions, using the diphenyl groups, between each layer and the adjacent one parallel to the a axis also exist comprising both offset-to-face (off) and edge-to-face (ef) motifs (C···C distances in the range 3.9 - 4.1 Å), Fig. 2.
Ph···Ph interactions together with the extremely strong hydrogen bonds contribute greatly in stabilization of a three-dimensional network.