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The crystal structure of the title compound, C15H14N2O2·H2O, is in the keto tautomeric form and the configuration at the azomethine C=N double bond is E. The mol­ecule is non-planar, with a dihedral angle of 27.3 (1)° between the aromatic rings. The crystal structure is stabilized by extensive hydrogen bonding involving the water mol­ecule and hydrazone moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000799X/na1476sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010000799X/na1476Isup2.hkl
Contains datablock I

CCDC reference: 150351

Comment top

Aroylhydrazone compounds are being studied extensively because of the strong coordinating hydrazone group to form polynuclear complexes. As a continuation of our work on the synthesis and characterization of aroylhydrazone compounds (Fun et al., 1999, 1996, 1997; Lu et al., 1999; Shanmuga Sundara Raj et al., 1999a), we report the crystal structure of the title compound, (I). \sch

The molecule is non-planar with a dihedral angle of 27.3 (1)° between the aromatic rings. The N1—N2 and C9—O2 bond distances, which are consistent with those in the related compounds, p-methoxybenzaldehyde isonicotinoylhydrazone monohydrate (Shanmuga Sundara Raj et al., 1999a) and its dihydrate derivative (Fun et al., 1996), indicate that these bonds correspond to single and double bonds. Thus the molecule is in a keto tautomeric form. Also, the configuration at the azomethine N1—C8 double bond is E. The C1—O1 and O1—C2 bond lengths in the hydroxyphenyl moiety is consistent with those [1.432 (2) and 1.370 (1) Å, and 1.436 (2) and 1.367 (2) Å, respectively] in the above related compounds. The keto group is in the plane of the central hydrazone bridge.

The asymmetry of the exocyclic angles at C5 is small: C4—C5—C8 = 122.3 (2), C6—C5—C8 = 120.0 (2)°, while that at C2 is larger: C3—C2—O1 = 114.7 (2), C7—C2—O1 = 125.0 (2)° and similar to that found usually in anisoles being caused by the tendency the methoxy group has to be coplanar with the phenyl ring. Conjugation of oxygen with phenyl, which is responsible for this coplanarity (Domiano et al., 1979), also causes some shortening of the C2—O1 bond. Some asymmetry is observed also for the exocyclic angles at C10: C9—C10—C11 = 118.2 (2) and C9—C10—C15 = 122.0 (2)° probably caused by the contacts: H11···O2 = 2.72 and H15···N2 = 2.74 Å. The torsion angles, C4—C5—C8—N1 = 11.7 (4) and N2—C9—C10—C15 = −44.7 (3)°, respectively, indicates that the methoxyphenyl and phenyl substituents are in syn-periplanar and syn-clinal orientations with respect to the central hydrazone plane. The methoxyphenyl ring makes a dihedral angle of 16.4 (1)° with the hydrazone bridge and the phenyl ring is twisted by an angle of 43.1 (1)° with the plane of the central hydrazone linkage.

The water and hydrazone group are involved in N—H···O and O—H···O hydrogen bonds to form a two-dimensional network. The H1W atom is involved in a three-center hydrogen bond.

Experimental top

The synthesis of the compound was carried out by reaction of p-methoxybenzaldehyde and benzoylhydrazine in ethanol solution under reflux for 3 h. Single crystals were obtained by recrystallization from ethanol.

Refinement top

Collection of intensity data was as described by Shanmuga Sundara Raj et al. (1999).

The H atoms of the water molecule were refined isotropically while all the others were geometrically fixed and allowed to ride on the parent atoms to which they are attached.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
p-Methoxybenzaldehyde Benzoylhydrazone Monohydrate top
Crystal data top
C15H14N2O2·H2OF(000) = 576
Mr = 272.30Dx = 1.251 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.9398 (6) ÅCell parameters from 3248 reflections
b = 11.8595 (6) Åθ = 1.9–29.4°
c = 11.3972 (6) ŵ = 0.09 mm1
β = 116.389 (1)°T = 293 K
V = 1445.68 (13) Å3Slab, colourless
Z = 40.40 × 0.24 × 0.16 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
1704 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
Graphite monochromatorθmax = 29.3°, θmin = 1.9°
Detector resolution: 8.33 pixels mm-1h = 1614
ω scansk = 1216
10036 measured reflectionsl = 1415
3650 independent reflections
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)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0764P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
2833 reflectionsΔρmax = 0.23 e Å3
190 parametersΔρmin = 0.21 e Å3
2 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (3)
Crystal data top
C15H14N2O2·H2OV = 1445.68 (13) Å3
Mr = 272.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9398 (6) ŵ = 0.09 mm1
b = 11.8595 (6) ÅT = 293 K
c = 11.3972 (6) Å0.40 × 0.24 × 0.16 mm
β = 116.389 (1)°
Data collection top
Siemens SMART CCD area detector
diffractometer
1704 reflections with I > 2σ(I)
10036 measured reflectionsRint = 0.067
3650 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 0.93Δρmax = 0.23 e Å3
2833 reflectionsΔρmin = 0.21 e Å3
190 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.14877 (15)0.41833 (15)0.62626 (15)0.0673 (5)
O20.48621 (14)0.11530 (13)0.60664 (14)0.0546 (5)
N10.68145 (16)0.25838 (15)0.71384 (16)0.0444 (5)
N20.59483 (15)0.24386 (15)0.76335 (16)0.0440 (5)
H20.60130.28170.83050.053*
C11.2651 (2)0.4674 (3)0.7165 (3)0.0843 (9)
H1A1.31800.47750.67390.127*
H1B1.30560.41840.79060.127*
H1C1.24970.53920.74550.127*
C21.0620 (2)0.39819 (19)0.6718 (2)0.0489 (6)
C30.9541 (2)0.3440 (2)0.5833 (2)0.0590 (7)
H30.94480.32580.50010.071*
C40.8610 (2)0.3174 (2)0.6188 (2)0.0541 (6)
H40.78950.28040.55940.065*
C50.87257 (19)0.34513 (18)0.74243 (19)0.0425 (5)
C60.9807 (2)0.39945 (19)0.8279 (2)0.0524 (6)
H60.98990.41890.91070.063*
C71.0761 (2)0.4260 (2)0.7946 (2)0.0544 (6)
H71.14820.46190.85420.065*
C80.77408 (19)0.32161 (18)0.7817 (2)0.0454 (5)
H80.77910.35360.85840.054*
C90.50076 (19)0.16983 (18)0.7048 (2)0.0418 (5)
C100.4136 (2)0.15748 (17)0.7660 (2)0.0436 (5)
C110.2865 (2)0.1510 (2)0.6843 (2)0.0574 (6)
H110.25700.15570.59400.069*
C120.2038 (3)0.1375 (2)0.7380 (3)0.0721 (8)
H120.11830.13510.68360.087*
C130.2470 (3)0.1277 (2)0.8707 (3)0.0786 (9)
H130.19090.11800.90610.094*
C140.3720 (3)0.1324 (2)0.9509 (3)0.0830 (9)
H140.40120.12481.04100.100*
C150.4561 (2)0.1483 (2)0.8985 (2)0.0637 (7)
H150.54140.15270.95370.076*
O1W0.62976 (17)0.09820 (14)0.46274 (16)0.0563 (5)
H1W0.608 (3)0.120 (2)0.525 (2)0.093 (10)*
H2W0.590 (3)0.034 (2)0.430 (3)0.151 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0623 (10)0.0798 (12)0.0741 (12)0.0249 (9)0.0431 (9)0.0175 (10)
O20.0630 (10)0.0546 (9)0.0576 (10)0.0128 (8)0.0370 (8)0.0159 (8)
N10.0451 (10)0.0466 (11)0.0492 (11)0.0019 (9)0.0279 (9)0.0016 (9)
N20.0463 (10)0.0489 (11)0.0450 (10)0.0055 (9)0.0277 (8)0.0062 (9)
C10.0660 (17)0.094 (2)0.112 (2)0.0388 (16)0.0571 (17)0.0394 (18)
C20.0467 (13)0.0501 (13)0.0559 (14)0.0083 (11)0.0281 (11)0.0050 (11)
C30.0578 (14)0.0761 (17)0.0492 (14)0.0159 (13)0.0294 (12)0.0146 (12)
C40.0459 (13)0.0664 (16)0.0482 (14)0.0133 (12)0.0194 (11)0.0121 (12)
C50.0404 (12)0.0444 (12)0.0439 (12)0.0027 (10)0.0199 (10)0.0020 (10)
C60.0545 (14)0.0602 (15)0.0441 (13)0.0065 (12)0.0235 (11)0.0088 (11)
C70.0456 (13)0.0617 (15)0.0539 (14)0.0126 (11)0.0204 (11)0.0118 (12)
C80.0484 (13)0.0469 (12)0.0445 (12)0.0032 (11)0.0240 (10)0.0030 (10)
C90.0448 (12)0.0410 (12)0.0433 (12)0.0019 (10)0.0229 (10)0.0001 (10)
C100.0499 (13)0.0395 (12)0.0475 (13)0.0045 (10)0.0273 (11)0.0048 (10)
C110.0534 (14)0.0599 (15)0.0622 (15)0.0020 (12)0.0287 (12)0.0006 (12)
C120.0546 (15)0.0656 (18)0.106 (2)0.0037 (13)0.0442 (16)0.0031 (16)
C130.091 (2)0.0673 (18)0.115 (3)0.0282 (16)0.080 (2)0.0243 (17)
C140.112 (2)0.094 (2)0.0644 (17)0.0472 (19)0.0585 (18)0.0202 (16)
C150.0684 (16)0.0753 (17)0.0534 (15)0.0253 (14)0.0323 (13)0.0064 (13)
O1W0.0772 (12)0.0511 (10)0.0555 (10)0.0067 (9)0.0430 (9)0.0023 (8)
Geometric parameters (Å, º) top
O1—C21.371 (2)C6—C71.387 (3)
O1—C11.434 (3)C6—H60.9300
O2—C91.236 (2)C7—H70.9300
N1—C81.274 (3)C8—H80.9300
N1—N21.392 (2)C9—C101.495 (3)
N2—C91.346 (3)C10—C151.368 (3)
N2—H20.8600C10—C111.386 (3)
C1—H1A0.9600C11—C121.383 (3)
C1—H1B0.9600C11—H110.9300
C1—H1C0.9600C12—C131.369 (4)
C2—C71.373 (3)C12—H120.9300
C2—C31.391 (3)C13—C141.361 (4)
C3—C41.378 (3)C13—H130.9300
C3—H30.9300C14—C151.391 (3)
C4—C51.393 (3)C14—H140.9300
C4—H40.9300C15—H150.9300
C5—C61.383 (3)O1W—H1W0.895 (17)
C5—C81.459 (3)O1W—H2W0.890 (19)
C2—O1—C1117.0 (2)C2—C7—H7120.6
C8—N1—N2115.3 (2)C6—C7—H7120.6
C9—N2—N1119.1 (2)N1—C8—C5121.75 (19)
C9—N2—H2120.4N1—C8—H8119.1
N1—N2—H2120.4C5—C8—H8119.1
O1—C1—H1A109.5O2—C9—N2122.7 (2)
O1—C1—H1B109.5O2—C9—C10121.6 (2)
H1A—C1—H1B109.5N2—C9—C10115.7 (2)
O1—C1—H1C109.5C15—C10—C11119.7 (2)
H1A—C1—H1C109.5C15—C10—C9122.0 (2)
H1B—C1—H1C109.5C11—C10—C9118.30 (19)
O1—C2—C7125.0 (2)C12—C11—C10119.6 (2)
O1—C2—C3114.72 (19)C12—C11—H11120.2
C7—C2—C3120.3 (2)C10—C11—H11120.2
C4—C3—C2120.1 (2)C13—C12—C11120.4 (3)
C4—C3—H3120.0C13—C12—H12119.8
C2—C3—H3120.0C11—C12—H12119.8
C3—C4—C5120.8 (2)C14—C13—C12120.0 (2)
C3—C4—H4119.6C14—C13—H13120.0
C5—C4—H4119.6C12—C13—H13120.0
C6—C5—C4117.64 (19)C13—C14—C15120.2 (3)
C6—C5—C8120.03 (19)C13—C14—H14119.9
C4—C5—C8122.31 (19)C15—C14—H14119.9
C5—C6—C7122.4 (2)C10—C15—C14120.0 (2)
C5—C6—H6118.8C10—C15—H15120.0
C7—C6—H6118.8C14—C15—H15120.0
C2—C7—C6118.7 (2)H1W—O1W—H2W107 (3)
C8—N1—N2—C9173.6 (2)C4—C5—C8—N111.7 (3)
C1—O1—C2—C73.0 (3)N1—N2—C9—O21.5 (3)
C1—O1—C2—C3176.1 (2)N1—N2—C9—C10178.7 (2)
O1—C2—C3—C4178.8 (2)O2—C9—C10—C15135.4 (2)
C7—C2—C3—C40.4 (4)N2—C9—C10—C1544.7 (3)
C2—C3—C4—C50.7 (4)O2—C9—C10—C1142.1 (3)
C3—C4—C5—C60.4 (3)N2—C9—C10—C11137.8 (2)
C3—C4—C5—C8177.9 (2)C15—C10—C11—C121.3 (3)
C4—C5—C6—C70.3 (3)C9—C10—C11—C12178.8 (2)
C8—C5—C6—C7178.6 (2)C10—C11—C12—C131.6 (4)
O1—C2—C7—C6179.4 (2)C11—C12—C13—C140.6 (4)
C3—C2—C7—C60.3 (4)C12—C13—C14—C150.7 (4)
C5—C6—C7—C20.6 (4)C11—C10—C15—C140.1 (4)
N2—N1—C8—C5179.9 (2)C9—C10—C15—C14177.4 (2)
C6—C5—C8—N1170.0 (2)C13—C14—C15—C101.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···N10.90 (3)2.53 (2)3.257 (2)138 (3)
O1W—H1W···O20.90 (3)2.05 (4)2.858 (3)150 (3)
N2—H2···O1Wi0.861.992.829 (2)165
O1W—H2W···O2ii0.89 (3)1.95 (3)2.825 (2)169 (3)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC15H14N2O2·H2O
Mr272.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.9398 (6), 11.8595 (6), 11.3972 (6)
β (°) 116.389 (1)
V3)1445.68 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.24 × 0.16
Data collection
DiffractometerSiemens SMART CCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10036, 3650, 1704
Rint0.067
(sin θ/λ)max1)0.689
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.120, 0.93
No. of reflections2833
No. of parameters190
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O1—C21.371 (2)N1—N21.392 (2)
O1—C11.434 (3)N2—C91.346 (3)
O2—C91.236 (2)C5—C81.459 (3)
N1—C81.274 (3)C10—C151.368 (3)
C8—N1—N2115.3 (2)O2—C9—C10121.6 (2)
C9—N2—N1119.1 (2)N2—C9—C10115.7 (2)
O2—C9—N2122.7 (2)
C8—N1—N2—C9173.6 (2)N1—N2—C9—C10178.7 (2)
N2—N1—C8—C5179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···N10.90 (3)2.53 (2)3.257 (2)138 (3)
O1W—H1W···O20.90 (3)2.05 (4)2.858 (3)150 (3)
N2—H2···O1Wi0.861.992.829 (2)165
O1W—H2W···O2ii0.89 (3)1.95 (3)2.825 (2)169 (3)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z+1.
 

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