(E)-N′-[(2-Hydroxy-1-naphthyl)methyl­ene]benzohydrazide monohydrate

Qiao, Y.; Ju, X.; Gao, Z.; Kong, L.

doi:10.1107/S160053680905212X

organic compounds

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Volume 66| Part 1| January 2010| Page o95

doi:10.1107/S160053680905212X

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(E)-N′-[(2-Hydroxy-1-naphthyl)methylene]benzohydrazide monohydrate

Yan Qiao,^a Xiuping Ju,^a Zhiqing Gao ^a and Lingqian Kong ^a ^*

^aDongchang College, Liaocheng University, Liaocheng, 250059, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 2 November 2009; accepted 3 December 2009; online 9 December 2009)

In the title compound, C₁₈H₁₄N₂O₂·H₂O, the dihedral angle between the benzene ring and the naphthalene system is 5.18 (10)°. Intramolecular N—H⋯O hydrogen bonds influence the molecular conformation. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds are observed as well as π–π interactions between the phenyl ring and the substituted ring of the naphthalene [centroid–centroid distance = 3.676 (11) Å].

Related literature

For background to Schiff bases in coordination chemistry, see: Chakraborty & Patel (1996 ); Jeewoth et al. (1999 ). For their biological activity, see: Das et al. (1999 ). For related structures, see: Fun et al.(2008 ); Nie (2008 ).

Experimental

Crystal data

C₁₈H₁₄N₂O₂·H₂O
M_r = 308.33
Monoclinic, P 2₁ /c
a = 16.346 (6) Å
b = 7.192 (3) Å
c = 13.880 (5) Å
β = 111.949 (4)°
V = 1513.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.48 × 0.43 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.955, T_max = 0.961
7296 measured reflections
2669 independent reflections
1648 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.148
S = 1.07
2669 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	2.11	2.899 (3)	152
O2—H2⋯N2	0.82	1.89	2.604 (3)	145
O3—H3C⋯O1ⁱ	0.85	2.03	2.882 (3)	179
O3—H3D⋯O1ⁱⁱ	0.85	1.88	2.734 (3)	179
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL .

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905212X/bq2175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905212X/bq2175Isup2.hkl

checkCIF report

Comment top

Schiff bases are popular ligands in coordination chemistry due to their ease of synthesis and their ability to be readily modified both electronically and sterically. (Chakraborty et al., 1996; Jeewoth et al., 1999). Meanwhile, aromatic aldehyde Schiff bases have also attracted much attention due to their diverse biological activities, such as antimicrobial antibacterial, antiviral, anticancer activities etc (Das et al., 1999).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in reported the compound (Nie et al., 2008; Fun et al., 2008).

In the crystal structure, the C=N bond length in the molecule is 1.282 (3) °, showing the double-bond character. Meanwhile, the dihedral angle between the benzene ring (C3—C8) and the naphthalene plane in the Schiff base molecule is 5.18 (10) °, indicating that the two planes are almost coplanar.

Moreover, there exist one H₂O molecule in the crystal unit, the crystal structure of the title compound consists of one two-dimension supramolecular structure was built from the connections of N—H···O, O—H..O hydrogen bonds and (Table 1.) two π···π stacking interactions between the rings (C2-C7) and (C9-C14) and their symmetry related counterparts (Symmetry code=-x+1, -y, -z+1 and centroid-to centroid distance = 3.676 (11) Å).

Related literature top

For background to Schiff bases in coordination chemistry, see: Chakraborty et al. (1996); Jeewoth et al. (1999). For their biological activity, see: Das et al. (1999). For related structures, see: Fun et al.(2008); Nie (2008).

Experimental top

2-Hydroxy-1-naphthaldehyde (3 mmol), benzohydrazide (3 mmol) and 10 ml methanol were mixed in 50 ml flask. After stirring 30 min at 373 K, the resulting mixture was recrystalized from methanol, affording the title compound as a colorless crystalline solid. Elemental analysis: calculated for C₁₈H₁₆N₂O₃: C 70.12, H 5.23, N 9.09%; found: C 70.18, H 5.15, N 9.14%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids, showing the intramolecular H-bond with dashed line.
	Fig. 2. A packing of (I) viewed down b-axis showing H-bond interactions with dashed lines. Symmetry codes: (i) -x, -y, -z+1; (ii) x, -y+1/2, z+1/2..
	Fig. 3. The π···π interactions of (I) with dashed lines. Symmetry codes: (A) -x+1, -y, -z+1.

(E)-N'-[(2-Hydroxy-1-naphthyl)methylene]benzohydrazide monohydrate top

Crystal data top

C₁₈H₁₄N₂O₂·H₂O	F(000) = 648
M_r = 308.33	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2137 reflections
a = 16.346 (6) Å	θ = 2.7–26.8°
b = 7.192 (3) Å	µ = 0.09 mm⁻¹
c = 13.880 (5) Å	T = 298 K
β = 111.949 (4)°	Block, colourless
V = 1513.5 (10) Å³	0.50 × 0.48 × 0.43 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2669 independent reflections
Radiation source: fine-focus sealed tube	1648 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→19
T_min = 0.955, T_max = 0.961	k = −8→8
7296 measured reflections	l = −16→13

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0594P)² + 0.5603P] where P = (F_o² + 2F_c²)/3
2669 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₁₄N₂O₂·H₂O	V = 1513.5 (10) Å³
M_r = 308.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.346 (6) Å	µ = 0.09 mm⁻¹
b = 7.192 (3) Å	T = 298 K
c = 13.880 (5) Å	0.50 × 0.48 × 0.43 mm
β = 111.949 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2669 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1648 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.961	R_int = 0.027
7296 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.07	Δρ_max = 0.25 e Å⁻³
2669 reflections	Δρ_min = −0.21 e Å⁻³
208 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

	x	y	z	U_iso*/U_eq
N1	0.03568 (12)	0.2307 (3)	0.50343 (16)	0.0462 (5)
H1	0.0334	0.2363	0.5643	0.055*
N2	0.11241 (12)	0.1782 (3)	0.49103 (16)	0.0482 (5)
O1	−0.03364 (11)	0.2630 (3)	0.33109 (14)	0.0679 (6)
O2	0.21163 (12)	0.1127 (3)	0.38534 (13)	0.0711 (6)
H2	0.1675	0.1496	0.3941	0.107*
O3	0.06076 (12)	0.1282 (3)	0.71458 (14)	0.0790 (6)
H3C	0.0524	0.0128	0.7015	0.095*
H3D	0.0312	0.1610	0.7507	0.095*
C1	−0.03525 (15)	0.2726 (3)	0.41878 (19)	0.0437 (6)
C2	−0.11669 (14)	0.3308 (3)	0.43458 (18)	0.0407 (6)
C3	−0.12564 (16)	0.3358 (4)	0.5298 (2)	0.0513 (6)
H3	−0.0784	0.3025	0.5897	0.062*
C4	−0.20439 (17)	0.3902 (4)	0.5361 (2)	0.0602 (7)
H4	−0.2100	0.3933	0.6003	0.072*
C5	−0.27411 (17)	0.4393 (4)	0.4486 (2)	0.0594 (7)
H5	−0.3271	0.4755	0.4534	0.071*
C6	−0.26626 (17)	0.4356 (4)	0.3545 (2)	0.0615 (7)
H6	−0.3140	0.4691	0.2951	0.074*
C7	−0.18785 (16)	0.3825 (3)	0.34665 (19)	0.0531 (6)
H7	−0.1827	0.3814	0.2821	0.064*
C8	0.17844 (15)	0.1408 (3)	0.5745 (2)	0.0466 (6)
H8	0.1727	0.1529	0.6384	0.056*
C9	0.26175 (14)	0.0802 (3)	0.57090 (18)	0.0412 (6)
C10	0.27378 (16)	0.0654 (3)	0.47759 (19)	0.0496 (6)
C11	0.35283 (17)	−0.0052 (4)	0.4732 (2)	0.0592 (7)
H11	0.3601	−0.0117	0.4100	0.071*
C12	0.41789 (17)	−0.0633 (4)	0.5610 (2)	0.0559 (7)
H12	0.4690	−0.1131	0.5568	0.067*
C13	0.41064 (15)	−0.0507 (3)	0.65878 (19)	0.0475 (6)
C14	0.33263 (14)	0.0262 (3)	0.66492 (18)	0.0422 (6)
C15	0.32900 (18)	0.0419 (4)	0.7644 (2)	0.0587 (7)
H15	0.2797	0.0953	0.7715	0.070*
C16	0.3967 (2)	−0.0201 (5)	0.8507 (2)	0.0741 (9)
H16	0.3927	−0.0077	0.9155	0.089*
C17	0.47164 (19)	−0.1017 (4)	0.8435 (2)	0.0724 (8)
H17	0.5164	−0.1468	0.9026	0.087*
C18	0.47854 (16)	−0.1145 (4)	0.7497 (2)	0.0603 (7)
H18	0.5290	−0.1665	0.7450	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0417 (11)	0.0484 (12)	0.0551 (12)	0.0012 (9)	0.0258 (10)	−0.0028 (10)
N2	0.0418 (12)	0.0468 (12)	0.0622 (14)	0.0010 (9)	0.0266 (10)	−0.0019 (10)
O1	0.0670 (12)	0.0933 (15)	0.0546 (11)	0.0107 (10)	0.0355 (10)	0.0084 (10)
O2	0.0629 (12)	0.0993 (16)	0.0516 (11)	0.0146 (11)	0.0218 (9)	0.0020 (11)
O3	0.0876 (15)	0.1016 (16)	0.0615 (12)	0.0114 (12)	0.0435 (11)	−0.0008 (12)
C1	0.0469 (14)	0.0405 (13)	0.0506 (15)	−0.0026 (11)	0.0261 (12)	0.0028 (11)
C2	0.0388 (13)	0.0358 (12)	0.0495 (14)	−0.0043 (10)	0.0189 (11)	−0.0012 (10)
C3	0.0439 (14)	0.0600 (16)	0.0530 (15)	0.0013 (12)	0.0215 (12)	0.0023 (13)
C4	0.0588 (17)	0.0674 (18)	0.0662 (17)	0.0024 (14)	0.0371 (14)	−0.0011 (15)
C5	0.0441 (15)	0.0564 (17)	0.083 (2)	0.0031 (12)	0.0301 (15)	−0.0041 (15)
C6	0.0449 (15)	0.0650 (18)	0.0677 (19)	0.0042 (13)	0.0131 (13)	0.0003 (15)
C7	0.0535 (15)	0.0539 (16)	0.0523 (15)	−0.0019 (12)	0.0203 (12)	−0.0010 (12)
C8	0.0460 (14)	0.0426 (14)	0.0575 (15)	−0.0036 (11)	0.0266 (12)	−0.0042 (12)
C9	0.0388 (13)	0.0376 (13)	0.0516 (14)	−0.0026 (10)	0.0219 (11)	−0.0042 (11)
C10	0.0451 (14)	0.0538 (15)	0.0523 (16)	−0.0010 (11)	0.0209 (12)	−0.0023 (12)
C11	0.0546 (16)	0.0729 (18)	0.0605 (17)	0.0019 (14)	0.0334 (14)	−0.0056 (14)
C12	0.0446 (15)	0.0598 (17)	0.0730 (19)	0.0016 (12)	0.0329 (14)	−0.0046 (14)
C13	0.0403 (13)	0.0417 (13)	0.0618 (16)	−0.0052 (11)	0.0206 (12)	−0.0011 (12)
C14	0.0409 (13)	0.0392 (13)	0.0513 (15)	−0.0075 (10)	0.0227 (11)	−0.0040 (11)
C15	0.0541 (16)	0.0702 (19)	0.0572 (17)	−0.0040 (13)	0.0271 (14)	−0.0011 (14)
C16	0.074 (2)	0.097 (2)	0.0544 (18)	−0.0059 (18)	0.0268 (16)	0.0034 (16)
C17	0.0600 (19)	0.081 (2)	0.0658 (19)	−0.0025 (16)	0.0115 (15)	0.0121 (17)
C18	0.0438 (15)	0.0566 (17)	0.0778 (19)	−0.0005 (13)	0.0197 (14)	0.0037 (15)

Geometric parameters (Å, º) top

N1—C1	1.341 (3)	C7—H7	0.9300
N1—N2	1.381 (2)	C8—C9	1.448 (3)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.282 (3)	C9—C10	1.385 (3)
O1—C1	1.229 (3)	C9—C14	1.437 (3)
O2—C10	1.347 (3)	C10—C11	1.410 (3)
O2—H2	0.8200	C11—C12	1.349 (3)
O3—H3C	0.8500	C11—H11	0.9301
O3—H3D	0.8501	C12—C13	1.409 (3)
C1—C2	1.488 (3)	C12—H12	0.9300
C2—C3	1.383 (3)	C13—C18	1.410 (3)
C2—C7	1.385 (3)	C13—C14	1.421 (3)
C3—C4	1.379 (3)	C14—C15	1.408 (3)
C3—H3	0.9300	C15—C16	1.367 (4)
C4—C5	1.365 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.395 (4)
C5—C6	1.361 (4)	C16—H16	0.9300
C5—H5	0.9301	C17—C18	1.352 (4)
C6—C7	1.380 (3)	C17—H17	0.9300
C6—H6	0.9301	C18—H18	0.9300

C1—N1—N2	118.7 (2)	C10—C9—C14	118.7 (2)
C1—N1—H1	120.6	C10—C9—C8	121.3 (2)
N2—N1—H1	120.6	C14—C9—C8	120.0 (2)
C8—N2—N1	116.2 (2)	O2—C10—C9	123.3 (2)
C10—O2—H2	109.5	O2—C10—C11	115.3 (2)
H3C—O3—H3D	108.4	C9—C10—C11	121.4 (2)
O1—C1—N1	121.6 (2)	C12—C11—C10	119.9 (2)
O1—C1—C2	120.9 (2)	C12—C11—H11	120.1
N1—C1—C2	117.5 (2)	C10—C11—H11	120.1
C3—C2—C7	118.7 (2)	C11—C12—C13	121.9 (2)
C3—C2—C1	124.6 (2)	C11—C12—H12	119.1
C7—C2—C1	116.6 (2)	C13—C12—H12	119.1
C4—C3—C2	120.2 (2)	C12—C13—C18	121.3 (2)
C4—C3—H3	119.9	C12—C13—C14	118.9 (2)
C2—C3—H3	119.9	C18—C13—C14	119.8 (2)
C5—C4—C3	120.4 (3)	C15—C14—C13	117.2 (2)
C5—C4—H4	119.8	C15—C14—C9	123.6 (2)
C3—C4—H4	119.8	C13—C14—C9	119.2 (2)
C6—C5—C4	120.1 (3)	C16—C15—C14	121.1 (3)
C6—C5—H5	119.9	C16—C15—H15	119.5
C4—C5—H5	119.9	C14—C15—H15	119.5
C5—C6—C7	120.3 (2)	C15—C16—C17	121.3 (3)
C5—C6—H6	119.8	C15—C16—H16	119.4
C7—C6—H6	119.8	C17—C16—H16	119.4
C6—C7—C2	120.2 (2)	C18—C17—C16	119.3 (3)
C6—C7—H7	119.9	C18—C17—H17	120.3
C2—C7—H7	119.9	C16—C17—H17	120.3
N2—C8—C9	121.1 (2)	C17—C18—C13	121.2 (3)
N2—C8—H8	119.4	C17—C18—H18	119.4
C9—C8—H8	119.4	C13—C18—H18	119.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	2.11	2.899 (3)	152
O2—H2···N2	0.82	1.89	2.604 (3)	145
O3—H3C···O1ⁱ	0.85	2.03	2.882 (3)	179
O3—H3D···O1ⁱⁱ	0.85	1.88	2.734 (3)	179

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₂·H₂O
M_r	308.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.346 (6), 7.192 (3), 13.880 (5)
β (°)	111.949 (4)
V (Å³)	1513.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.48 × 0.43

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	7296, 2669, 1648
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.148, 1.07
No. of reflections	2669
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	2.11	2.899 (3)	151.9
O2—H2···N2	0.82	1.89	2.604 (3)	145.3
O3—H3C···O1ⁱ	0.85	2.03	2.882 (3)	179.1
O3—H3D···O1ⁱⁱ	0.85	1.88	2.734 (3)	179.2

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2.

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

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