(E)-N′-[4-(Dimethyl­amino)­benzyl­idene]-4-hy­droxy­benzohydrazide hemihydrate

Liu, H.

doi:10.1107/S1600536810020763

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1582

doi:10.1107/S1600536810020763

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(E)-N′-[4-(Dimethylamino)benzylidene]-4-hydroxybenzohydrazide hemihydrate

Huanyu Liu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528453, People's Republic of China
^*Correspondence e-mail: liuhuanyu03@163.com

(Received 28 May 2010; accepted 31 May 2010; online 5 June 2010)

In the title compound, C₁₆H₁₇N₃O₂·0.5H₂O, the two hydrazide molecules are approximately planar: the dihedral angles between the two substituted benzene rings are 7.7 (2) and 4.2 (2)°. Both hydrazone molecules exist in a trans geometry with respect to their methylidene units. In the crystal, the water molecule lies between the two organic molecules and makes bifurcated O—H⋯(N,O) hydrogen bonds to both of them. The hydrazide molecules form N—H⋯O and O—H⋯O hydrogen bonds, resulting in a three-dimensional network.

Related literature

For the biological activity of hydrazone compounds, see: Banerjee et al. (2009 ). For the structures of hydrazone compounds, see: Ahmad et al. (2010 ); Li et al. (2010 ); Naveenkumar et al. (2010 ); Zhang (2009 ); Fun et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₂·0.5H₂O
M_r = 292.34
Monoclinic, P 2₁
a = 6.1514 (9) Å
b = 18.098 (3) Å
c = 13.356 (2) Å
β = 95.489 (2)°
V = 1480.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.28 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.976
8336 measured reflections
3254 independent reflections
2593 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.094
S = 1.04
3254 reflections
407 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5C⋯O2ⁱ	0.90 (1)	2.56 (3)	3.171 (3)	125 (3)
N2—H2A⋯O5ⁱⁱ	0.90 (1)	2.12 (1)	3.003 (3)	168 (3)
O4—H4⋯O1ⁱⁱⁱ	0.82	1.90	2.688 (2)	160
O2—H2B⋯O3^iv	0.82	1.89	2.693 (3)	166
O5—H5A⋯O3	0.85 (1)	2.43 (2)	3.178 (3)	146 (3)
O5—H5A⋯N4	0.85 (1)	2.34 (2)	3.038 (3)	140 (3)
O5—H5B⋯O1	0.85 (1)	2.36 (2)	3.100 (3)	145 (3)
O5—H5B⋯N1	0.85 (1)	2.61 (2)	3.375 (3)	150 (3)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) x-1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: 10.1107/S1600536810020763/hb5475sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020763/hb5475Isup2.hkl

checkCIF report

Comment top

In recent years, much attention has been focused on the biological properties of hydrazone compounds (e.g. Banerjee et al., 2009). A number of hydrazone compounds have been prepared and investigated for their structures (Ahmad et al., 2010; Li et al., 2010; Naveenkumar et al., 2010; Zhang, 2009; Fun et al., 2008). In the present work, a new hydrazone compound with interesting structure is reported.

The title compound consists of two hydrazone molecules and one water molecule (Fig. 1). The two hydrazone molecules are approximately parallel to each other, and are linked together by the water molecule through O—H···N and O—H···O hydrogen bonds (Table 1). Both hydrazone molecules exist in trans geometry with respect to the methylidene units. The dihedral angles between the two substituted benzene rings in the hydrazone molecules are 7.7 (2) and 4.2 (2)°.

In the crystal structure, the hydrazone molecules and the water molecules are linked through N—H···O, O—H···O and O—H···N hydrogen bonds (Table 1), forming a three dimensional network (Fig. 2).

Related literature top

For the biological activity of hydrazone compounds, see: Banerjee et al. (2009). For the structures of hydrazone compounds, see: Ahmad et al. (2010); Li et al. (2010); Naveenkumar et al. (2010); Zhang (2009); Fun et al. (2008).

Experimental top

4-Dimethylaminobenzaldehyde (1.0 mmol, 149 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152 mg) were mixed in 50 ml methanol. The mixture was stirred at ambient temperature for 2 h and filtered. Colorless blocks of (I) were formed by slow evaporation of the filtrate for a week; presumably water was incorporated from the atmosphere.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. Molecular structure of (I) with 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Packing structure of (I), viewed along the a axis. Hydrogen bonds are shown as dashed lines.

(E)-N'-[4-(Dimethylamino)benzylidene]-4-hydroxybenzohydrazide hemihydrate top

Crystal data top

C₁₆H₁₇N₃O₂·0.5H₂O	F(000) = 620
M_r = 292.34	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2665 reflections
a = 6.1514 (9) Å	θ = 2.6–24.5°
b = 18.098 (3) Å	µ = 0.09 mm⁻¹
c = 13.356 (2) Å	T = 298 K
β = 95.489 (2)°	Block, colorless
V = 1480.1 (4) Å³	0.28 × 0.27 × 0.27 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3254 independent reflections
Radiation source: fine-focus sealed tube	2593 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
T_min = 0.975, T_max = 0.976	k = −23→23
8336 measured reflections	l = −9→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0535P)² + 0.0137P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3254 reflections	Δρ_max = 0.13 e Å⁻³
407 parameters	Δρ_min = −0.11 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Crystal data top

C₁₆H₁₇N₃O₂·0.5H₂O	V = 1480.1 (4) Å³
M_r = 292.34	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.1514 (9) Å	µ = 0.09 mm⁻¹
b = 18.098 (3) Å	T = 298 K
c = 13.356 (2) Å	0.28 × 0.27 × 0.27 mm
β = 95.489 (2)°

Data collection top

Bruker SMART CCD diffractometer	3254 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2593 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.976	R_int = 0.028
8336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	6 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.13 e Å⁻³
3254 reflections	Δρ_min = −0.11 e Å⁻³
407 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.4602 (3)	0.17321 (13)	0.29539 (14)	0.0654 (6)
O2	0.0189 (3)	0.07939 (12)	0.68381 (15)	0.0651 (6)
H2B	0.1181	0.0548	0.7126	0.098*
O3	0.7089 (4)	0.48243 (11)	0.21582 (13)	0.0603 (5)
O4	0.3140 (3)	0.69296 (12)	−0.13484 (15)	0.0649 (6)
H4	0.4072	0.6910	−0.1747	0.097*
O5	0.7330 (3)	0.31729 (12)	0.2971 (2)	0.0688 (6)
N1	0.2364 (3)	0.27325 (12)	0.18320 (15)	0.0465 (5)
N2	0.1558 (4)	0.24130 (13)	0.26688 (16)	0.0486 (5)
N3	0.2760 (4)	0.48063 (14)	−0.21084 (17)	0.0611 (6)
N4	0.3944 (4)	0.43505 (13)	0.32898 (16)	0.0540 (6)
N5	0.3526 (4)	0.47696 (14)	0.24264 (17)	0.0565 (6)
N6	0.2273 (4)	0.26319 (14)	0.73893 (17)	0.0574 (6)
C1	0.2382 (5)	0.44061 (15)	−0.1264 (2)	0.0478 (6)
C2	0.3964 (4)	0.39311 (15)	−0.0790 (2)	0.0500 (6)
H2	0.5311	0.3887	−0.1047	0.060*
C3	0.3556 (4)	0.35288 (15)	0.0050 (2)	0.0496 (6)
H3	0.4637	0.3219	0.0349	0.059*
C4	0.1567 (4)	0.35769 (13)	0.04580 (19)	0.0423 (6)
C5	0.0014 (5)	0.40579 (16)	−0.0010 (2)	0.0523 (7)
H5	−0.1325	0.4106	0.0253	0.063*
C6	0.0391 (5)	0.44617 (15)	−0.0841 (2)	0.0540 (7)
H6	−0.0688	0.4777	−0.1130	0.065*
C7	0.4777 (6)	0.4754 (2)	−0.2563 (2)	0.0733 (9)
H7A	0.5724	0.5152	−0.2327	0.110*
H7B	0.4487	0.4785	−0.3281	0.110*
H7C	0.5468	0.4291	−0.2386	0.110*
C8	0.1119 (6)	0.5281 (2)	−0.2596 (3)	0.0777 (10)
H8A	−0.0102	0.4989	−0.2867	0.117*
H8B	0.1715	0.5544	−0.3131	0.117*
H8C	0.0646	0.5627	−0.2118	0.117*
C9	0.1034 (4)	0.31732 (14)	0.13410 (19)	0.0475 (6)
H9	−0.0343	0.3238	0.1560	0.057*
C10	0.2801 (4)	0.19211 (14)	0.32054 (19)	0.0446 (6)
C11	0.1976 (4)	0.16137 (13)	0.41294 (18)	0.0403 (5)
C12	0.3309 (4)	0.11208 (16)	0.4684 (2)	0.0518 (7)
H12	0.4620	0.0979	0.4449	0.062*
C13	0.2740 (5)	0.08319 (17)	0.5585 (2)	0.0537 (7)
H13	0.3663	0.0501	0.5949	0.064*
C14	0.0801 (5)	0.10396 (14)	0.59334 (19)	0.0486 (6)
C15	−0.0585 (5)	0.15106 (16)	0.5375 (2)	0.0548 (7)
H15	−0.1926	0.1634	0.5598	0.066*
C16	0.0001 (4)	0.18011 (15)	0.4486 (2)	0.0510 (6)
H16	−0.0937	0.2127	0.4120	0.061*
C17	0.2277 (4)	0.30157 (14)	0.65040 (19)	0.0442 (6)
C18	0.0467 (5)	0.34222 (16)	0.6109 (2)	0.0529 (7)
H18	−0.0778	0.3437	0.6452	0.063*
C19	0.0500 (5)	0.38022 (16)	0.5216 (2)	0.0565 (7)
H19	−0.0734	0.4064	0.4965	0.068*
C20	0.2329 (4)	0.38037 (14)	0.4682 (2)	0.0484 (6)
C21	0.4131 (4)	0.34006 (14)	0.5066 (2)	0.0485 (6)
H21	0.5370	0.3391	0.4718	0.058*
C22	0.4125 (4)	0.30143 (15)	0.5953 (2)	0.0490 (6)
H22	0.5359	0.2748	0.6193	0.059*
C23	0.0321 (5)	0.25746 (19)	0.7900 (2)	0.0673 (9)
H23A	−0.0182	0.3061	0.8051	0.101*
H23B	0.0634	0.2302	0.8514	0.101*
H23C	−0.0790	0.2323	0.7476	0.101*
C24	0.4155 (6)	0.2222 (2)	0.7789 (2)	0.0712 (9)
H24A	0.4520	0.1861	0.7304	0.107*
H24B	0.3842	0.1976	0.8395	0.107*
H24C	0.5364	0.2553	0.7933	0.107*
C25	0.2250 (5)	0.42193 (15)	0.3751 (2)	0.0546 (7)
H25	0.0908	0.4399	0.3476	0.065*
C26	0.5169 (5)	0.50093 (14)	0.19151 (19)	0.0473 (6)
C27	0.4562 (4)	0.55060 (13)	0.10541 (17)	0.0421 (6)
C28	0.2589 (4)	0.58769 (15)	0.09028 (19)	0.0503 (6)
H28	0.1542	0.5804	0.1351	0.060*
C29	0.2144 (4)	0.63495 (16)	0.0107 (2)	0.0517 (7)
H29	0.0806	0.6592	0.0021	0.062*
C30	0.3686 (4)	0.64671 (14)	−0.05740 (18)	0.0456 (6)
C31	0.5696 (4)	0.61128 (15)	−0.04239 (19)	0.0491 (6)
H31	0.6753	0.6193	−0.0865	0.059*
C32	0.6112 (4)	0.56435 (14)	0.03792 (19)	0.0462 (6)
H32	0.7464	0.5411	0.0476	0.055*
H2A	0.030 (3)	0.2603 (18)	0.284 (2)	0.080*
H5C	0.213 (2)	0.4898 (19)	0.223 (2)	0.080*
H5A	0.694 (5)	0.3625 (7)	0.297 (3)	0.080*
H5B	0.617 (3)	0.2919 (14)	0.285 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0554 (12)	0.0931 (15)	0.0510 (11)	0.0225 (11)	0.0224 (9)	0.0161 (11)
O2	0.0711 (14)	0.0726 (14)	0.0561 (12)	−0.0083 (11)	0.0306 (11)	0.0069 (10)
O3	0.0715 (14)	0.0634 (12)	0.0472 (11)	0.0164 (11)	0.0119 (10)	0.0052 (9)
O4	0.0611 (13)	0.0811 (14)	0.0558 (12)	0.0156 (11)	0.0230 (10)	0.0279 (11)
O5	0.0549 (12)	0.0606 (12)	0.0941 (16)	0.0071 (10)	0.0228 (12)	−0.0077 (12)
N1	0.0485 (13)	0.0501 (11)	0.0426 (12)	−0.0022 (10)	0.0124 (10)	0.0019 (10)
N2	0.0461 (12)	0.0555 (12)	0.0461 (12)	0.0021 (11)	0.0149 (10)	0.0063 (10)
N3	0.0613 (16)	0.0686 (15)	0.0532 (15)	−0.0010 (12)	0.0045 (12)	0.0180 (13)
N4	0.0742 (17)	0.0493 (12)	0.0392 (12)	−0.0003 (11)	0.0093 (11)	0.0065 (10)
N5	0.0670 (15)	0.0566 (13)	0.0470 (13)	0.0007 (12)	0.0109 (12)	0.0151 (11)
N6	0.0596 (15)	0.0673 (15)	0.0471 (13)	−0.0063 (12)	0.0153 (11)	0.0144 (12)
C1	0.0507 (16)	0.0488 (14)	0.0429 (14)	−0.0061 (12)	−0.0004 (12)	−0.0005 (12)
C2	0.0466 (15)	0.0570 (15)	0.0470 (15)	−0.0005 (13)	0.0070 (12)	0.0040 (13)
C3	0.0486 (15)	0.0507 (14)	0.0495 (15)	0.0032 (12)	0.0052 (13)	0.0044 (12)
C4	0.0421 (14)	0.0442 (13)	0.0407 (13)	0.0021 (11)	0.0041 (11)	0.0012 (11)
C5	0.0446 (15)	0.0592 (16)	0.0539 (16)	0.0081 (12)	0.0076 (12)	0.0011 (13)
C6	0.0537 (17)	0.0557 (16)	0.0520 (16)	0.0112 (13)	0.0017 (14)	0.0067 (13)
C7	0.081 (2)	0.082 (2)	0.0582 (19)	−0.0092 (19)	0.0156 (17)	0.0109 (17)
C8	0.083 (2)	0.080 (2)	0.068 (2)	0.0059 (19)	−0.0020 (18)	0.0280 (18)
C9	0.0431 (14)	0.0523 (14)	0.0479 (15)	0.0009 (12)	0.0084 (12)	−0.0007 (12)
C10	0.0447 (15)	0.0486 (14)	0.0416 (14)	−0.0001 (11)	0.0102 (11)	−0.0040 (11)
C11	0.0405 (13)	0.0415 (12)	0.0398 (13)	0.0002 (10)	0.0073 (11)	−0.0042 (10)
C12	0.0474 (15)	0.0624 (16)	0.0477 (15)	0.0042 (13)	0.0155 (12)	−0.0019 (13)
C13	0.0568 (17)	0.0601 (16)	0.0460 (14)	0.0065 (13)	0.0135 (13)	0.0075 (13)
C14	0.0553 (16)	0.0485 (14)	0.0440 (14)	−0.0101 (13)	0.0154 (12)	−0.0038 (12)
C15	0.0459 (15)	0.0631 (17)	0.0582 (17)	−0.0015 (14)	0.0196 (13)	−0.0019 (14)
C16	0.0466 (15)	0.0539 (15)	0.0540 (15)	−0.0003 (12)	0.0116 (12)	−0.0015 (13)
C17	0.0456 (14)	0.0443 (12)	0.0429 (14)	−0.0077 (11)	0.0054 (11)	0.0036 (11)
C18	0.0466 (16)	0.0582 (16)	0.0561 (16)	−0.0023 (13)	0.0165 (13)	0.0041 (14)
C19	0.0514 (17)	0.0561 (16)	0.0626 (18)	0.0050 (13)	0.0087 (14)	0.0123 (14)
C20	0.0573 (17)	0.0447 (13)	0.0442 (15)	−0.0021 (12)	0.0103 (13)	0.0045 (12)
C21	0.0513 (16)	0.0502 (14)	0.0463 (14)	−0.0049 (12)	0.0165 (12)	0.0013 (12)
C22	0.0466 (15)	0.0527 (14)	0.0485 (15)	0.0020 (12)	0.0095 (12)	0.0061 (12)
C23	0.075 (2)	0.075 (2)	0.0553 (17)	−0.0181 (17)	0.0228 (16)	0.0084 (16)
C24	0.086 (2)	0.074 (2)	0.0537 (18)	0.0081 (18)	0.0090 (17)	0.0218 (16)
C25	0.0645 (19)	0.0485 (15)	0.0511 (17)	0.0020 (13)	0.0079 (14)	0.0081 (13)
C26	0.0670 (19)	0.0406 (13)	0.0351 (13)	0.0054 (12)	0.0090 (13)	−0.0043 (11)
C27	0.0557 (15)	0.0371 (12)	0.0349 (12)	0.0009 (11)	0.0109 (11)	−0.0040 (10)
C28	0.0543 (16)	0.0564 (15)	0.0431 (14)	−0.0005 (13)	0.0198 (12)	0.0027 (12)
C29	0.0468 (15)	0.0615 (16)	0.0490 (16)	0.0078 (12)	0.0165 (12)	0.0070 (13)
C30	0.0527 (15)	0.0495 (14)	0.0368 (13)	0.0015 (12)	0.0158 (11)	0.0041 (11)
C31	0.0488 (15)	0.0559 (15)	0.0453 (15)	0.0045 (12)	0.0191 (12)	0.0020 (12)
C32	0.0505 (16)	0.0465 (14)	0.0428 (14)	0.0080 (11)	0.0103 (12)	0.0010 (11)

Geometric parameters (Å, º) top

O1—C10	1.236 (3)	C10—C11	1.487 (3)
O2—C14	1.373 (3)	C11—C12	1.379 (4)
O2—H2B	0.8200	C11—C16	1.388 (3)
O3—C26	1.240 (3)	C12—C13	1.387 (4)
O4—C30	1.348 (3)	C12—H12	0.9300
O4—H4	0.8200	C13—C14	1.374 (4)
O5—H5A	0.852 (10)	C13—H13	0.9300
O5—H5B	0.853 (10)	C14—C15	1.374 (4)
N1—C9	1.278 (3)	C15—C16	1.378 (4)
N1—N2	1.391 (3)	C15—H15	0.9300
N2—C10	1.337 (3)	C16—H16	0.9300
N2—H2A	0.896 (10)	C17—C18	1.396 (4)
N3—C1	1.379 (3)	C17—C22	1.412 (3)
N3—C8	1.434 (4)	C18—C19	1.379 (4)
N3—C7	1.436 (4)	C18—H18	0.9300
N4—C25	1.283 (4)	C19—C20	1.389 (4)
N4—N5	1.384 (3)	C19—H19	0.9300
N5—C26	1.345 (3)	C20—C21	1.384 (4)
N5—H5C	0.903 (10)	C20—C25	1.449 (4)
N6—C17	1.371 (3)	C21—C22	1.375 (4)
N6—C24	1.435 (4)	C21—H21	0.9300
N6—C23	1.441 (3)	C22—H22	0.9300
C1—C6	1.400 (4)	C23—H23A	0.9600
C1—C2	1.403 (4)	C23—H23B	0.9600
C2—C3	1.380 (4)	C23—H23C	0.9600
C2—H2	0.9300	C24—H24A	0.9600
C3—C4	1.389 (4)	C24—H24B	0.9600
C3—H3	0.9300	C24—H24C	0.9600
C4—C5	1.395 (4)	C25—H25	0.9300
C4—C9	1.451 (4)	C26—C27	1.479 (4)
C5—C6	1.368 (4)	C27—C28	1.385 (4)
C5—H5	0.9300	C27—C32	1.396 (3)
C6—H6	0.9300	C28—C29	1.372 (4)
C7—H7A	0.9600	C28—H28	0.9300
C7—H7B	0.9600	C29—C30	1.391 (3)
C7—H7C	0.9600	C29—H29	0.9300
C8—H8A	0.9600	C30—C31	1.390 (4)
C8—H8B	0.9600	C31—C32	1.373 (4)
C8—H8C	0.9600	C31—H31	0.9300
C9—H9	0.9300	C32—H32	0.9300

C14—O2—H2B	109.5	O2—C14—C15	118.1 (2)
C30—O4—H4	109.5	C13—C14—C15	120.0 (2)
H5A—O5—H5B	107 (2)	C14—C15—C16	120.3 (3)
C9—N1—N2	114.3 (2)	C14—C15—H15	119.9
C10—N2—N1	118.5 (2)	C16—C15—H15	119.9
C10—N2—H2A	126 (2)	C15—C16—C11	120.8 (3)
N1—N2—H2A	115 (2)	C15—C16—H16	119.6
C1—N3—C8	121.3 (3)	C11—C16—H16	119.6
C1—N3—C7	122.1 (3)	N6—C17—C18	121.7 (2)
C8—N3—C7	116.5 (3)	N6—C17—C22	121.1 (2)
C25—N4—N5	114.0 (2)	C18—C17—C22	117.2 (2)
C26—N5—N4	120.7 (2)	C19—C18—C17	120.8 (2)
C26—N5—H5C	120 (2)	C19—C18—H18	119.6
N4—N5—H5C	119 (2)	C17—C18—H18	119.6
C17—N6—C24	121.0 (2)	C18—C19—C20	121.7 (3)
C17—N6—C23	121.0 (2)	C18—C19—H19	119.2
C24—N6—C23	117.8 (2)	C20—C19—H19	119.2
N3—C1—C6	121.0 (3)	C21—C20—C19	117.9 (2)
N3—C1—C2	121.8 (3)	C21—C20—C25	123.5 (2)
C6—C1—C2	117.3 (2)	C19—C20—C25	118.6 (3)
C3—C2—C1	121.2 (3)	C22—C21—C20	121.3 (2)
C3—C2—H2	119.4	C22—C21—H21	119.3
C1—C2—H2	119.4	C20—C21—H21	119.3
C2—C3—C4	121.4 (2)	C21—C22—C17	121.1 (2)
C2—C3—H3	119.3	C21—C22—H22	119.5
C4—C3—H3	119.3	C17—C22—H22	119.5
C3—C4—C5	117.0 (2)	N6—C23—H23A	109.5
C3—C4—C9	124.3 (2)	N6—C23—H23B	109.5
C5—C4—C9	118.7 (2)	H23A—C23—H23B	109.5
C6—C5—C4	122.4 (3)	N6—C23—H23C	109.5
C6—C5—H5	118.8	H23A—C23—H23C	109.5
C4—C5—H5	118.8	H23B—C23—H23C	109.5
C5—C6—C1	120.8 (3)	N6—C24—H24A	109.5
C5—C6—H6	119.6	N6—C24—H24B	109.5
C1—C6—H6	119.6	H24A—C24—H24B	109.5
N3—C7—H7A	109.5	N6—C24—H24C	109.5
N3—C7—H7B	109.5	H24A—C24—H24C	109.5
H7A—C7—H7B	109.5	H24B—C24—H24C	109.5
N3—C7—H7C	109.5	N4—C25—C20	123.1 (3)
H7A—C7—H7C	109.5	N4—C25—H25	118.5
H7B—C7—H7C	109.5	C20—C25—H25	118.5
N3—C8—H8A	109.5	O3—C26—N5	121.5 (2)
N3—C8—H8B	109.5	O3—C26—C27	122.1 (2)
H8A—C8—H8B	109.5	N5—C26—C27	116.4 (2)
N3—C8—H8C	109.5	C28—C27—C32	117.6 (2)
H8A—C8—H8C	109.5	C28—C27—C26	124.1 (2)
H8B—C8—H8C	109.5	C32—C27—C26	118.2 (2)
N1—C9—C4	123.2 (2)	C29—C28—C27	121.5 (2)
N1—C9—H9	118.4	C29—C28—H28	119.2
C4—C9—H9	118.4	C27—C28—H28	119.2
O1—C10—N2	121.4 (2)	C28—C29—C30	120.3 (2)
O1—C10—C11	120.5 (2)	C28—C29—H29	119.9
N2—C10—C11	118.1 (2)	C30—C29—H29	119.9
C12—C11—C16	117.9 (2)	O4—C30—C31	123.4 (2)
C12—C11—C10	117.1 (2)	O4—C30—C29	117.5 (2)
C16—C11—C10	124.9 (2)	C31—C30—C29	119.2 (2)
C11—C12—C13	121.6 (3)	C32—C31—C30	119.7 (2)
C11—C12—H12	119.2	C32—C31—H31	120.2
C13—C12—H12	119.2	C30—C31—H31	120.2
C14—C13—C12	119.3 (3)	C31—C32—C27	121.8 (2)
C14—C13—H13	120.3	C31—C32—H32	119.1
C12—C13—H13	120.3	C27—C32—H32	119.1
O2—C14—C13	122.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5C···O2ⁱ	0.90 (1)	2.56 (3)	3.171 (3)	125 (3)
N2—H2A···O5ⁱⁱ	0.90 (1)	2.12 (1)	3.003 (3)	168 (3)
O4—H4···O1ⁱⁱⁱ	0.82	1.90	2.688 (2)	160
O2—H2B···O3^iv	0.82	1.89	2.693 (3)	166
O5—H5A···O3	0.85 (1)	2.43 (2)	3.178 (3)	146 (3)
O5—H5A···N4	0.85 (1)	2.34 (2)	3.038 (3)	140 (3)
O5—H5B···O1	0.85 (1)	2.36 (2)	3.100 (3)	145 (3)
O5—H5B···N1	0.85 (1)	2.61 (2)	3.375 (3)	150 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₂·0.5H₂O
M_r	292.34
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	6.1514 (9), 18.098 (3), 13.356 (2)
β (°)	95.489 (2)
V (Å³)	1480.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	8336, 3254, 2593
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.04
No. of reflections	3254
No. of parameters	407
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.11

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
N5—H5C···O2ⁱ	0.903 (10)	2.56 (3)	3.171 (3)	125 (3)
N2—H2A···O5ⁱⁱ	0.896 (10)	2.120 (13)	3.003 (3)	168 (3)
O4—H4···O1ⁱⁱⁱ	0.82	1.90	2.688 (2)	160
O2—H2B···O3^iv	0.82	1.89	2.693 (3)	166
O5—H5A···O3	0.852 (10)	2.43 (2)	3.178 (3)	146 (3)
O5—H5A···N4	0.852 (10)	2.34 (2)	3.038 (3)	140 (3)
O5—H5B···O1	0.853 (10)	2.364 (19)	3.100 (3)	145 (3)
O5—H5B···N1	0.853 (10)	2.611 (19)	3.375 (3)	150 (3)

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

Acknowledgements

The work was supported by the Guangdong Pharmaceutical University Young Teachers' Fund and the Ten Hundred Thousand Project of the Bureau of Education of Guangdong Province, China.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976. Web of Science CrossRef IUCr Journals Google Scholar
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Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S. & Kalluraya, B. (2008). Acta Cryst. E64, o1907–o1908. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, C., Wang, P. & Su, Y.-Q. (2010). Acta Cryst. E66, o520. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o1337–o1338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, X. (2009). Acta Cryst. E65, o2200. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Page o1582

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-[4-(Di­methyl­amino)­benzyl­­idene]-4-hy­dr­oxy­benzohydrazide hemihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-[4-(Dimethylamino)benzylidene]-4-hydroxybenzohydrazide hemihydrate