(E)-N′-(4-Eth­oxy­benzyl­idene)-4-hy­droxy­benzohydrazide dihydrate

Fun, H.-K.; Horkaew, J.; Chantrapromma, S.; Karalai, C.

doi:10.1107/S1600536812019356

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1655-o1656

doi:10.1107/S1600536812019356

Open

access

(E)-N′-(4-Ethoxybenzylidene)-4-hydroxybenzohydrazide dihydrate

Hoong-Kun Fun,^a ^*‡ Jirapa Horkaew,^b Suchada Chantrapromma ^b § and Chatchanok Karalai ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 27 April 2012; accepted 30 April 2012; online 5 May 2012)

The benzohydrazide molecule of the title compound, C₁₆H₁₆N₂O₃·2H₂O, exists in a trans conformation with respect to the C=N double bond. The central O=C—NH—N=C plane [r.m.s. deviation of 0.0165 (1) Å for the five non-H atoms] makes dihedral angles of 6.04 (8) and 2.38 (8)°, respectively, with the hydroxy- and ethoxy-substituted benzene rings. The dihedral angle between these benzene rings is 3.82 (7)°. The ethoxy group is almost coplanar with the attached benzene ring with a C—O—C—C torsion angle of −176.58 (11)°. In the crystal, the benzohydrazide and water molecules are linked by N—H⋯O, O—H⋯O , O—H⋯N and C—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2011 ); Horkaew et al. (2011 , 2012 ). For applications of benzohydrazides, see: Loncle et al. (2004 ); Molyneux (2004 ); Promdet et al. (2011 ); Raj et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₃·2H₂O
M_r = 320.34
Monoclinic, P 2₁ /c
a = 7.1655 (1) Å
b = 17.3895 (3) Å
c = 13.6202 (2) Å
β = 110.875 (1)°
V = 1585.74 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.29 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.971, T_max = 0.984
22228 measured reflections
5737 independent reflections
4310 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.155
S = 1.03
5737 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1ⁱ	0.84	1.77	2.6106 (15)	174
N1—H2⋯O1Wⁱⁱ	0.85	2.10	2.9278 (16)	167
O1W—H3⋯O2ⁱⁱⁱ	0.81	2.06	2.8683 (15)	177
O1W—H4⋯O2W	0.88	1.84	2.7159 (19)	169
O2W—H5⋯O1^iv	0.87	2.14	2.8558 (18)	139
O2W—H5⋯N2^iv	0.87	2.55	3.3363 (19)	151
O2W—H6⋯O3^v	0.89	2.11	2.9791 (17)	165
C6—H6A⋯O1Wⁱⁱ	0.95	2.36	3.2942 (18)	169
C8—H8A⋯O1Wⁱⁱ	0.95	2.49	3.3222 (18)	146
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019356/is5130sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019356/is5130Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019356/is5130Isup3.cml

checkCIF report

Comment top

It has been known that a majority of benzohydrazides possesses various biological properties, such as antibacterial and antifungal (Loncle et al., 2004), and antiproliferative (Raj et al., 2007) activities. The title benzohydrazide derivative (I) was synthesized as part of our study on the bioactivity of benzohydrazide derivatives (Fun et al., 2011; Horkaew et al., 2011, 2012; Promdet et al., 2011) and was evaluated for antioxidant activity by DPPH scavenging (Molyneux, 2004). It was found to be active. Herein we report the synthesis and crystal structure of (I).

The title compound (Fig. 1), C₁₆H₁₆N₂O₃.2H₂O, comprises one benzohydrazide molecule and two water molecules. The molecule of benzohydrazide exists in a trans-configuration with respect to the C8═N2 bond and the torsion angle N1—N2—C8—C9 = -179.90 (11)° with the dihedral angle between the two benzene rings being 3.82 (7)°. The middle fragment are planar with an r.m.s. deviation of 0.0165 (1) Å for the five non-H atoms (O1, C7, N1, N2 and C8). The mean plane through this middle fragment makes the dihedral angles of 6.04 (8) and 2.38 (8)° with the 4-hydroxyphenyl and 4-ethoxyphenyl rings, respectively. The ethoxy group is co-planar with the bound benzene ring with the torsion angle C12—O3—C15—C16 = -176.58 (11)°. The molecule is therefore approximately planar. The two water molecules are linked to each other by an O—H···O hydrogen bond (Fig. 1). Bond distances of benzohydrazide are of normal values (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Horkaew et al., 2011, 2012).

In the crystal packing (Fig. 2), the molecules of benzohydrazide and water are linked by N—H···O, O—H···O, O—H···N and C—H···O hydrogen bonds (Table 1) into a three-dimensional network.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2011); Horkaew et al. (2011, 2012). For applications of benzohydrazides, see: Loncle et al. (2004); Molyneux (2004); Promdet et al. (2011); Raj et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound (I) was prepared by dissolving 4-hydroxybenzohydrazide (2 mmol, 0.30 g) in ethanol (15 ml). A solution of 4-ethoxybenzaldehyde (2 mmol, 0.27 ml) in ethanol (15 ml) was then added slowly to the reaction. The mixture was refluxed for around 6 hr. The solution was then cooled to room temperature and a white solid appeared. Colorless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from a methanol solution by slow evaporation of the solvent at room temperature after several days (m.p. 373-374 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 60% probability displacement ellipsoids and the atom-numbering scheme. The O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.

(E)-N'-(4-Ethoxybenzylidene)-4-hydroxybenzohydrazide dihydrate top

Crystal data top

C₁₆H₁₆N₂O₃·2H₂O	F(000) = 680
M_r = 320.34	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 373–374 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1655 (1) Å	Cell parameters from 5737 reflections
b = 17.3895 (3) Å	θ = 2.0–32.5°
c = 13.6202 (2) Å	µ = 0.10 mm⁻¹
β = 110.875 (1)°	T = 100 K
V = 1585.74 (4) Å³	Block, colorless
Z = 4	0.29 × 0.16 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5737 independent reflections
Radiation source: sealed tube	4310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 32.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.971, T_max = 0.984	k = −26→19
22228 measured reflections	l = −20→18

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0735P)² + 0.7894P] where P = (F_o² + 2F_c²)/3
5737 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃·2H₂O	V = 1585.74 (4) Å³
M_r = 320.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1655 (1) Å	µ = 0.10 mm⁻¹
b = 17.3895 (3) Å	T = 100 K
c = 13.6202 (2) Å	0.29 × 0.16 × 0.16 mm
β = 110.875 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5737 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4310 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.984	R_int = 0.032
22228 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.03	Δρ_max = 0.73 e Å⁻³
5737 reflections	Δρ_min = −0.28 e Å⁻³
209 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	0.75546 (15)	0.81977 (6)	0.40609 (8)	0.0174 (2)
O2	0.60182 (15)	0.81464 (6)	−0.08291 (8)	0.0188 (2)
H1	0.6435	0.7704	−0.0894	0.028*
O3	0.85596 (15)	1.15548 (6)	0.90045 (8)	0.0198 (2)
N1	0.70782 (16)	0.94655 (7)	0.37373 (9)	0.0146 (2)
H2	0.6729	0.9842	0.3315	0.018*
N2	0.75068 (16)	0.96088 (7)	0.47938 (9)	0.0151 (2)
C1	0.67580 (17)	0.86049 (7)	0.22842 (10)	0.0130 (2)
C2	0.67471 (19)	0.78444 (8)	0.19463 (11)	0.0156 (2)
H2A	0.6925	0.7437	0.2436	0.019*
C3	0.64817 (19)	0.76747 (8)	0.09099 (11)	0.0162 (2)
H3A	0.6461	0.7155	0.0690	0.019*
C4	0.62471 (18)	0.82718 (8)	0.01968 (10)	0.0145 (2)
C5	0.62192 (19)	0.90311 (8)	0.05149 (11)	0.0163 (2)
H5A	0.6018	0.9436	0.0020	0.020*
C6	0.64847 (19)	0.91980 (8)	0.15534 (11)	0.0156 (2)
H6A	0.6481	0.9718	0.1768	0.019*
C7	0.71456 (17)	0.87382 (7)	0.34201 (10)	0.0127 (2)
C8	0.73020 (19)	1.03161 (8)	0.50069 (11)	0.0162 (2)
H8A	0.6885	1.0676	0.4446	0.019*
C9	0.76804 (19)	1.05918 (8)	0.60712 (11)	0.0155 (2)
C10	0.8108 (2)	1.01088 (8)	0.69423 (11)	0.0200 (3)
H10A	0.8197	0.9569	0.6858	0.024*
C11	0.8404 (2)	1.04100 (8)	0.79300 (11)	0.0201 (3)
H11A	0.8681	1.0077	0.8517	0.024*
C12	0.82933 (18)	1.12032 (8)	0.80608 (11)	0.0166 (2)
C13	0.7880 (2)	1.16903 (8)	0.72028 (11)	0.0186 (3)
H13A	0.7809	1.2230	0.7291	0.022*
C14	0.7570 (2)	1.13863 (8)	0.62170 (11)	0.0189 (3)
H14A	0.7279	1.1721	0.5631	0.023*
C15	0.9043 (2)	1.10800 (9)	0.99250 (11)	0.0196 (3)
H15A	1.0348	1.0825	1.0066	0.024*
H15B	0.8012	1.0678	0.9820	0.024*
C16	0.9131 (2)	1.15890 (9)	1.08336 (11)	0.0207 (3)
H16A	0.9521	1.1283	1.1479	0.031*
H16B	0.7815	1.1818	1.0702	0.031*
H16C	1.0116	1.1998	1.0912	0.031*
O1W	0.36756 (19)	0.59100 (6)	0.24443 (9)	0.0301 (3)
H3	0.4370	0.6177	0.2921	0.045*
H4	0.2664	0.6197	0.2059	0.045*
O2W	0.0731 (2)	0.67607 (8)	0.10548 (11)	0.0471 (4)
H5	−0.0331	0.6558	0.0590	0.071*
H6	0.0705	0.7267	0.0963	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0255 (5)	0.0134 (5)	0.0125 (4)	−0.0004 (3)	0.0059 (4)	0.0019 (4)
O2	0.0281 (5)	0.0179 (5)	0.0100 (4)	0.0064 (4)	0.0062 (4)	−0.0004 (4)
O3	0.0277 (5)	0.0181 (5)	0.0126 (5)	0.0025 (4)	0.0059 (4)	−0.0014 (4)
N1	0.0212 (5)	0.0134 (5)	0.0086 (5)	0.0002 (4)	0.0047 (4)	0.0005 (4)
N2	0.0184 (5)	0.0170 (5)	0.0097 (5)	−0.0007 (4)	0.0044 (4)	−0.0015 (4)
C1	0.0142 (5)	0.0133 (6)	0.0111 (5)	0.0001 (4)	0.0041 (4)	−0.0003 (4)
C2	0.0220 (6)	0.0125 (6)	0.0129 (6)	0.0000 (4)	0.0067 (5)	0.0008 (5)
C3	0.0223 (6)	0.0132 (6)	0.0132 (6)	0.0008 (4)	0.0063 (5)	−0.0010 (5)
C4	0.0159 (5)	0.0165 (6)	0.0103 (6)	0.0025 (4)	0.0037 (4)	0.0000 (4)
C5	0.0227 (6)	0.0142 (6)	0.0123 (6)	0.0039 (4)	0.0067 (5)	0.0025 (5)
C6	0.0211 (5)	0.0129 (6)	0.0134 (6)	0.0024 (4)	0.0070 (5)	0.0012 (5)
C7	0.0137 (5)	0.0139 (6)	0.0105 (5)	−0.0006 (4)	0.0042 (4)	0.0000 (4)
C8	0.0203 (5)	0.0161 (6)	0.0125 (6)	−0.0015 (4)	0.0061 (5)	−0.0004 (5)
C9	0.0173 (5)	0.0176 (6)	0.0117 (6)	−0.0005 (4)	0.0052 (4)	−0.0018 (5)
C10	0.0275 (6)	0.0163 (6)	0.0162 (7)	0.0028 (5)	0.0078 (5)	0.0004 (5)
C11	0.0274 (6)	0.0175 (6)	0.0140 (6)	0.0030 (5)	0.0055 (5)	0.0020 (5)
C12	0.0166 (5)	0.0184 (6)	0.0139 (6)	−0.0005 (4)	0.0043 (5)	−0.0032 (5)
C13	0.0246 (6)	0.0145 (6)	0.0168 (7)	0.0002 (5)	0.0075 (5)	−0.0005 (5)
C14	0.0247 (6)	0.0154 (6)	0.0169 (6)	−0.0012 (5)	0.0080 (5)	−0.0005 (5)
C15	0.0236 (6)	0.0212 (7)	0.0144 (6)	0.0014 (5)	0.0073 (5)	0.0014 (5)
C16	0.0235 (6)	0.0247 (7)	0.0137 (6)	−0.0009 (5)	0.0066 (5)	−0.0027 (5)
O1W	0.0463 (7)	0.0148 (5)	0.0187 (6)	0.0027 (5)	−0.0014 (5)	−0.0031 (4)
O2W	0.0469 (8)	0.0341 (8)	0.0342 (8)	0.0181 (6)	−0.0176 (6)	−0.0151 (6)

Geometric parameters (Å, º) top

O1—C7	1.2445 (16)	C8—H8A	0.9500
O2—C4	1.3651 (16)	C9—C10	1.3957 (19)
O2—H1	0.8415	C9—C14	1.402 (2)
O3—C12	1.3738 (16)	C10—C11	1.388 (2)
O3—C15	1.4368 (17)	C10—H10A	0.9500
N1—C7	1.3428 (17)	C11—C12	1.397 (2)
N1—N2	1.3828 (15)	C11—H11A	0.9500
N1—H2	0.8479	C12—C13	1.387 (2)
N2—C8	1.2841 (18)	C13—C14	1.385 (2)
C1—C6	1.3977 (18)	C13—H13A	0.9500
C1—C2	1.3994 (18)	C14—H14A	0.9500
C1—C7	1.4894 (18)	C15—C16	1.504 (2)
C2—C3	1.3872 (19)	C15—H15A	0.9900
C2—H2A	0.9500	C15—H15B	0.9900
C3—C4	1.3906 (19)	C16—H16A	0.9800
C3—H3A	0.9500	C16—H16B	0.9800
C4—C5	1.3920 (19)	C16—H16C	0.9800
C5—C6	1.3890 (19)	O1W—H3	0.8092
C5—H5A	0.9500	O1W—H4	0.8829
C6—H6A	0.9500	O2W—H5	0.8715
C8—C9	1.4575 (18)	O2W—H6	0.8889

C4—O2—H1	109.6	C10—C9—C8	123.66 (13)
C12—O3—C15	118.06 (11)	C14—C9—C8	117.71 (12)
C7—N1—N2	118.98 (11)	C11—C10—C9	120.55 (13)
C7—N1—H2	123.0	C11—C10—H10A	119.7
N2—N1—H2	117.9	C9—C10—H10A	119.7
C8—N2—N1	114.02 (12)	C10—C11—C12	120.03 (13)
C6—C1—C2	118.69 (12)	C10—C11—H11A	120.0
C6—C1—C7	123.50 (12)	C12—C11—H11A	120.0
C2—C1—C7	117.77 (11)	O3—C12—C13	115.67 (12)
C3—C2—C1	121.23 (12)	O3—C12—C11	124.31 (13)
C3—C2—H2A	119.4	C13—C12—C11	120.02 (13)
C1—C2—H2A	119.4	C14—C13—C12	119.73 (13)
C2—C3—C4	119.37 (12)	C14—C13—H13A	120.1
C2—C3—H3A	120.3	C12—C13—H13A	120.1
C4—C3—H3A	120.3	C13—C14—C9	121.04 (13)
O2—C4—C3	122.42 (12)	C13—C14—H14A	119.5
O2—C4—C5	117.41 (12)	C9—C14—H14A	119.5
C3—C4—C5	120.16 (12)	O3—C15—C16	107.82 (12)
C6—C5—C4	120.21 (12)	O3—C15—H15A	110.1
C6—C5—H5A	119.9	C16—C15—H15A	110.1
C4—C5—H5A	119.9	O3—C15—H15B	110.1
C5—C6—C1	120.31 (12)	C16—C15—H15B	110.1
C5—C6—H6A	119.8	H15A—C15—H15B	108.5
C1—C6—H6A	119.8	C15—C16—H16A	109.5
O1—C7—N1	120.81 (12)	C15—C16—H16B	109.5
O1—C7—C1	121.40 (12)	H16A—C16—H16B	109.5
N1—C7—C1	117.78 (11)	C15—C16—H16C	109.5
N2—C8—C9	122.96 (13)	H16A—C16—H16C	109.5
N2—C8—H8A	118.5	H16B—C16—H16C	109.5
C9—C8—H8A	118.5	H3—O1W—H4	106.9
C10—C9—C14	118.62 (12)	H5—O2W—H6	109.2

C7—N1—N2—C8	−176.66 (11)	N1—N2—C8—C9	−179.90 (11)
C6—C1—C2—C3	0.32 (18)	N2—C8—C9—C10	−6.5 (2)
C7—C1—C2—C3	−177.23 (11)	N2—C8—C9—C14	174.70 (12)
C1—C2—C3—C4	0.81 (19)	C14—C9—C10—C11	0.4 (2)
C2—C3—C4—O2	178.72 (11)	C8—C9—C10—C11	−178.38 (12)
C2—C3—C4—C5	−1.92 (19)	C9—C10—C11—C12	−0.6 (2)
O2—C4—C5—C6	−178.70 (11)	C15—O3—C12—C13	−178.41 (11)
C3—C4—C5—C6	1.91 (19)	C15—O3—C12—C11	1.97 (18)
C4—C5—C6—C1	−0.77 (19)	C10—C11—C12—O3	179.87 (12)
C2—C1—C6—C5	−0.34 (18)	C10—C11—C12—C13	0.3 (2)
C7—C1—C6—C5	177.06 (11)	O3—C12—C13—C14	−179.40 (12)
N2—N1—C7—O1	1.17 (17)	C11—C12—C13—C14	0.2 (2)
N2—N1—C7—C1	−177.57 (10)	C12—C13—C14—C9	−0.4 (2)
C6—C1—C7—O1	−173.58 (12)	C10—C9—C14—C13	0.1 (2)
C2—C1—C7—O1	3.85 (17)	C8—C9—C14—C13	178.96 (12)
C6—C1—C7—N1	5.15 (17)	C12—O3—C15—C16	−176.58 (11)
C2—C1—C7—N1	−177.43 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1ⁱ	0.84	1.77	2.6106 (15)	174
N1—H2···O1Wⁱⁱ	0.85	2.10	2.9278 (16)	167
O1W—H3···O2ⁱⁱⁱ	0.81	2.06	2.8683 (15)	177
O1W—H4···O2W	0.88	1.84	2.7159 (19)	169
O2W—H5···O1^iv	0.87	2.14	2.8558 (18)	139
O2W—H5···N2^iv	0.87	2.55	3.3363 (19)	151
O2W—H6···O3^v	0.89	2.11	2.9791 (17)	165
C6—H6A···O1Wⁱⁱ	0.95	2.36	3.2942 (18)	169
C8—H8A···O1Wⁱⁱ	0.95	2.49	3.3222 (18)	146

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x−1, −y+3/2, z−1/2; (v) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃·2H₂O
M_r	320.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.1655 (1), 17.3895 (3), 13.6202 (2)
β (°)	110.875 (1)
V (Å³)	1585.74 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.29 × 0.16 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.971, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	22228, 5737, 4310
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.155, 1.03
No. of reflections	5737
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1ⁱ	0.84	1.77	2.6106 (15)	174
N1—H2···O1Wⁱⁱ	0.85	2.10	2.9278 (16)	167
O1W—H3···O2ⁱⁱⁱ	0.81	2.06	2.8683 (15)	177
O1W—H4···O2W	0.88	1.84	2.7159 (19)	169
O2W—H5···O1^iv	0.87	2.14	2.8558 (18)	139
O2W—H5···N2^iv	0.87	2.55	3.3363 (19)	151
O2W—H6···O3^v	0.89	2.11	2.9791 (17)	165
C6—H6A···O1Wⁱⁱ	0.95	2.36	3.2942 (18)	169
C8—H8A···O1Wⁱⁱ	0.95	2.49	3.3222 (18)	146

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x−1, −y+3/2, z−1/2; (v) −x+1, −y+2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009. Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

JH thanks the Graduate School, Prince of Songkla University, for partial financial support. The authors thank Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644–o2645. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Horkaew, J., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2012). Acta Cryst. E68, o1069–o1070. CSD CrossRef IUCr Journals Google Scholar
Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o2985. Web of Science CSD CrossRef IUCr Journals Google Scholar
Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067–1071. Web of Science CrossRef PubMed CAS Google Scholar
Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211–219. CAS Google Scholar
Promdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425–429. PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar