(E)-4-Bromo-N′-(4-hy­droxy-3-meth­oxy­benzyl­idene)benzohydrazide monohydrate

Horkaew, J.; Chantrapromma, S.; Anantapong, T.; Kanjana-Opas, A.; Fun, H.-K.

doi:10.1107/S160053681201032X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1069-o1070

doi:10.1107/S160053681201032X

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(E)-4-Bromo-N′-(4-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate

Jirapa Horkaew,^a Suchada Chantrapromma,^b ^*‡ Teerasak Anantapong,^c Akkharawit Kanjana-Opas ^c and Hoong-Kun Fun ^d §

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cDepartment of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 15 February 2012; accepted 8 March 2012; online 14 March 2012)

In the title compound, C₁₅H₁₃BrN₂O₃·H₂O, the dihedral angle between the two benzene rings is 13.92 (6)°. The methoxy group of the 4-hydroxy-3-methoxyphenyl is almost coplanar with its bound benzene ring, as seen by the C_methyl—O—C—C torsion angle of −0.35 (16)°. In the crystal, molecules are linked into a three-dimensional network by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds and also weak C—H⋯O interactions. A short C⋯O contact of 3.0191 (15) Å is also present.

Related literature

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

Experimental

Crystal data

C₁₅H₁₃BrN₂O₃·H₂O
M_r = 367.19
Monoclinic, P 2₁ /c
a = 7.9772 (7) Å
b = 21.446 (2) Å
c = 10.3928 (7) Å
β = 119.479 (5)°
V = 1547.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.68 mm⁻¹
T = 100 K
0.58 × 0.21 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.306, T_max = 0.756
18815 measured reflections
5602 independent reflections
4894 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.065
S = 1.04
5602 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O1Wⁱ	0.80	1.79	2.5867 (14)	170
N1—H1N1⋯O3ⁱⁱ	0.86	2.18	3.0107 (16)	162
O1W—H1OW⋯O1ⁱⁱⁱ	0.82	1.93	2.7409 (14)	171
O1W—H2OW⋯O1^iv	0.78	2.16	2.8883 (14)	154
O1W—H2OW⋯N2^iv	0.78	2.49	3.0971 (16)	136
C6—H6A⋯O3ⁱⁱ	0.95	2.59	3.4832 (15)	156
C8—H8A⋯O3ⁱⁱ	0.95	2.40	3.2604 (17)	150
C10—H10A⋯O1W^v	0.95	2.45	3.3933 (15)	172
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+1; (iv) x+1, y, z; (v) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S160053681201032X/fj2521sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201032X/fj2521Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201032X/fj2521Isup3.cml

checkCIF report

Comment top

As part of our study on bioactivity of hydrazone and benzohydrazide derivatives, the title compound is one of the several benzohydrazide derivatives which were synthesized and tested for biological activity. It have been known that some benzohydrazides possess various biological properties, such as antibacterial and antifungal (Loncle et al., 2004), and antiproliferative (Raj et al., 2007) activities. We have previously reported some crystal structures of this category of compounds (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). The title compound (I) was synthesized in order to study the effect of functional groups and their positions on their bioactivities by comparing with the closely related structures in our research project. (I) was screened for antibacterial and antioxidant activities. Our biological testing found that (I) exhibits potent antioxidant activity whereas inactive against the tested bacteria strains which are Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecalis, Pseudomonas aeruginosa, Salmonella typhi and Shigella sonnei. Herein we report the crystal structure of (I).

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₅H₁₃BrN₂O₃.H₂O, comprises of a molecule of benzohydrazide and one water solvent molecule. The molecule of benzohydrazide exists in a trans-configuration with respect to the C8═N2 bond [1.2853 (14) Å] and the torsion angle N1–N2–C8–C9 = 178.54 (10)°. The molecule is twisted with the dihedral angle between the two phenyl rings being 13.92 (6)°. The methoxy group of the 4-hydroxy-3-methoxyphenyl is co-planar with its bound benzene ring [C15–O2–C11–C10 = 0.35 (16)°].

The middle bridge fragment (O1/C7/N1/N2/C8) is essentially planar with the torsion angle N2–N1–C7–O1 = -0.21 (17)°. The mean plane through this bridge makes the dihedral angles of 12.71 (7) and 1.25 (7)° with the 4-bromophenyl and 4 benzene rings, respectively. The methoxy group of 4-hydroxy-3-methoxyphenyl is co-planar with its bound benzene ring with the torsion angle C15–O2–C11–C10 = 0.35 (16)° and the r.m.s 0.0063 (2) Å for the eight non H atoms. Bond distances are in normal ranges (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O, O—H···N and O—H···O hydrogen bonds together with weak C—H···O interactions (Table 1) into a three dimensional network. A C8···O2ⁱ[3.0191 (15) Å] short contact was presented.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2011); Horkaew et al. (2011); Promdet et al. (2011). For background and applications of benzohydrazide derivatives, see: Loncle et al. (2004); 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-bromobenzohydrazide (2 mmol, 0.43 g) in ethanol (15 ml). The solution of 4-hydroxy-3-methoxy-benzaldehyde (2 mmol, 0.30 g) in ethanol (15 ml) was then added slowly to the reaction. The mixture was refluxed for around 5 hr and the white solid of the product that appeared was collected by filtration, washed with ethanol and dried in air. Colorless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature after several days, Mp. 513 K (decomposed).

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 55% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed approximately along the a axis, showing 3D network. Hydrogen bonds were drawn as dashed lines.

(E)-4-Bromo-N'-(4-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₅H₁₃BrN₂O₃·H₂O	F(000) = 744
M_r = 367.19	D_x = 1.576 Mg m⁻³
Monoclinic, P2₁/c	Melting point > 513 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9772 (7) Å	Cell parameters from 5602 reflections
b = 21.446 (2) Å	θ = 2.4–32.6°
c = 10.3928 (7) Å	µ = 2.68 mm⁻¹
β = 119.479 (5)°	T = 100 K
V = 1547.8 (2) Å³	Block, colorless
Z = 4	0.58 × 0.21 × 0.11 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	5602 independent reflections
Radiation source: sealed tube	4894 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 32.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→12
T_min = 0.306, T_max = 0.756	k = −29→32
18815 measured reflections	l = −15→15

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0304P)² + 0.5617P] where P = (F_o² + 2F_c²)/3
5602 reflections	(Δ/σ)_max = 0.009
200 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₃·H₂O	V = 1547.8 (2) Å³
M_r = 367.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9772 (7) Å	µ = 2.68 mm⁻¹
b = 21.446 (2) Å	T = 100 K
c = 10.3928 (7) Å	0.58 × 0.21 × 0.11 mm
β = 119.479 (5)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	5602 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4894 reflections with I > 2σ(I)
T_min = 0.306, T_max = 0.756	R_int = 0.024
18815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.04	Δρ_max = 0.54 e Å⁻³
5602 reflections	Δρ_min = −0.54 e Å⁻³
200 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 100.0 (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
Br1	1.165101 (18)	1.138681 (6)	1.032760 (13)	0.02180 (4)
O1	0.31020 (12)	0.98324 (4)	0.62686 (11)	0.02206 (18)
O2	−0.26566 (11)	0.74388 (4)	0.19684 (10)	0.01696 (15)
O3	−0.14414 (12)	0.64604 (4)	0.11703 (10)	0.01614 (15)
H1O3	−0.1053	0.6238	0.0752	0.024*
N1	0.50431 (13)	0.91557 (4)	0.59638 (11)	0.01464 (16)
H1N1	0.6171	0.9016	0.6218	0.018*
N2	0.34933 (13)	0.87658 (4)	0.51278 (11)	0.01445 (16)
C1	0.64474 (16)	1.00888 (5)	0.74049 (12)	0.01489 (18)
C2	0.62537 (18)	1.05722 (6)	0.82220 (15)	0.0223 (2)
H2A	0.5052	1.0635	0.8185	0.027*
C3	0.77907 (19)	1.09623 (6)	0.90869 (15)	0.0233 (2)
H3A	0.7652	1.1289	0.9644	0.028*
C4	0.95314 (17)	1.08667 (5)	0.91237 (13)	0.0176 (2)
C5	0.97598 (17)	1.03960 (6)	0.83136 (13)	0.0186 (2)
H5A	1.0960	1.0339	0.8344	0.022*
C6	0.82108 (17)	1.00077 (5)	0.74535 (13)	0.0178 (2)
H6A	0.8356	0.9684	0.6893	0.021*
C7	0.47302 (16)	0.96867 (5)	0.65048 (12)	0.01518 (19)
C8	0.39443 (15)	0.82791 (5)	0.46425 (12)	0.01448 (18)
H8A	0.5240	0.8228	0.4859	0.017*
C9	0.25378 (15)	0.78044 (5)	0.37726 (12)	0.01375 (18)
C10	0.05771 (15)	0.78701 (5)	0.33432 (12)	0.01418 (18)
H10A	0.0146	0.8225	0.3646	0.017*
C11	−0.07205 (15)	0.74162 (5)	0.24783 (12)	0.01331 (18)
C12	−0.00870 (15)	0.68869 (5)	0.20363 (12)	0.01369 (18)
C13	0.18522 (16)	0.68186 (5)	0.24792 (13)	0.01568 (19)
H13A	0.2288	0.6460	0.2194	0.019*
C14	0.31573 (16)	0.72779 (5)	0.33436 (13)	0.01619 (19)
H14A	0.4484	0.7231	0.3643	0.019*
C15	−0.33607 (17)	0.79716 (6)	0.23765 (15)	0.0201 (2)
H15A	−0.4763	0.7943	0.1930	0.030*
H15B	−0.3026	0.8350	0.2024	0.030*
H15C	−0.2776	0.7988	0.3455	0.030*
O1W	0.94692 (12)	0.92018 (4)	0.45250 (10)	0.01886 (16)
H1OW	0.8746	0.9503	0.4230	0.028*
H2OW	1.0559	0.9287	0.4881	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02481 (7)	0.01815 (6)	0.01611 (6)	−0.00733 (4)	0.00520 (5)	−0.00200 (4)
O1	0.0137 (4)	0.0200 (4)	0.0292 (5)	0.0032 (3)	0.0080 (3)	−0.0033 (3)
O2	0.0091 (3)	0.0177 (4)	0.0223 (4)	−0.0001 (3)	0.0064 (3)	−0.0044 (3)
O3	0.0129 (3)	0.0161 (4)	0.0196 (4)	−0.0031 (3)	0.0081 (3)	−0.0051 (3)
N1	0.0099 (4)	0.0142 (4)	0.0170 (4)	−0.0005 (3)	0.0045 (3)	−0.0019 (3)
N2	0.0109 (4)	0.0147 (4)	0.0146 (4)	−0.0018 (3)	0.0039 (3)	−0.0008 (3)
C1	0.0152 (5)	0.0122 (4)	0.0150 (4)	0.0006 (3)	0.0056 (4)	0.0007 (3)
C2	0.0182 (5)	0.0206 (5)	0.0256 (6)	0.0023 (4)	0.0088 (5)	−0.0057 (4)
C3	0.0222 (6)	0.0194 (5)	0.0238 (6)	0.0011 (4)	0.0080 (5)	−0.0064 (4)
C4	0.0199 (5)	0.0145 (5)	0.0138 (5)	−0.0031 (4)	0.0046 (4)	−0.0002 (4)
C5	0.0184 (5)	0.0189 (5)	0.0194 (5)	−0.0048 (4)	0.0100 (4)	−0.0032 (4)
C6	0.0186 (5)	0.0166 (5)	0.0192 (5)	−0.0034 (4)	0.0101 (4)	−0.0039 (4)
C7	0.0137 (4)	0.0141 (4)	0.0154 (5)	0.0013 (3)	0.0053 (4)	0.0007 (4)
C8	0.0106 (4)	0.0154 (4)	0.0152 (5)	0.0000 (3)	0.0046 (4)	0.0007 (4)
C9	0.0112 (4)	0.0141 (4)	0.0145 (4)	−0.0005 (3)	0.0052 (4)	−0.0001 (3)
C10	0.0121 (4)	0.0143 (4)	0.0150 (5)	0.0001 (3)	0.0058 (4)	−0.0007 (4)
C11	0.0100 (4)	0.0147 (4)	0.0145 (4)	0.0003 (3)	0.0054 (4)	0.0006 (3)
C12	0.0116 (4)	0.0141 (4)	0.0142 (4)	−0.0015 (3)	0.0055 (4)	−0.0009 (3)
C13	0.0131 (4)	0.0148 (4)	0.0192 (5)	0.0006 (4)	0.0080 (4)	−0.0020 (4)
C14	0.0109 (4)	0.0172 (5)	0.0198 (5)	−0.0002 (4)	0.0070 (4)	−0.0013 (4)
C15	0.0134 (5)	0.0214 (5)	0.0261 (6)	0.0014 (4)	0.0103 (4)	−0.0048 (4)
O1W	0.0147 (4)	0.0161 (4)	0.0266 (4)	0.0023 (3)	0.0108 (3)	0.0042 (3)

Geometric parameters (Å, º) top

Br1—C4	1.8939 (12)	C5—H5A	0.9500
O1—C7	1.2374 (14)	C6—H6A	0.9500
O2—C11	1.3650 (13)	C8—C9	1.4541 (15)
O2—C15	1.4266 (14)	C8—H8A	0.9500
O3—C12	1.3627 (13)	C9—C14	1.3911 (15)
O3—H1O3	0.8032	C9—C10	1.4066 (15)
N1—C7	1.3467 (14)	C10—C11	1.3825 (15)
N1—N2	1.3876 (13)	C10—H10A	0.9500
N1—H1N1	0.8572	C11—C12	1.4082 (15)
N2—C8	1.2853 (14)	C12—C13	1.3876 (15)
C1—C6	1.3935 (16)	C13—C14	1.3930 (16)
C1—C2	1.3959 (16)	C13—H13A	0.9500
C1—C7	1.4947 (16)	C14—H14A	0.9500
C2—C3	1.3879 (18)	C15—H15A	0.9800
C2—H2A	0.9500	C15—H15B	0.9800
C3—C4	1.3854 (18)	C15—H15C	0.9800
C3—H3A	0.9500	O1W—H1OW	0.8179
C4—C5	1.3828 (16)	O1W—H2OW	0.7806
C5—C6	1.3900 (16)

C11—O2—C15	116.68 (9)	N2—C8—H8A	118.9
C12—O3—H1O3	111.4	C9—C8—H8A	118.9
C7—N1—N2	118.68 (9)	C14—C9—C10	119.65 (10)
C7—N1—H1N1	123.2	C14—C9—C8	118.72 (9)
N2—N1—H1N1	117.4	C10—C9—C8	121.63 (10)
C8—N2—N1	113.57 (9)	C11—C10—C9	119.71 (10)
C6—C1—C2	118.85 (11)	C11—C10—H10A	120.1
C6—C1—C7	123.27 (10)	C9—C10—H10A	120.1
C2—C1—C7	117.87 (10)	O2—C11—C10	124.71 (10)
C3—C2—C1	120.97 (11)	O2—C11—C12	114.91 (9)
C3—C2—H2A	119.5	C10—C11—C12	120.37 (9)
C1—C2—H2A	119.5	O3—C12—C13	122.71 (10)
C4—C3—C2	118.85 (11)	O3—C12—C11	117.47 (9)
C4—C3—H3A	120.6	C13—C12—C11	119.82 (10)
C2—C3—H3A	120.6	C12—C13—C14	119.78 (10)
C5—C4—C3	121.46 (11)	C12—C13—H13A	120.1
C5—C4—Br1	119.34 (9)	C14—C13—H13A	120.1
C3—C4—Br1	119.20 (9)	C9—C14—C13	120.66 (10)
C4—C5—C6	119.15 (11)	C9—C14—H14A	119.7
C4—C5—H5A	120.4	C13—C14—H14A	119.7
C6—C5—H5A	120.4	O2—C15—H15A	109.5
C5—C6—C1	120.70 (11)	O2—C15—H15B	109.5
C5—C6—H6A	119.6	H15A—C15—H15B	109.5
C1—C6—H6A	119.6	O2—C15—H15C	109.5
O1—C7—N1	121.53 (10)	H15A—C15—H15C	109.5
O1—C7—C1	121.85 (10)	H15B—C15—H15C	109.5
N1—C7—C1	116.62 (9)	H1OW—O1W—H2OW	114.1
N2—C8—C9	122.22 (10)

C7—N1—N2—C8	178.70 (10)	N2—C8—C9—C14	−177.20 (11)
C6—C1—C2—C3	−0.88 (19)	N2—C8—C9—C10	3.67 (17)
C7—C1—C2—C3	179.75 (12)	C14—C9—C10—C11	−1.09 (16)
C1—C2—C3—C4	0.3 (2)	C8—C9—C10—C11	178.04 (10)
C2—C3—C4—C5	0.4 (2)	C15—O2—C11—C10	−0.35 (16)
C2—C3—C4—Br1	−178.89 (10)	C15—O2—C11—C12	−179.25 (10)
C3—C4—C5—C6	−0.52 (19)	C9—C10—C11—O2	−178.33 (10)
Br1—C4—C5—C6	178.78 (9)	C9—C10—C11—C12	0.52 (16)
C4—C5—C6—C1	−0.09 (18)	O2—C11—C12—O3	−0.29 (14)
C2—C1—C6—C5	0.77 (18)	C10—C11—C12—O3	−179.25 (10)
C7—C1—C6—C5	−179.89 (11)	O2—C11—C12—C13	179.38 (10)
N2—N1—C7—O1	−0.21 (17)	C10—C11—C12—C13	0.42 (16)
N2—N1—C7—C1	179.66 (9)	O3—C12—C13—C14	178.87 (10)
C6—C1—C7—O1	−166.86 (12)	C11—C12—C13—C14	−0.78 (17)
C2—C1—C7—O1	12.48 (17)	C10—C9—C14—C13	0.74 (17)
C6—C1—C7—N1	13.26 (16)	C8—C9—C14—C13	−178.42 (11)
C2—C1—C7—N1	−167.40 (11)	C12—C13—C14—C9	0.20 (18)
N1—N2—C8—C9	178.54 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1Wⁱ	0.80	1.79	2.5867 (14)	170
N1—H1N1···O3ⁱⁱ	0.86	2.18	3.0107 (16)	162
O1W—H1OW···O1ⁱⁱⁱ	0.82	1.93	2.7409 (14)	171
O1W—H2OW···O1^iv	0.78	2.16	2.8883 (14)	154
O1W—H2OW···N2^iv	0.78	2.49	3.0971 (16)	136
C6—H6A···O3ⁱⁱ	0.95	2.59	3.4832 (15)	156
C8—H8A···O2ⁱⁱ	0.95	2.46	3.0191 (15)	118
C8—H8A···O3ⁱⁱ	0.95	2.40	3.2604 (17)	150
C10—H10A···O1W^v	0.95	2.45	3.3933 (15)	172

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₃·H₂O
M_r	367.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.9772 (7), 21.446 (2), 10.3928 (7)
β (°)	119.479 (5)
V (Å³)	1547.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.68
Crystal size (mm)	0.58 × 0.21 × 0.11

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.306, 0.756
No. of measured, independent and observed [I > 2σ(I)] reflections	18815, 5602, 4894
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.065, 1.04
No. of reflections	5602
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.54

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O3—H1O3···O1Wⁱ	0.80	1.79	2.5867 (14)	170
N1—H1N1···O3ⁱⁱ	0.86	2.18	3.0107 (16)	162
O1W—H1OW···O1ⁱⁱⁱ	0.82	1.93	2.7409 (14)	171
O1W—H2OW···O1^iv	0.78	2.16	2.8883 (14)	154
O1W—H2OW···N2^iv	0.78	2.49	3.0971 (16)	136
C6—H6A···O3ⁱⁱ	0.95	2.59	3.4832 (15)	156
C8—H8A···O3ⁱⁱ	0.95	2.40	3.2604 (17)	150
C10—H10A···O1W^v	0.95	2.45	3.3933 (15)	172

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Thomson Reuters ResearcherID: A-3561-2009. Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

JH thanks the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education, and the Graduate School, Prince of Songkla University, for financial support. The authors thank the Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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