(E)-4-Hy­droxy-N′-(4-hy­droxy-3-meth­oxy­benzyl­idene)benzohydrazide

Shalash, M.; Salhin, A.; Adnan, R.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810045162

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3126-o3127

https://doi.org/10.1107/S1600536810045162

Open

access

(E)-4-Hydroxy-N′-(4-hydroxy-3-methoxybenzylidene)benzohydrazide

Marwan Shalash,^a Abdussalam Salhin,^a ‡ Rohana Adnan,^a Chin Sing Yeap ^b § and Hoong-Kun Fun ^b ^*¶

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 2 November 2010; accepted 4 November 2010; online 13 November 2010)

In the title compound, C₁₅H₁₄N₂O₄, the N=C double bond has an E configuration. The two benzene rings make a dihedral angle of 28.59 (6)°. In the crystal, molecules are linked into a three-dimensional network by intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds and stabilized by weak C—H⋯π interactions.

Related literature

For the pharmacological activity of Schiff bases derivatives, see: Zia-ur-Rehman et al. (2009 ); Parashar et al. (1988 ); Hadjoudis et al. (1987 ). For the biological activity of hydrazide derivatives, see: Waisser et al. (1990 ); Hall et al. (1993 ); Salhin et al. (2007 , 2009 ); Tameem et al. (2006 , 2007 , 2008 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Orthorhombic, P n a 2₁
a = 10.9034 (3) Å
b = 8.5533 (2) Å
c = 14.7437 (4) Å
V = 1375.00 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.43 × 0.34 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.958, T_max = 0.984
8269 measured reflections
2098 independent reflections
2033 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.087
S = 1.03
2098 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3ⁱ	0.84 (2)	2.18 (2)	2.9534 (16)	153.0 (17)
N1—H1N1⋯O4ⁱ	0.84 (2)	2.53 (2)	3.2252 (16)	140.0 (17)
O1—H1O1⋯O2ⁱⁱ	0.81 (3)	1.84 (3)	2.6361 (15)	165 (2)
O4—H1O4⋯O1ⁱⁱⁱ	0.87 (2)	1.89 (2)	2.7457 (16)	170 (3)
C2—H2A⋯O2ⁱⁱ	0.93	2.45	3.1271 (17)	129
C15—H15B⋯Cg1^iv	0.96	2.81	3.5620 (14)	132
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z]$ .

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: https://doi.org/10.1107/S1600536810045162/fj2361sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045162/fj2361Isup2.hkl

checkCIF report

Comment top

Syntheses based on Schiff bases have become a major attraction in Chemistry because these products are well known for their pharmacological properties such as anti-tumor, anti-bacterial, anti-oxidant (Zia-ur-Rehman et al., 2009; Parashar et al., 1988) and photochromic activities (Hadjoudis et al., 1987). Many hydrazide derivatives known to have significant biological activities such as monoamine oxidase inhibitory activity, antifungal and tuberculostatic activity (Waisser et al., 1990; Hall et al., 1993). Continuing our interest on the synthesis and application of hydrazone and hydrazide derivatives (Salhin et al., 2007, 2009; Tameem et al., 2006, 2007, 2008), compound (I) (Fig. 1) was hereby synthesized based on Schiff bases by the condensation reaction of 4-hydroxybenzhydrazide and 4-hydroxy-3-methoxybenzaldehyde. The crystal structure is presented here.

The N═C double bond of (I) exist in an E-configuration. The two benzene rings make dihedral angle of 28.59 (6)°. The methoxy group is almost planar with its attached benzene ring [torsion angle 6.3 (2)°]. In the crystal packing, the molecules are linked into a three-dimensional network by intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds and stabilized by weak C—H···π interactions (Fig. 2, Table 1).

Related literature top

For the pharmacological activity of Schiff bases derivatives, see: Zia-ur-Rehman et al. (2009); Parashar et al. (1988); Hadjoudis et al. (1987). For the biological activity of hydrazide derivatives, see: Waisser et al. (1990); Hall et al. (1993); Salhin et al. (2007, 2009); Tameem et al. (2006, 2007, 2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 4-hydroxybenzhydrazide (0.2 g, 1.31 mmol) and 4-hydroxy-3-methoxybenzaldehyde (0.2 g, 1.31 mmol) in 30 ml of methanol containing few drops of acetic acid was refluxed for about 5 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from ethanol. Yellow crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of solution.

Structure description top

For the pharmacological activity of Schiff bases derivatives, see: Zia-ur-Rehman et al. (2009); Parashar et al. (1988); Hadjoudis et al. (1987). For the biological activity of hydrazide derivatives, see: Waisser et al. (1990); Hall et al. (1993); Salhin et al. (2007, 2009); Tameem et al. (2006, 2007, 2008). 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 title compound with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of title compound viewed down b axis, showing the molecules are linked into a three-dimensional network.

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

Crystal data top

C₁₅H₁₄N₂O₄	F(000) = 600
M_r = 286.28	D_x = 1.383 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5243 reflections
a = 10.9034 (3) Å	θ = 2.8–30.1°
b = 8.5533 (2) Å	µ = 0.10 mm⁻¹
c = 14.7437 (4) Å	T = 100 K
V = 1375.00 (6) Å³	Plate, yellow
Z = 4	0.43 × 0.34 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2098 independent reflections
Radiation source: fine-focus sealed tube	2033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 30.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→15
T_min = 0.958, T_max = 0.984	k = −12→8
8269 measured reflections	l = −18→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0687P)² + 0.0626P] where P = (F_o² + 2F_c²)/3
2098 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.35 e Å⁻³
1 restraint	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄	V = 1375.00 (6) Å³
M_r = 286.28	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 10.9034 (3) Å	µ = 0.10 mm⁻¹
b = 8.5533 (2) Å	T = 100 K
c = 14.7437 (4) Å	0.43 × 0.34 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2098 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2033 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.984	R_int = 0.021
8269 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
2098 reflections	Δρ_min = −0.33 e Å⁻³
203 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 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
O1	0.50848 (11)	−0.29559 (13)	−0.39327 (7)	0.0176 (2)
O2	0.47208 (11)	0.16057 (13)	−0.05335 (7)	0.0185 (2)
O3	0.72455 (10)	0.71644 (12)	0.21457 (7)	0.0135 (2)
O4	0.84067 (11)	0.96468 (12)	0.16052 (7)	0.0172 (2)
N1	0.59306 (12)	0.30690 (14)	−0.14694 (8)	0.0134 (2)
N2	0.61084 (12)	0.41786 (14)	−0.07972 (8)	0.0130 (2)
C1	0.51462 (13)	0.09777 (17)	−0.29247 (9)	0.0122 (3)
H1A	0.5163	0.2022	−0.3099	0.015*
C2	0.51039 (13)	−0.01823 (17)	−0.35842 (9)	0.0131 (3)
H2A	0.5080	0.0083	−0.4196	0.016*
C3	0.50984 (13)	−0.17538 (18)	−0.33189 (10)	0.0133 (3)
C4	0.51091 (14)	−0.21469 (17)	−0.23966 (9)	0.0149 (3)
H4A	0.5106	−0.3191	−0.2221	0.018*
C5	0.51242 (13)	−0.09687 (17)	−0.17432 (9)	0.0138 (3)
H5A	0.5107	−0.1230	−0.1131	0.017*
C6	0.51643 (13)	0.05963 (16)	−0.20017 (9)	0.0115 (3)
C7	0.52375 (13)	0.17934 (17)	−0.12730 (9)	0.0127 (3)
C8	0.68511 (14)	0.52860 (17)	−0.10081 (9)	0.0133 (3)
H8A	0.7178	0.5333	−0.1590	0.016*
C9	0.71871 (13)	0.64765 (17)	−0.03369 (9)	0.0127 (3)
C10	0.78103 (14)	0.78203 (17)	−0.06151 (10)	0.0148 (3)
H10A	0.7962	0.7984	−0.1228	0.018*
C11	0.82067 (14)	0.89195 (17)	0.00196 (10)	0.0153 (3)
H11A	0.8615	0.9815	−0.0172	0.018*
C12	0.79915 (14)	0.86768 (16)	0.09385 (9)	0.0130 (3)
C13	0.73610 (12)	0.73180 (16)	0.12227 (9)	0.0114 (3)
C14	0.69530 (14)	0.62378 (17)	0.05952 (10)	0.0127 (3)
H14A	0.6526	0.5356	0.0786	0.015*
C15	0.67731 (14)	0.57037 (17)	0.24666 (10)	0.0159 (3)
H15A	0.6747	0.5713	0.3117	0.024*
H15B	0.7295	0.4869	0.2265	0.024*
H15C	0.5961	0.5549	0.2232	0.024*
H1N1	0.638 (2)	0.311 (2)	−0.1935 (17)	0.018 (5)*
H1O1	0.501 (2)	−0.252 (3)	−0.442 (2)	0.043 (8)*
H1O4	0.890 (2)	1.034 (3)	0.138 (2)	0.033 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0328 (6)	0.0102 (5)	0.0099 (4)	0.0016 (4)	−0.0035 (4)	−0.0002 (4)
O2	0.0279 (6)	0.0167 (5)	0.0109 (4)	−0.0050 (4)	0.0046 (4)	−0.0017 (4)
O3	0.0187 (5)	0.0131 (5)	0.0088 (4)	−0.0029 (4)	0.0002 (4)	0.0007 (3)
O4	0.0272 (6)	0.0118 (5)	0.0125 (4)	−0.0068 (4)	−0.0022 (4)	−0.0013 (4)
N1	0.0181 (5)	0.0127 (5)	0.0093 (5)	−0.0021 (4)	0.0027 (4)	−0.0035 (4)
N2	0.0181 (6)	0.0111 (5)	0.0099 (5)	−0.0010 (4)	−0.0003 (4)	−0.0031 (4)
C1	0.0153 (6)	0.0109 (6)	0.0104 (5)	−0.0005 (5)	−0.0001 (5)	0.0011 (5)
C2	0.0182 (7)	0.0101 (6)	0.0109 (6)	−0.0001 (5)	−0.0016 (5)	0.0000 (4)
C3	0.0178 (6)	0.0114 (6)	0.0109 (6)	0.0002 (5)	−0.0012 (5)	−0.0009 (5)
C4	0.0228 (7)	0.0106 (6)	0.0111 (6)	−0.0009 (5)	−0.0013 (5)	0.0014 (5)
C5	0.0190 (7)	0.0127 (7)	0.0096 (5)	−0.0011 (5)	−0.0010 (5)	0.0005 (5)
C6	0.0142 (6)	0.0109 (6)	0.0095 (5)	−0.0012 (5)	0.0001 (5)	−0.0019 (5)
C7	0.0159 (6)	0.0120 (6)	0.0104 (6)	0.0003 (5)	−0.0003 (5)	−0.0014 (5)
C8	0.0165 (7)	0.0137 (6)	0.0099 (5)	0.0002 (5)	0.0003 (5)	−0.0017 (4)
C9	0.0152 (6)	0.0127 (6)	0.0101 (5)	−0.0003 (5)	−0.0007 (4)	−0.0015 (4)
C10	0.0192 (7)	0.0141 (6)	0.0112 (5)	−0.0019 (5)	0.0010 (5)	−0.0003 (5)
C11	0.0212 (7)	0.0122 (6)	0.0125 (6)	−0.0026 (5)	0.0003 (5)	0.0006 (5)
C12	0.0174 (6)	0.0104 (6)	0.0111 (5)	−0.0001 (5)	−0.0008 (5)	−0.0008 (5)
C13	0.0135 (6)	0.0110 (6)	0.0099 (6)	0.0003 (5)	−0.0003 (5)	0.0008 (4)
C14	0.0142 (6)	0.0117 (6)	0.0122 (5)	−0.0015 (5)	0.0000 (5)	0.0004 (5)
C15	0.0211 (7)	0.0145 (6)	0.0119 (6)	−0.0026 (5)	0.0010 (5)	0.0030 (5)

Geometric parameters (Å, º) top

O1—C3	1.3698 (17)	C4—H4A	0.9300
O1—H1O1	0.82 (3)	C5—C6	1.393 (2)
O2—C7	1.2377 (18)	C5—H5A	0.9300
O3—C13	1.3729 (16)	C6—C7	1.4862 (18)
O3—C15	1.4318 (17)	C8—C9	1.4664 (18)
O4—C12	1.3637 (17)	C8—H8A	0.9300
O4—H1O4	0.86 (3)	C9—C10	1.397 (2)
N1—C7	1.3584 (19)	C9—C14	1.4127 (18)
N1—N2	1.3859 (15)	C10—C11	1.395 (2)
N1—H1N1	0.84 (2)	C10—H10A	0.9300
N2—C8	1.2844 (19)	C11—C12	1.3905 (19)
C1—C2	1.3900 (19)	C11—H11A	0.9300
C1—C6	1.3995 (19)	C12—C13	1.4139 (19)
C1—H1A	0.9300	C13—C14	1.3811 (19)
C2—C3	1.400 (2)	C14—H14A	0.9300
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.4008 (19)	C15—H15B	0.9600
C4—C5	1.3943 (19)	C15—H15C	0.9600

C3—O1—H1O1	104 (2)	N2—C8—C9	120.42 (12)
C13—O3—C15	116.36 (11)	N2—C8—H8A	119.8
C12—O4—H1O4	110.3 (18)	C9—C8—H8A	119.8
C7—N1—N2	118.39 (11)	C10—C9—C14	119.50 (12)
C7—N1—H1N1	122.1 (14)	C10—C9—C8	119.66 (12)
N2—N1—H1N1	118.1 (14)	C14—C9—C8	120.73 (12)
C8—N2—N1	114.84 (11)	C11—C10—C9	120.55 (13)
C2—C1—C6	120.95 (13)	C11—C10—H10A	119.7
C2—C1—H1A	119.5	C9—C10—H10A	119.7
C6—C1—H1A	119.5	C12—C11—C10	120.04 (14)
C1—C2—C3	119.35 (13)	C12—C11—H11A	120.0
C1—C2—H2A	120.3	C10—C11—H11A	120.0
C3—C2—H2A	120.3	O4—C12—C11	123.74 (13)
O1—C3—C2	122.42 (13)	O4—C12—C13	116.61 (12)
O1—C3—C4	117.47 (13)	C11—C12—C13	119.57 (13)
C2—C3—C4	120.11 (13)	O3—C13—C14	124.78 (12)
C5—C4—C3	119.82 (14)	O3—C13—C12	114.65 (12)
C5—C4—H4A	120.1	C14—C13—C12	120.53 (12)
C3—C4—H4A	120.1	C13—C14—C9	119.79 (13)
C6—C5—C4	120.40 (13)	C13—C14—H14A	120.1
C6—C5—H5A	119.8	C9—C14—H14A	120.1
C4—C5—H5A	119.8	O3—C15—H15A	109.5
C5—C6—C1	119.33 (13)	O3—C15—H15B	109.5
C5—C6—C7	117.78 (12)	H15A—C15—H15B	109.5
C1—C6—C7	122.89 (13)	O3—C15—H15C	109.5
O2—C7—N1	123.04 (13)	H15A—C15—H15C	109.5
O2—C7—C6	121.53 (13)	H15B—C15—H15C	109.5
N1—C7—C6	115.41 (12)

C7—N1—N2—C8	174.70 (13)	N2—C8—C9—C10	−168.42 (14)
C6—C1—C2—C3	−1.0 (2)	N2—C8—C9—C14	15.4 (2)
C1—C2—C3—O1	−178.53 (13)	C14—C9—C10—C11	0.3 (2)
C1—C2—C3—C4	1.3 (2)	C8—C9—C10—C11	−175.92 (14)
O1—C3—C4—C5	179.95 (13)	C9—C10—C11—C12	0.5 (2)
C2—C3—C4—C5	0.1 (2)	C10—C11—C12—O4	176.23 (14)
C3—C4—C5—C6	−1.9 (2)	C10—C11—C12—C13	−0.5 (2)
C4—C5—C6—C1	2.2 (2)	C15—O3—C13—C14	6.3 (2)
C4—C5—C6—C7	−177.19 (13)	C15—O3—C13—C12	−171.28 (12)
C2—C1—C6—C5	−0.8 (2)	O4—C12—C13—O3	0.37 (18)
C2—C1—C6—C7	178.59 (13)	C11—C12—C13—O3	177.34 (14)
N2—N1—C7—O2	2.8 (2)	O4—C12—C13—C14	−177.32 (13)
N2—N1—C7—C6	−175.54 (12)	C11—C12—C13—C14	−0.3 (2)
C5—C6—C7—O2	−34.2 (2)	O3—C13—C14—C9	−176.25 (13)
C1—C6—C7—O2	146.44 (15)	C12—C13—C14—C9	1.2 (2)
C5—C6—C7—N1	144.17 (13)	C10—C9—C14—C13	−1.2 (2)
C1—C6—C7—N1	−35.2 (2)	C8—C9—C14—C13	175.02 (13)
N1—N2—C8—C9	−175.73 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.84 (2)	2.18 (2)	2.9534 (16)	153.0 (17)
N1—H1N1···O4ⁱ	0.84 (2)	2.53 (2)	3.2252 (16)	140.0 (17)
O1—H1O1···O2ⁱⁱ	0.81 (3)	1.84 (3)	2.6361 (15)	165 (2)
O4—H1O4···O1ⁱⁱⁱ	0.87 (2)	1.89 (2)	2.7457 (16)	170 (3)
C2—H2A···O2ⁱⁱ	0.93	2.45	3.1271 (17)	129
C15—H15B···Cg1^iv	0.96	2.81	3.5620 (14)	132

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄
M_r	286.28
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	10.9034 (3), 8.5533 (2), 14.7437 (4)
V (Å³)	1375.00 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.43 × 0.34 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.958, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8269, 2098, 2033
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.087, 1.03
No. of reflections	2098
No. of parameters	203
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.33

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.84 (2)	2.18 (2)	2.9534 (16)	153.0 (17)
N1—H1N1···O4ⁱ	0.84 (2)	2.53 (2)	3.2252 (16)	140.0 (17)
O1—H1O1···O2ⁱⁱ	0.81 (3)	1.84 (3)	2.6361 (15)	165 (2)
O4—H1O4···O1ⁱⁱⁱ	0.87 (2)	1.89 (2)	2.7457 (16)	170 (3)
C2—H2A···O2ⁱⁱ	0.9300	2.4500	3.1271 (17)	129.00
C15—H15B···Cg1^iv	0.9600	2.8100	3.5620 (14)	132.00

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

Footnotes

‡Additional correspondence author, e-mail: abdussalam@usm.my.

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

MS, AS and RA acknowledge financial support by the Universiti Sains Malaysia (USM) under Science Fund Grant No. 1001/PKIMIA/811055. HKF and CSY thank USM for the Research University Grant No. 1001/PFIZIK/811160.

References

Bruker (2009). 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
Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, J. (1987). Tetrahedron, 43, 1345–1360. CrossRef CAS Web of Science Google Scholar
Hall, L. H., Mohney, B. K. & Kier, L. B. (1993). Quant. Struct. Act. Relat. 12, 44–48. CrossRef CAS Web of Science Google Scholar
Parashar, R. K., Sharma, R. C., Kumar, A. & Mohan, G. (1988). Inorg. Chim. Acta, 151, 201–208. CrossRef CAS Web of Science Google Scholar
Salhin, A., Abdul Razak, N. & Rahman, I. A. (2009). Acta Cryst. E65, o1221–o1222. Web of Science CSD CrossRef IUCr Journals Google Scholar
Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880. Web of Science CSD CrossRef IUCr Journals 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
Tameem, A. A., Saad, B., Salhin, A. M., Jebas, S. R. & Fun, H.-K. (2008). Acta Cryst. E64, o679–o680. Web of Science CrossRef IUCr Journals Google Scholar
Tameem, A. A., Salhin, A., Saad, B., Rahman, I. A., Saleh, M. I., Ng, S.-L. & Fun, H.-K. (2006). Acta Cryst. E62, o5686–o5688. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tameem, A. A., Salhin, A., Saad, B., Rahman, I. A., Saleh, M. I., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o57–o58. Web of Science CSD CrossRef IUCr Journals Google Scholar
Waisser, K., Houngbedji, N., Odlerova, Z., Thiel, W. & Mayer, R. (1990). Pharmazie, 45, 141–142. CAS PubMed Web of Science Google Scholar
Zia-ur-Rehman, M., Choudary, J. A., Elsegood, M. R. J., Siddiqui, H. L. & Khan, K. M. (2009). Eur. J. Med. Chem. 44, 1311–1316. Web of Science PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3126-o3127

https://doi.org/10.1107/S1600536810045162

Open

access