(E)-2-Meth­oxy-N′-(2,4,6-trihy­droxy­benzyl­idene)benzohydrazide

Taha, M.; Baharudin, M.S.; Ismail, N.H.; Shah, S.A.A.; Yousuf, S.

doi:10.1107/S1600536813001748

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o277

doi:10.1107/S1600536813001748

Open

access

(E)-2-Methoxy-N′-(2,4,6-trihydroxybenzylidene)benzohydrazide

Muhammad Taha,^a M. Syukri Baharudin,^a Nor Hadiani Ismail,^b Syed Adnan Ali Shah ^a,^c and Sammer Yousuf ^d ^*

^aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E. Malaysia, ^bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D. E. Malaysia, ^cDepartment of Pharmacology and Chemistry, Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Puncak Alam, Selangor D. E., Malaysia, and ^dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 11 January 2013; accepted 17 January 2013; online 23 January 2013)

In the title hydrazone derivative, C₁₅H₁₄N₂O₅, the benzene rings are twisted by 7.55 (8)° with respect to each other. The azomethine double bond adopts an E conformation. The molecular structure is stabilized by intramolecular O—H⋯N and N—H⋯O hydrogen bonds, generating S6 ring motifs. In the crystal, molecules are linked into a three-dimensional network by O—H⋯O hydrogen bonds.

Related literature

For applications and biological activity of Schiff bases, see: Khan et al. (2011 , 2012 ); Rada & Leto (2008 ); Almasirad et al. (2006 ). For related structures, see: Taha et al. (2012 ); Shen et al. (2012 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₅
M_r = 302.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.4580 (4) Å
b = 13.4772 (8) Å
c = 16.3169 (9) Å
V = 1420.15 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 273 K
0.34 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.964, T_max = 0.978
8414 measured reflections
2643 independent reflections
2481 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.07
2643 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.84 (3)	1.88 (2)	2.6243 (18)	147 (2)
N2—H2A⋯O5	0.851 (19)	1.923 (19)	2.5981 (18)	135.4 (17)
O3—H2B⋯O4ⁱ	0.86 (2)	1.79 (2)	2.6452 (17)	175 (2)
O2—H3A⋯O1ⁱⁱ	0.93 (3)	1.92 (3)	2.8513 (18)	172 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813001748/rz5037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001748/rz5037Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001748/rz5037Isup3.cml

checkCIF report

Comment top

Hydrazone derivatives represent an important class of organic compounds. Due to their biological activities (Khan et al., 2011, 2012; Rada & Leto, 2008; Almasirad et al., 2006) the research for this class of compounds is an area of great interest. The title compound is a hydrazone derivatives synthesized as a part of our ongoing research to establish a library of bioactive hydrazone derivatives.

The structure of the title compound (Fig. 1) is similar to that of the previously published compound N'-(3,4-dihydroxybenzylidene)-2- methoxybenzohydrazide (Shen et al., 2012) with the difference that the 3,4-dihydroxy benzene ring is replaced by a 2,4,6-trihydroxy benzene ring (C1–C6). The dihedral angle between the two benzene rings is 7.55 (8)°. The bond lengths and angles were found to be similar to those observed in structurally related benzohydrazide derivatives (Taha et al., 2012; Shen et al., 2012). Intramolecular O1—H1A···N1 and N2—H2A···O5 hydrogen bonds play an important role to stabilize the E configuration of the azomethine olefinic bond (Table 1). The crystal structure (Fig. 2) is stabilized by intermolecular O3—H2B···O4 and O2—H3A···O1 interactions to form a three-dimensional network.

Related literature top

For applications and biological activity of Schiff bases, see: Khan et al. (2011, 2012); Rada & Leto (2008); Almasirad et al. (2006). For related structures, see: Taha et al. (2012); Shen et al. (2012).

Experimental top

The title compound was synthesized by refluxing a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol) and 2,4,6-trihydroxy-5-methoxybenzaldehyde (0.304 g, 2 mmol) in methanol along with a catalytical amount of acetic acid for 3 h. The progress of reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated by vacuum to afford the crude product which was recrystallized by dissolving in methanol at room temperature. Needle-shaped crystals were obtained on slow evaporation of the solvent (0.496 g, 82% yield). All chemicals were purchased by Sigma Aldrich, Germany.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. Crystal packing of the title compound viewed down the a axis. Only hydrogen atoms involved in hydrogen bonding are shown.

(E)-2-Methoxy-N'-(2,4,6-trihydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₅	F(000) = 632
M_r = 302.28	D_x = 1.414 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3988 reflections
a = 6.4580 (4) Å	θ = 2.5–27.8°
b = 13.4772 (8) Å	µ = 0.11 mm⁻¹
c = 16.3169 (9) Å	T = 273 K
V = 1420.15 (14) Å³	Block, colourless
Z = 4	0.34 × 0.23 × 0.21 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2643 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scan	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→7
T_min = 0.964, T_max = 0.978	k = −16→16
8414 measured reflections	l = −19→19

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0444P)² + 0.1141P] where P = (F_o² + 2F_c²)/3
2643 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₅	V = 1420.15 (14) Å³
M_r = 302.28	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.4580 (4) Å	µ = 0.11 mm⁻¹
b = 13.4772 (8) Å	T = 273 K
c = 16.3169 (9) Å	0.34 × 0.23 × 0.21 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2643 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2481 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.978	R_int = 0.019
8414 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.13 e Å⁻³
2643 reflections	Δρ_min = −0.13 e Å⁻³
216 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
O1	0.5330 (2)	0.22125 (9)	0.11606 (8)	0.0543 (3)
O2	1.1070 (2)	0.40655 (9)	0.02009 (8)	0.0578 (3)
H3A	1.091 (5)	0.3604 (19)	−0.0222 (16)	0.100 (8)*
O3	0.6905 (2)	0.53380 (9)	0.23545 (7)	0.0511 (3)
H2B	0.785 (3)	0.5781 (16)	0.2396 (12)	0.065 (7)*
O4	0.0021 (2)	0.16307 (8)	0.25569 (7)	0.0518 (3)
O5	−0.0653 (2)	0.42748 (8)	0.38286 (8)	0.0578 (3)
N1	0.2953 (2)	0.30535 (10)	0.22647 (8)	0.0421 (3)
N2	0.1262 (2)	0.31688 (11)	0.27673 (8)	0.0436 (3)
H2A	0.111 (3)	0.3735 (14)	0.2990 (11)	0.054 (5)*
C1	0.6522 (2)	0.30443 (11)	0.12072 (9)	0.0403 (3)
C2	0.8209 (3)	0.31059 (12)	0.06945 (10)	0.0447 (4)
H2C	0.8508	0.2594	0.0331	0.054*
C3	0.9454 (3)	0.39399 (11)	0.07272 (9)	0.0419 (4)
C4	0.9087 (2)	0.46946 (11)	0.12866 (9)	0.0410 (3)
H4A	0.9973	0.5238	0.1318	0.049*
C5	0.7383 (2)	0.46267 (10)	0.17972 (9)	0.0382 (3)
C6	0.6031 (2)	0.38110 (11)	0.17590 (9)	0.0377 (3)
C7	0.4203 (3)	0.37914 (12)	0.22646 (9)	0.0411 (3)
H7A	0.3922	0.4331	0.2602	0.049*
C8	−0.0127 (2)	0.24489 (11)	0.28886 (9)	0.0385 (3)
C9	−0.1900 (2)	0.26844 (11)	0.34441 (9)	0.0376 (3)
C10	−0.3409 (3)	0.19578 (12)	0.35197 (10)	0.0448 (4)
H10A	−0.3256	0.1368	0.3231	0.054*
C11	−0.5130 (3)	0.20830 (14)	0.40098 (10)	0.0521 (4)
H11A	−0.6111	0.1581	0.4055	0.063*
C12	−0.5376 (3)	0.29535 (14)	0.44283 (10)	0.0550 (5)
H12A	−0.6537	0.3043	0.4758	0.066*
C13	−0.3922 (3)	0.37023 (14)	0.43680 (10)	0.0512 (4)
H13A	−0.4119	0.4295	0.4650	0.061*
C14	−0.2165 (3)	0.35718 (12)	0.38868 (9)	0.0431 (4)
C15	−0.0887 (4)	0.52036 (14)	0.42409 (13)	0.0725 (6)
H15A	0.0214	0.5642	0.4082	0.109*
H15B	−0.0837	0.5099	0.4823	0.109*
H15C	−0.2194	0.5494	0.4096	0.109*
H1A	0.432 (4)	0.2267 (18)	0.1484 (15)	0.094 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0576 (8)	0.0517 (7)	0.0535 (7)	−0.0166 (6)	0.0105 (6)	−0.0109 (5)
O2	0.0546 (8)	0.0572 (7)	0.0615 (7)	−0.0047 (6)	0.0220 (7)	−0.0072 (6)
O3	0.0522 (8)	0.0449 (7)	0.0562 (7)	−0.0059 (6)	0.0124 (6)	−0.0104 (5)
O4	0.0498 (7)	0.0414 (6)	0.0640 (7)	0.0035 (5)	0.0084 (6)	−0.0035 (5)
O5	0.0560 (8)	0.0481 (6)	0.0692 (8)	−0.0065 (6)	0.0153 (7)	−0.0140 (6)
N1	0.0348 (7)	0.0485 (7)	0.0429 (7)	0.0014 (6)	0.0043 (6)	0.0031 (6)
N2	0.0360 (7)	0.0438 (7)	0.0509 (8)	0.0004 (6)	0.0083 (6)	−0.0015 (6)
C1	0.0416 (9)	0.0404 (7)	0.0388 (7)	−0.0034 (7)	−0.0035 (7)	0.0019 (6)
C2	0.0500 (10)	0.0429 (8)	0.0411 (8)	0.0020 (8)	0.0065 (7)	−0.0041 (6)
C3	0.0387 (9)	0.0456 (8)	0.0416 (8)	0.0031 (7)	0.0052 (7)	0.0058 (6)
C4	0.0411 (9)	0.0375 (7)	0.0444 (8)	−0.0031 (7)	0.0017 (7)	0.0022 (6)
C5	0.0405 (8)	0.0375 (7)	0.0365 (7)	0.0049 (7)	−0.0005 (7)	0.0021 (6)
C6	0.0362 (8)	0.0416 (8)	0.0354 (7)	0.0020 (7)	−0.0004 (7)	0.0043 (6)
C7	0.0388 (9)	0.0448 (8)	0.0396 (8)	0.0021 (7)	0.0009 (7)	0.0021 (6)
C8	0.0355 (8)	0.0398 (8)	0.0401 (7)	0.0060 (7)	−0.0030 (7)	0.0061 (6)
C9	0.0341 (8)	0.0421 (8)	0.0366 (7)	0.0034 (6)	−0.0015 (6)	0.0057 (6)
C10	0.0418 (9)	0.0471 (8)	0.0453 (8)	−0.0014 (7)	−0.0017 (7)	0.0050 (7)
C11	0.0427 (10)	0.0657 (11)	0.0480 (9)	−0.0100 (9)	0.0030 (8)	0.0080 (8)
C12	0.0410 (10)	0.0777 (12)	0.0462 (9)	0.0026 (9)	0.0109 (8)	0.0080 (8)
C13	0.0520 (11)	0.0583 (10)	0.0433 (8)	0.0049 (9)	0.0070 (8)	−0.0027 (7)
C14	0.0408 (9)	0.0484 (8)	0.0403 (8)	0.0006 (7)	0.0002 (7)	0.0037 (7)
C15	0.0877 (16)	0.0541 (11)	0.0757 (12)	−0.0109 (11)	0.0154 (12)	−0.0200 (9)

Geometric parameters (Å, º) top

O1—C1	1.3622 (18)	C4—H4A	0.9300
O1—H1A	0.84 (3)	C5—C6	1.405 (2)
O2—C3	1.362 (2)	C6—C7	1.440 (2)
O2—H3A	0.93 (3)	C7—H7A	0.9300
O3—C5	1.3569 (18)	C8—C9	1.494 (2)
O3—H2B	0.86 (2)	C9—C10	1.387 (2)
O4—C8	1.2321 (19)	C9—C14	1.408 (2)
O5—C14	1.364 (2)	C10—C11	1.379 (2)
O5—C15	1.429 (2)	C10—H10A	0.9300
N1—C7	1.281 (2)	C11—C12	1.367 (3)
N1—N2	1.3742 (18)	C11—H11A	0.9300
N2—C8	1.336 (2)	C12—C13	1.382 (3)
N2—H2A	0.851 (19)	C12—H12A	0.9300
C1—C2	1.376 (2)	C13—C14	1.391 (2)
C1—C6	1.407 (2)	C13—H13A	0.9300
C2—C3	1.383 (2)	C15—H15A	0.9600
C2—H2C	0.9300	C15—H15B	0.9600
C3—C4	1.387 (2)	C15—H15C	0.9600
C4—C5	1.384 (2)

C1—O1—H1A	109.3 (17)	C6—C7—H7A	119.0
C3—O2—H3A	107.3 (17)	O4—C8—N2	122.19 (14)
C5—O3—H2B	112.6 (14)	O4—C8—C9	121.05 (14)
C14—O5—C15	120.00 (14)	N2—C8—C9	116.75 (13)
C7—N1—N2	114.39 (13)	C10—C9—C14	117.96 (14)
C8—N2—N1	122.66 (13)	C10—C9—C8	116.26 (13)
C8—N2—H2A	120.7 (14)	C14—C9—C8	125.78 (14)
N1—N2—H2A	116.6 (14)	C11—C10—C9	122.09 (16)
O1—C1—C2	117.59 (14)	C11—C10—H10A	119.0
O1—C1—C6	120.85 (14)	C9—C10—H10A	119.0
C2—C1—C6	121.56 (14)	C12—C11—C10	119.24 (16)
C1—C2—C3	119.07 (14)	C12—C11—H11A	120.4
C1—C2—H2C	120.5	C10—C11—H11A	120.4
C3—C2—H2C	120.5	C11—C12—C13	120.80 (16)
O2—C3—C2	121.47 (14)	C11—C12—H12A	119.6
O2—C3—C4	117.05 (14)	C13—C12—H12A	119.6
C2—C3—C4	121.47 (14)	C12—C13—C14	120.14 (16)
C5—C4—C3	118.93 (14)	C12—C13—H13A	119.9
C5—C4—H4A	120.5	C14—C13—H13A	119.9
C3—C4—H4A	120.5	O5—C14—C13	122.37 (15)
O3—C5—C4	122.54 (14)	O5—C14—C9	117.88 (14)
O3—C5—C6	116.16 (13)	C13—C14—C9	119.75 (15)
C4—C5—C6	121.29 (13)	O5—C15—H15A	109.5
C5—C6—C1	117.57 (13)	O5—C15—H15B	109.5
C5—C6—C7	119.87 (13)	H15A—C15—H15B	109.5
C1—C6—C7	122.55 (14)	O5—C15—H15C	109.5
N1—C7—C6	122.06 (14)	H15A—C15—H15C	109.5
N1—C7—H7A	119.0	H15B—C15—H15C	109.5

C7—N1—N2—C8	−175.22 (14)	N1—N2—C8—O4	0.1 (2)
O1—C1—C2—C3	−179.90 (15)	N1—N2—C8—C9	−179.32 (13)
C6—C1—C2—C3	0.4 (2)	O4—C8—C9—C10	−3.9 (2)
C1—C2—C3—O2	−176.07 (15)	N2—C8—C9—C10	175.56 (14)
C1—C2—C3—C4	2.6 (2)	O4—C8—C9—C14	176.47 (15)
O2—C3—C4—C5	175.90 (14)	N2—C8—C9—C14	−4.1 (2)
C2—C3—C4—C5	−2.8 (2)	C14—C9—C10—C11	0.0 (2)
C3—C4—C5—O3	−179.30 (14)	C8—C9—C10—C11	−179.71 (14)
C3—C4—C5—C6	0.1 (2)	C9—C10—C11—C12	0.8 (2)
O3—C5—C6—C1	−177.87 (13)	C10—C11—C12—C13	−0.3 (3)
C4—C5—C6—C1	2.7 (2)	C11—C12—C13—C14	−0.9 (3)
O3—C5—C6—C7	3.1 (2)	C15—O5—C14—C13	−2.9 (2)
C4—C5—C6—C7	−176.29 (13)	C15—O5—C14—C9	177.58 (16)
O1—C1—C6—C5	177.32 (14)	C12—C13—C14—O5	−177.81 (16)
C2—C1—C6—C5	−2.9 (2)	C12—C13—C14—C9	1.7 (2)
O1—C1—C6—C7	−3.7 (2)	C10—C9—C14—O5	178.31 (14)
C2—C1—C6—C7	176.02 (15)	C8—C9—C14—O5	−2.0 (2)
N2—N1—C7—C6	−178.41 (13)	C10—C9—C14—C13	−1.2 (2)
C5—C6—C7—N1	−178.30 (14)	C8—C9—C14—C13	178.45 (14)
C1—C6—C7—N1	2.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.84 (3)	1.88 (2)	2.6243 (18)	147 (2)
N2—H2A···O5	0.851 (19)	1.923 (19)	2.5981 (18)	135.4 (17)
O3—H2B···O4ⁱ	0.86 (2)	1.79 (2)	2.6452 (17)	175 (2)
O2—H3A···O1ⁱⁱ	0.93 (3)	1.92 (3)	2.8513 (18)	172 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₅
M_r	302.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	273
a, b, c (Å)	6.4580 (4), 13.4772 (8), 16.3169 (9)
V (Å³)	1420.15 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.34 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.964, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	8414, 2643, 2481
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.07
No. of reflections	2643
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.84 (3)	1.88 (2)	2.6243 (18)	147 (2)
N2—H2A···O5	0.851 (19)	1.923 (19)	2.5981 (18)	135.4 (17)
O3—H2B···O4ⁱ	0.86 (2)	1.79 (2)	2.6452 (17)	175 (2)
O2—H3A···O1ⁱⁱ	0.93 (3)	1.92 (3)	2.8513 (18)	172 (3)

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

References

Almasirad, A., Hosseini, R., Jalalizadeh, H., Rahimi-Moghaddam, Z., Abaeian, N., Janafrooz, M., Abbaspour, M., Ziaee, V., Dalvandi, A. & Shafiee, A. (2006). Biol. Pharm. Bull. 29, 1180–1185. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khan, K. M., Shah, Z., Ahmad, V. U., Khan, M., Taha, M., Rahim, F., Jahan, H., Perveen, S. & Choudhary, M. I. (2011). Med. Chem. 7, 572–580. Web of Science CAS PubMed Google Scholar
Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Ali, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705–710. Web of Science CAS PubMed Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Rada, B. & Leto, T. (2008). Contrib. Microbiol. 15, 164–187. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, T., Li, G. & Zheng, B. (2012). Acta Cryst. E68, o2034. CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846. CSD CrossRef IUCr Journals 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 69| Part 2| February 2013| Page o277

doi:10.1107/S1600536813001748

Open

access