(E)-N′-(2,3-Dihy­droxy­benzyl­idene)-4-meth­oxy­benzohydrazide

Promdet, P.; Horkaew, J.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536811045740

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3224

https://doi.org/10.1107/S1600536811045740

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(E)-N′-(2,3-Dihydroxybenzylidene)-4-methoxybenzohydrazide

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

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 28 October 2011; accepted 31 October 2011; online 12 November 2011)

The molecule of the title benzohydrazide derivative, C₁₅H₁₄N₂O₄, is twisted and exists in a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 56.86 (9)° and the C atom of the methoxy group deviates slightly [C—O—C—C = −10.4 (3)°] from its attached benzene ring. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by N—H⋯O and bifurcated N—H⋯(O,O) hydrogen bonds, as well as weak C—H⋯O interactions, into two-dimensional networks lying parallel to the bc plane. A weak C—H⋯π interaction also occurs.

Related literature

For background to benzohydrides and related structures, see: Fun et al. (2011 ); Horkaew et al. (2011 ). For related structures, see: Han & Zhao (2010 ); Li & Ban (2009 ). For reference bond-length data, see: Allen et al. (1987 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Monoclinic, P 2₁ /c
a = 11.6242 (15) Å
b = 9.7516 (13) Å
c = 12.6465 (16) Å
β = 96.409 (2)°
V = 1424.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 297 K
0.34 × 0.22 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.967, T_max = 0.992
13930 measured reflections
3768 independent reflections
2203 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136
S = 1.02
3768 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N2	0.88 (3)	1.86 (3)	2.6279 (18)	146 (2)
O4—H1O4⋯O1ⁱ	0.92 (2)	1.75 (2)	2.6577 (19)	170 (2)
N1—H1N1⋯O3ⁱⁱ	0.864 (19)	2.221 (19)	3.083 (2)	175.8 (17)
N1—H1N1⋯O4ⁱⁱ	0.864 (19)	2.481 (19)	2.961 (2)	115.8 (15)
C5—H5A⋯O2ⁱⁱⁱ	0.93	2.50	3.413 (2)	166
C2—H2A⋯Cg1^iv	0.93	3.00	3.539 (2)	119
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1; (iv) -x+2, -y, -z+2.

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/S1600536811045740/hb6485sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045740/hb6485Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045740/hb6485Isup3.cml

checkCIF report

Comment top

Our on-going research on the biological activities of benzohydrazides containing the -CO-NH-N=CH- grouping has led us to synthesize the title compound (I) in order to compare its activity with other related compounds (Fun et al., 2011; Horkaew et al., 2011). Our results found that (I) exhibits interesting antibacterial and antioxidant activities which will be reported elsewhere with other related benzohydrazide derivatives. Herein the crystal structure of (I) is reported.

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₅H₁₄N₂O₄, is twisted and exists in a trans-configuration with respect to the C8═N2 bond [1.280 (2) Å] and the torsion angle N1–N2–C8–C9 = 178.17 (15)°. The dihedral angle between the two benzene rings is 56.86 (9)°. The middle fragment is slightly twisted as indicated by the torsion angles O1–C7–N1–N2 = -0.8 (3)° and C7–N1–N2–C8 = 169.90 (16)°. The mean plane through this middle bridge (O1/C7/N1/N2/C8) makes the dihedral angles of 41.08 (11) and 16.45 (10)° with the planes of 4-methoxyphenyl and 2,3-dihydroxyphenyl rings, respectively. The two hydroxy groups of the 2,3-dihydroxyphenyl are co-planar with their attached benzene ring with the r.m.s. = 0.0214 (2) Å for the eight non H atoms. The methoxy group is slightly twisted from its attached benzene ring with the torsion angle C15–O2–C4–C3 = -10.4 (3)°. Bond distances of (I) are in normal range (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Han & Zhao, 2010; Li & Ban, 2009).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O, and O—H···O hydrogen bonds, as well as with weak C—H···O interactions (Table 1), into two dimensional networks parallel to the bc plane. A C—H···π interaction was also presented (Table 1).

Related literature top

For background to benzohydrides and related structures, see: Fun et al. (2011); Horkaew et al. (2011). For related structures, see: Han & Zhao (2010); Li & Ban (2009). For reference bond-length data, see: Allen et al. (1987). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

4-Methoxybenzohydrazide (2 mmol, 0.33 g) was dissolved in ethanol (10 ml) and a solution of 2,3-dihydroxybenzaldehyde (2 mmol, 0.28 g) in ethanol (10 ml) was then slowly added to it. The mixture was refluxed for around 5 hr. The solution was then cooled to room temperature and left to evaporate in air. The yellow solid product that appeared was collected by filtration and washed with ethanol and dried in air. Yellow blocks of the title compound were obtained after recrystalization from methanol by the slow evaporation of the solvent at room temperature after several days, Mp. 502-503 K.

Structure description top

For background to benzohydrides and related structures, see: Fun et al. (2011); Horkaew et al. (2011). For related structures, see: Han & Zhao (2010); Li & Ban (2009). For reference bond-length data, see: Allen et al. (1987). For graph-set theory, see: Bernstein et al. (1995).

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 40% probability displacement ellipsoids. Hydrogen bond is drawn as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the a-axis. Hydrogen bonds were drawn as dashed lines.

(E)-N'-(2,3-Dihydroxybenzylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₄	F(000) = 600
M_r = 286.28	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 502–503 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.6242 (15) Å	Cell parameters from 3768 reflections
b = 9.7516 (13) Å	θ = 2.6–29.0°
c = 12.6465 (16) Å	µ = 0.10 mm⁻¹
β = 96.409 (2)°	T = 297 K
V = 1424.6 (3) Å³	Block, yellow
Z = 4	0.34 × 0.22 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3768 independent reflections
Radiation source: fine-focus sealed tube	2203 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 8.33 pixels mm^-1	θ_max = 29.0°, θ_min = 2.6°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→12
T_min = 0.967, T_max = 0.992	l = −17→17
13930 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0547P)² + 0.2931P] where P = (F_o² + 2F_c²)/3
3768 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄	V = 1424.6 (3) Å³
M_r = 286.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6242 (15) Å	µ = 0.10 mm⁻¹
b = 9.7516 (13) Å	T = 297 K
c = 12.6465 (16) Å	0.34 × 0.22 × 0.08 mm
β = 96.409 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3768 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2203 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.992	R_int = 0.037
13930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
3768 reflections	Δρ_min = −0.18 e Å⁻³
203 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	0.76198 (12)	0.03025 (16)	1.01358 (9)	0.0644 (4)
O2	0.52798 (13)	−0.17500 (15)	0.56417 (11)	0.0716 (4)
O3	0.95302 (12)	0.31125 (15)	1.18591 (10)	0.0573 (4)
H1O3	0.919 (2)	0.266 (3)	1.131 (2)	0.105 (9)*
O4	1.07704 (14)	0.45742 (15)	1.33066 (10)	0.0655 (4)
H1O4	1.134 (2)	0.491 (2)	1.380 (2)	0.092 (8)*
N1	0.86300 (14)	0.15397 (15)	0.90461 (11)	0.0472 (4)
H1N1	0.8895 (16)	0.1593 (18)	0.8436 (15)	0.050 (5)*
N2	0.92453 (13)	0.21946 (15)	0.98936 (10)	0.0457 (4)
C1	0.71751 (15)	−0.00089 (18)	0.82727 (13)	0.0432 (4)
C2	0.68810 (17)	−0.13814 (19)	0.82957 (15)	0.0574 (5)
H2A	0.7107	−0.1896	0.8903	0.069*
C3	0.62568 (18)	−0.2001 (2)	0.74317 (17)	0.0621 (5)
H3A	0.6080	−0.2930	0.7453	0.075*
C4	0.58959 (16)	−0.12397 (19)	0.65375 (14)	0.0516 (5)
C5	0.61520 (18)	0.0146 (2)	0.65158 (14)	0.0548 (5)
H5A	0.5883	0.0672	0.5926	0.066*
C6	0.68036 (17)	0.07452 (19)	0.73656 (13)	0.0514 (5)
H6A	0.6999	0.1668	0.7334	0.062*
C7	0.78258 (15)	0.06096 (18)	0.92317 (12)	0.0445 (4)
C8	1.01140 (16)	0.29144 (17)	0.96886 (13)	0.0451 (4)
H8A	1.0311	0.2950	0.8996	0.054*
C9	1.07959 (15)	0.36759 (16)	1.05231 (12)	0.0417 (4)
C10	1.04835 (15)	0.37551 (17)	1.15543 (13)	0.0426 (4)
C11	1.11564 (16)	0.45196 (17)	1.23312 (13)	0.0464 (4)
C12	1.21434 (17)	0.51668 (18)	1.20748 (15)	0.0525 (5)
H12A	1.2599	0.5662	1.2593	0.063*
C13	1.24602 (18)	0.50867 (19)	1.10575 (16)	0.0569 (5)
H13A	1.3128	0.5527	1.0894	0.068*
C14	1.17932 (17)	0.43587 (18)	1.02824 (14)	0.0512 (5)
H14A	1.2006	0.4321	0.9596	0.061*
C15	0.5152 (2)	−0.3199 (2)	0.5548 (2)	0.0828 (7)
H15A	0.4773	−0.3422	0.4856	0.124*
H15B	0.4697	−0.3528	0.6083	0.124*
H15C	0.5902	−0.3624	0.5642	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0620 (9)	0.0923 (11)	0.0369 (6)	−0.0148 (8)	−0.0038 (6)	0.0134 (6)
O2	0.0770 (11)	0.0673 (9)	0.0646 (9)	−0.0017 (8)	−0.0194 (7)	−0.0185 (7)
O3	0.0611 (9)	0.0729 (9)	0.0388 (6)	−0.0241 (7)	0.0097 (6)	−0.0122 (6)
O4	0.0805 (11)	0.0773 (10)	0.0381 (7)	−0.0266 (8)	0.0033 (7)	−0.0101 (6)
N1	0.0545 (10)	0.0569 (9)	0.0299 (7)	−0.0064 (7)	0.0029 (6)	−0.0053 (6)
N2	0.0505 (9)	0.0523 (8)	0.0330 (7)	−0.0019 (7)	−0.0011 (6)	−0.0064 (6)
C1	0.0434 (10)	0.0478 (9)	0.0371 (8)	0.0021 (8)	−0.0017 (7)	0.0014 (7)
C2	0.0612 (13)	0.0513 (11)	0.0557 (11)	0.0040 (9)	−0.0112 (9)	0.0120 (8)
C3	0.0671 (14)	0.0444 (10)	0.0707 (12)	−0.0024 (9)	−0.0107 (10)	0.0010 (9)
C4	0.0473 (11)	0.0560 (11)	0.0494 (10)	0.0029 (9)	−0.0036 (8)	−0.0099 (8)
C5	0.0683 (13)	0.0549 (11)	0.0381 (9)	0.0039 (9)	−0.0073 (8)	0.0027 (8)
C6	0.0685 (13)	0.0455 (10)	0.0381 (8)	−0.0016 (9)	−0.0036 (8)	0.0023 (7)
C7	0.0441 (10)	0.0522 (10)	0.0356 (8)	0.0049 (8)	−0.0025 (7)	0.0041 (7)
C8	0.0537 (11)	0.0469 (9)	0.0348 (8)	0.0037 (8)	0.0054 (7)	−0.0022 (7)
C9	0.0448 (10)	0.0406 (9)	0.0391 (8)	0.0025 (7)	0.0021 (7)	0.0012 (7)
C10	0.0448 (10)	0.0431 (9)	0.0392 (8)	−0.0026 (7)	0.0013 (7)	0.0008 (7)
C11	0.0555 (12)	0.0435 (9)	0.0383 (8)	−0.0038 (8)	−0.0029 (8)	0.0006 (7)
C12	0.0561 (12)	0.0438 (10)	0.0545 (10)	−0.0082 (9)	−0.0080 (9)	0.0023 (8)
C13	0.0530 (12)	0.0523 (11)	0.0654 (12)	−0.0090 (9)	0.0066 (9)	0.0067 (9)
C14	0.0554 (12)	0.0507 (10)	0.0487 (10)	−0.0017 (9)	0.0110 (9)	0.0045 (8)
C15	0.0923 (19)	0.0771 (16)	0.0788 (15)	−0.0244 (14)	0.0085 (13)	−0.0273 (13)

Geometric parameters (Å, º) top

O1—C7	1.231 (2)	C4—C5	1.385 (3)
O2—C4	1.365 (2)	C5—C6	1.374 (2)
O2—C15	1.424 (3)	C5—H5A	0.9300
O3—C10	1.365 (2)	C6—H6A	0.9300
O3—H1O3	0.88 (3)	C8—C9	1.451 (2)
O4—C11	1.360 (2)	C8—H8A	0.9300
O4—H1O4	0.91 (3)	C9—C10	1.394 (2)
N1—C7	1.342 (2)	C9—C14	1.400 (2)
N1—N2	1.3773 (18)	C10—C11	1.401 (2)
N1—H1N1	0.863 (19)	C11—C12	1.379 (3)
N2—C8	1.280 (2)	C12—C13	1.379 (3)
C1—C2	1.382 (3)	C12—H12A	0.9300
C1—C6	1.390 (2)	C13—C14	1.377 (3)
C1—C7	1.484 (2)	C13—H13A	0.9300
C2—C3	1.382 (3)	C14—H14A	0.9300
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.379 (3)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600

C4—O2—C15	118.09 (17)	N2—C8—C9	120.83 (15)
C10—O3—H1O3	108.7 (17)	N2—C8—H8A	119.6
C11—O4—H1O4	110.3 (16)	C9—C8—H8A	119.6
C7—N1—N2	119.26 (14)	C10—C9—C14	119.05 (16)
C7—N1—H1N1	121.5 (12)	C10—C9—C8	122.03 (16)
N2—N1—H1N1	117.5 (12)	C14—C9—C8	118.92 (15)
C8—N2—N1	116.72 (14)	O3—C10—C9	122.88 (15)
C2—C1—C6	118.34 (16)	O3—C10—C11	116.98 (15)
C2—C1—C7	118.75 (15)	C9—C10—C11	120.15 (16)
C6—C1—C7	122.85 (16)	O4—C11—C12	124.23 (16)
C3—C2—C1	121.08 (17)	O4—C11—C10	116.24 (16)
C3—C2—H2A	119.5	C12—C11—C10	119.52 (16)
C1—C2—H2A	119.5	C11—C12—C13	120.59 (17)
C4—C3—C2	119.86 (18)	C11—C12—H12A	119.7
C4—C3—H3A	120.1	C13—C12—H12A	119.7
C2—C3—H3A	120.1	C14—C13—C12	120.36 (18)
O2—C4—C3	124.61 (18)	C14—C13—H13A	119.8
O2—C4—C5	115.69 (17)	C12—C13—H13A	119.8
C3—C4—C5	119.71 (17)	C13—C14—C9	120.31 (17)
C6—C5—C4	120.02 (17)	C13—C14—H14A	119.8
C6—C5—H5A	120.0	C9—C14—H14A	119.8
C4—C5—H5A	120.0	O2—C15—H15A	109.5
C5—C6—C1	120.93 (17)	O2—C15—H15B	109.5
C5—C6—H6A	119.5	H15A—C15—H15B	109.5
C1—C6—H6A	119.5	O2—C15—H15C	109.5
O1—C7—N1	122.57 (16)	H15A—C15—H15C	109.5
O1—C7—C1	121.74 (17)	H15B—C15—H15C	109.5
N1—C7—C1	115.67 (14)

C7—N1—N2—C8	169.90 (16)	C6—C1—C7—N1	−40.2 (2)
C6—C1—C2—C3	1.5 (3)	N1—N2—C8—C9	178.17 (15)
C7—C1—C2—C3	178.77 (19)	N2—C8—C9—C10	−5.6 (3)
C1—C2—C3—C4	−1.4 (3)	N2—C8—C9—C14	174.85 (16)
C15—O2—C4—C3	−10.4 (3)	C14—C9—C10—O3	−179.49 (16)
C15—O2—C4—C5	170.0 (2)	C8—C9—C10—O3	1.0 (3)
C2—C3—C4—O2	179.78 (19)	C14—C9—C10—C11	0.6 (3)
C2—C3—C4—C5	−0.6 (3)	C8—C9—C10—C11	−178.97 (16)
O2—C4—C5—C6	−177.74 (19)	O3—C10—C11—O4	−1.8 (2)
C3—C4—C5—C6	2.6 (3)	C9—C10—C11—O4	178.15 (16)
C4—C5—C6—C1	−2.6 (3)	O3—C10—C11—C12	178.61 (16)
C2—C1—C6—C5	0.5 (3)	C9—C10—C11—C12	−1.5 (3)
C7—C1—C6—C5	−176.62 (18)	O4—C11—C12—C13	−178.43 (18)
N2—N1—C7—O1	−0.8 (3)	C10—C11—C12—C13	1.1 (3)
N2—N1—C7—C1	177.88 (14)	C11—C12—C13—C14	0.0 (3)
C2—C1—C7—O1	−38.7 (3)	C12—C13—C14—C9	−0.9 (3)
C6—C1—C7—O1	138.5 (2)	C10—C9—C14—C13	0.6 (3)
C2—C1—C7—N1	142.68 (18)	C8—C9—C14—C13	−179.82 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2	0.88 (3)	1.86 (3)	2.6279 (18)	146 (2)
O4—H1O4···O1ⁱ	0.92 (2)	1.75 (2)	2.6577 (19)	170 (2)
N1—H1N1···O3ⁱⁱ	0.864 (19)	2.221 (19)	3.083 (2)	175.8 (17)
N1—H1N1···O4ⁱⁱ	0.864 (19)	2.481 (19)	2.961 (2)	115.8 (15)
C5—H5A···O2ⁱⁱⁱ	0.93	2.50	3.413 (2)	166
C2—H2A···Cg1^iv	0.93	3.00	3.539 (2)	119

Symmetry codes: (i) −x+2, y+1/2, −z+5/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄
M_r	286.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	11.6242 (15), 9.7516 (13), 12.6465 (16)
β (°)	96.409 (2)
V (Å³)	1424.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.22 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.967, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	13930, 3768, 2203
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 1.02
No. of reflections	3768
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2	0.88 (3)	1.86 (3)	2.6279 (18)	146 (2)
O4—H1O4···O1ⁱ	0.92 (2)	1.75 (2)	2.6577 (19)	170 (2)
N1—H1N1···O3ⁱⁱ	0.864 (19)	2.221 (19)	3.083 (2)	175.8 (17)
N1—H1N1···O4ⁱⁱ	0.864 (19)	2.481 (19)	2.961 (2)	115.8 (15)
C5—H5A···O2ⁱⁱⁱ	0.93	2.50	3.413 (2)	166
C2—H2A···Cg1^iv	0.93	3.00	3.539 (2)	119

Symmetry codes: (i) −x+2, y+1/2, −z+5/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

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

Acknowledgements

PP thanks the Development and Promotion of Science and Technology Talents Project for a fellowship. PP and JH thank the Crystal Materials Research Unit, 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. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for the bacterial assay.

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. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1041. Web of Science 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
Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o876. 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

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