organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Fun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644-o2645.]); Horkaew et al. (2011[Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o2985.]). For related structures, see: Han & Zhao (2010[Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1041.]); Li & Ban (2009[Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o876.]). For reference bond-length data, see: Allen et al. (1987[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.]). For graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O4

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.992

  • 13930 measured reflections

  • 3768 independent reflections

  • 2203 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −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 DA 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—H2ACg1iv 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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 C8N2 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.

Refinement top

Amide and hydroxy H atoms were located from the difference maps and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C-H) = 0.93 Å for aromatic and CH and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.72 Å from C9 and the deepest hole is located at 1.02 Å from C3.

Structure description 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 C8N2 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).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids. Hydrogen bond is drawn as a dashed line.
[Figure 2] 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
C15H14N2O4F(000) = 600
Mr = 286.28Dx = 1.335 Mg m3
Monoclinic, P21/cMelting point = 502–503 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.6242 (15) ÅCell parameters from 3768 reflections
b = 9.7516 (13) Åθ = 2.6–29.0°
c = 12.6465 (16) ŵ = 0.10 mm1
β = 96.409 (2)°T = 297 K
V = 1424.6 (3) Å3Block, yellow
Z = 40.34 × 0.22 × 0.08 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3768 independent reflections
Radiation source: fine-focus sealed tube2203 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 8.33 pixels mm-1θmax = 29.0°, θmin = 2.6°
ω scansh = 1415
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1312
Tmin = 0.967, Tmax = 0.992l = 1717
13930 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2931P]
where P = (Fo2 + 2Fc2)/3
3768 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C15H14N2O4V = 1424.6 (3) Å3
Mr = 286.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.6242 (15) ŵ = 0.10 mm1
b = 9.7516 (13) ÅT = 297 K
c = 12.6465 (16) Å0.34 × 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)
Tmin = 0.967, Tmax = 0.992Rint = 0.037
13930 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.20 e Å3
3768 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
O10.76198 (12)0.03025 (16)1.01358 (9)0.0644 (4)
O20.52798 (13)0.17500 (15)0.56417 (11)0.0716 (4)
O30.95302 (12)0.31125 (15)1.18591 (10)0.0573 (4)
H1O30.919 (2)0.266 (3)1.131 (2)0.105 (9)*
O41.07704 (14)0.45742 (15)1.33066 (10)0.0655 (4)
H1O41.134 (2)0.491 (2)1.380 (2)0.092 (8)*
N10.86300 (14)0.15397 (15)0.90461 (11)0.0472 (4)
H1N10.8895 (16)0.1593 (18)0.8436 (15)0.050 (5)*
N20.92453 (13)0.21946 (15)0.98936 (10)0.0457 (4)
C10.71751 (15)0.00089 (18)0.82727 (13)0.0432 (4)
C20.68810 (17)0.13814 (19)0.82957 (15)0.0574 (5)
H2A0.71070.18960.89030.069*
C30.62568 (18)0.2001 (2)0.74317 (17)0.0621 (5)
H3A0.60800.29300.74530.075*
C40.58959 (16)0.12397 (19)0.65375 (14)0.0516 (5)
C50.61520 (18)0.0146 (2)0.65158 (14)0.0548 (5)
H5A0.58830.06720.59260.066*
C60.68036 (17)0.07452 (19)0.73656 (13)0.0514 (5)
H6A0.69990.16680.73340.062*
C70.78258 (15)0.06096 (18)0.92317 (12)0.0445 (4)
C81.01140 (16)0.29144 (17)0.96886 (13)0.0451 (4)
H8A1.03110.29500.89960.054*
C91.07959 (15)0.36759 (16)1.05231 (12)0.0417 (4)
C101.04835 (15)0.37551 (17)1.15543 (13)0.0426 (4)
C111.11564 (16)0.45196 (17)1.23312 (13)0.0464 (4)
C121.21434 (17)0.51668 (18)1.20748 (15)0.0525 (5)
H12A1.25990.56621.25930.063*
C131.24602 (18)0.50867 (19)1.10575 (16)0.0569 (5)
H13A1.31280.55271.08940.068*
C141.17932 (17)0.43587 (18)1.02824 (14)0.0512 (5)
H14A1.20060.43210.95960.061*
C150.5152 (2)0.3199 (2)0.5548 (2)0.0828 (7)
H15A0.47730.34220.48560.124*
H15B0.46970.35280.60830.124*
H15C0.59020.36240.56420.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0620 (9)0.0923 (11)0.0369 (6)0.0148 (8)0.0038 (6)0.0134 (6)
O20.0770 (11)0.0673 (9)0.0646 (9)0.0017 (8)0.0194 (7)0.0185 (7)
O30.0611 (9)0.0729 (9)0.0388 (6)0.0241 (7)0.0097 (6)0.0122 (6)
O40.0805 (11)0.0773 (10)0.0381 (7)0.0266 (8)0.0033 (7)0.0101 (6)
N10.0545 (10)0.0569 (9)0.0299 (7)0.0064 (7)0.0029 (6)0.0053 (6)
N20.0505 (9)0.0523 (8)0.0330 (7)0.0019 (7)0.0011 (6)0.0064 (6)
C10.0434 (10)0.0478 (9)0.0371 (8)0.0021 (8)0.0017 (7)0.0014 (7)
C20.0612 (13)0.0513 (11)0.0557 (11)0.0040 (9)0.0112 (9)0.0120 (8)
C30.0671 (14)0.0444 (10)0.0707 (12)0.0024 (9)0.0107 (10)0.0010 (9)
C40.0473 (11)0.0560 (11)0.0494 (10)0.0029 (9)0.0036 (8)0.0099 (8)
C50.0683 (13)0.0549 (11)0.0381 (9)0.0039 (9)0.0073 (8)0.0027 (8)
C60.0685 (13)0.0455 (10)0.0381 (8)0.0016 (9)0.0036 (8)0.0023 (7)
C70.0441 (10)0.0522 (10)0.0356 (8)0.0049 (8)0.0025 (7)0.0041 (7)
C80.0537 (11)0.0469 (9)0.0348 (8)0.0037 (8)0.0054 (7)0.0022 (7)
C90.0448 (10)0.0406 (9)0.0391 (8)0.0025 (7)0.0021 (7)0.0012 (7)
C100.0448 (10)0.0431 (9)0.0392 (8)0.0026 (7)0.0013 (7)0.0008 (7)
C110.0555 (12)0.0435 (9)0.0383 (8)0.0038 (8)0.0029 (8)0.0006 (7)
C120.0561 (12)0.0438 (10)0.0545 (10)0.0082 (9)0.0080 (9)0.0023 (8)
C130.0530 (12)0.0523 (11)0.0654 (12)0.0090 (9)0.0066 (9)0.0067 (9)
C140.0554 (12)0.0507 (10)0.0487 (10)0.0017 (9)0.0110 (9)0.0045 (8)
C150.0923 (19)0.0771 (16)0.0788 (15)0.0244 (14)0.0085 (13)0.0273 (13)
Geometric parameters (Å, º) top
O1—C71.231 (2)C4—C51.385 (3)
O2—C41.365 (2)C5—C61.374 (2)
O2—C151.424 (3)C5—H5A0.9300
O3—C101.365 (2)C6—H6A0.9300
O3—H1O30.88 (3)C8—C91.451 (2)
O4—C111.360 (2)C8—H8A0.9300
O4—H1O40.91 (3)C9—C101.394 (2)
N1—C71.342 (2)C9—C141.400 (2)
N1—N21.3773 (18)C10—C111.401 (2)
N1—H1N10.863 (19)C11—C121.379 (3)
N2—C81.280 (2)C12—C131.379 (3)
C1—C21.382 (3)C12—H12A0.9300
C1—C61.390 (2)C13—C141.377 (3)
C1—C71.484 (2)C13—H13A0.9300
C2—C31.382 (3)C14—H14A0.9300
C2—H2A0.9300C15—H15A0.9600
C3—C41.379 (3)C15—H15B0.9600
C3—H3A0.9300C15—H15C0.9600
C4—O2—C15118.09 (17)N2—C8—C9120.83 (15)
C10—O3—H1O3108.7 (17)N2—C8—H8A119.6
C11—O4—H1O4110.3 (16)C9—C8—H8A119.6
C7—N1—N2119.26 (14)C10—C9—C14119.05 (16)
C7—N1—H1N1121.5 (12)C10—C9—C8122.03 (16)
N2—N1—H1N1117.5 (12)C14—C9—C8118.92 (15)
C8—N2—N1116.72 (14)O3—C10—C9122.88 (15)
C2—C1—C6118.34 (16)O3—C10—C11116.98 (15)
C2—C1—C7118.75 (15)C9—C10—C11120.15 (16)
C6—C1—C7122.85 (16)O4—C11—C12124.23 (16)
C3—C2—C1121.08 (17)O4—C11—C10116.24 (16)
C3—C2—H2A119.5C12—C11—C10119.52 (16)
C1—C2—H2A119.5C11—C12—C13120.59 (17)
C4—C3—C2119.86 (18)C11—C12—H12A119.7
C4—C3—H3A120.1C13—C12—H12A119.7
C2—C3—H3A120.1C14—C13—C12120.36 (18)
O2—C4—C3124.61 (18)C14—C13—H13A119.8
O2—C4—C5115.69 (17)C12—C13—H13A119.8
C3—C4—C5119.71 (17)C13—C14—C9120.31 (17)
C6—C5—C4120.02 (17)C13—C14—H14A119.8
C6—C5—H5A120.0C9—C14—H14A119.8
C4—C5—H5A120.0O2—C15—H15A109.5
C5—C6—C1120.93 (17)O2—C15—H15B109.5
C5—C6—H6A119.5H15A—C15—H15B109.5
C1—C6—H6A119.5O2—C15—H15C109.5
O1—C7—N1122.57 (16)H15A—C15—H15C109.5
O1—C7—C1121.74 (17)H15B—C15—H15C109.5
N1—C7—C1115.67 (14)
C7—N1—N2—C8169.90 (16)C6—C1—C7—N140.2 (2)
C6—C1—C2—C31.5 (3)N1—N2—C8—C9178.17 (15)
C7—C1—C2—C3178.77 (19)N2—C8—C9—C105.6 (3)
C1—C2—C3—C41.4 (3)N2—C8—C9—C14174.85 (16)
C15—O2—C4—C310.4 (3)C14—C9—C10—O3179.49 (16)
C15—O2—C4—C5170.0 (2)C8—C9—C10—O31.0 (3)
C2—C3—C4—O2179.78 (19)C14—C9—C10—C110.6 (3)
C2—C3—C4—C50.6 (3)C8—C9—C10—C11178.97 (16)
O2—C4—C5—C6177.74 (19)O3—C10—C11—O41.8 (2)
C3—C4—C5—C62.6 (3)C9—C10—C11—O4178.15 (16)
C4—C5—C6—C12.6 (3)O3—C10—C11—C12178.61 (16)
C2—C1—C6—C50.5 (3)C9—C10—C11—C121.5 (3)
C7—C1—C6—C5176.62 (18)O4—C11—C12—C13178.43 (18)
N2—N1—C7—O10.8 (3)C10—C11—C12—C131.1 (3)
N2—N1—C7—C1177.88 (14)C11—C12—C13—C140.0 (3)
C2—C1—C7—O138.7 (3)C12—C13—C14—C90.9 (3)
C6—C1—C7—O1138.5 (2)C10—C9—C14—C130.6 (3)
C2—C1—C7—N1142.68 (18)C8—C9—C14—C13179.82 (17)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C9–C14 ring.
D—H···AD—HH···AD···AD—H···A
O3—H1O3···N20.88 (3)1.86 (3)2.6279 (18)146 (2)
O4—H1O4···O1i0.92 (2)1.75 (2)2.6577 (19)170 (2)
N1—H1N1···O3ii0.864 (19)2.221 (19)3.083 (2)175.8 (17)
N1—H1N1···O4ii0.864 (19)2.481 (19)2.961 (2)115.8 (15)
C5—H5A···O2iii0.932.503.413 (2)166
C2—H2A···Cg1iv0.933.003.539 (2)119
Symmetry codes: (i) x+2, y+1/2, z+5/2; (ii) x, y+1/2, z1/2; (iii) x+1, y, z+1; (iv) x+2, y, z+2.

Experimental details

Crystal data
Chemical formulaC15H14N2O4
Mr286.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)297
a, b, c (Å)11.6242 (15), 9.7516 (13), 12.6465 (16)
β (°) 96.409 (2)
V3)1424.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.34 × 0.22 × 0.08
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.967, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
13930, 3768, 2203
Rint0.037
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.136, 1.02
No. of reflections3768
No. of parameters203
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O3—H1O3···N20.88 (3)1.86 (3)2.6279 (18)146 (2)
O4—H1O4···O1i0.92 (2)1.75 (2)2.6577 (19)170 (2)
N1—H1N1···O3ii0.864 (19)2.221 (19)3.083 (2)175.8 (17)
N1—H1N1···O4ii0.864 (19)2.481 (19)2.961 (2)115.8 (15)
C5—H5A···O2iii0.932.503.413 (2)166
C2—H2A···Cg1iv0.933.003.539 (2)119
Symmetry codes: (i) x+2, y+1/2, z+5/2; (ii) x, y+1/2, z1/2; (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

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