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ISSN: 2056-9890

(E)-1-(2,4-Di­nitro­phen­yl)-2-[1-(3-meth­­oxy­phen­yl)ethyl­­idene]hydrazine

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my

(Received 28 May 2012; accepted 14 June 2012; online 20 June 2012)

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C15H14N4O5, with different conformations for the meth­oxy groups. The mol­ecules are both slightly twisted, the dihedral angles between two benzene rings being 8.37 (18)° in one and 7.31 (18)° in the other. In both mol­ecules, the two nitro groups are essentially coplanar with their bound benzene ring, with the r.m.s. deviation of the dinitro­benzene plane being 0.0310 (3) Å in one mol­ecule and 0.0650 (3) Å in the other. In each mol­ecule, an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions and stacked along the a axis through ππ inter­actions, with centroid–centroid distances of 3.651 (2) and 3.721 (2) Å. The crystal studied was a non-merohedral twin with a refined minor component of 20.1 (3)%.

Related literature

For 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 hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Chantrapromma et al. (2012[Chantrapromma, S., Nilwanna, B., Kobkeatthawin, T., Jansrisewangwong, P. & Fun, H.-K. (2012). Acta Cryst. E68, o1644-o1645.]); Fun et al. (2010[Fun, H.-K., Jansrisewangwong, P. & Chantrapromma, S. (2010). Acta Cryst. E66, o2401-o2402.]); Nilwanna et al. (2011[Nilwanna, B., Chantrapromma, S., Jansrisewangwong, P. & Fun, H.-K. (2011). Acta Cryst. E67, o3084-o3085.]). For background to the biological activity of hydro­zones, see: Bendre et al. (1998[Bendre, R., Murugkar, A., Padhye, S., Kulkarni, P. & Karve, M. (1998). Met. Based Drugs, 5, 59-66.]); El-Sherif (2009[El-Sherif, A. A. (2009). Inorg. Chim. Acta, 362, 4991-5000.]); Gokce et al. (2009[Gokce, M., Utku, S. & Kupeli, E. (2009). Eur. J. Med. Chem. 44, 3760-3764.]); Molyneux (2004[Molyneux, P. (2004). Songklanakarin J. Sci. Technol. 26, 211-219.]); Sathyadevi et al. (2012[Sathyadevi, P., Krishnamoorthy, P., Alagesan, M., Thanigaimani, K., Thomas, M. P. & Dharmaraj, N. (2012). Polyhedron, 31, 294-306.]); Xia et al. (2008[Xia, Y., Fan, C.-D., Zhao, B.-X., Zhao, J., Shin, D.-S. & Miao, J.-Y. (2008). Eur. J. Med. Chem. 43, 2347-2353.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N4O5

  • Mr = 330.30

  • Triclinic, [P \overline 1]

  • a = 7.5612 (13) Å

  • b = 10.4517 (18) Å

  • c = 19.516 (3) Å

  • α = 76.034 (4)°

  • β = 89.531 (4)°

  • γ = 84.052 (4)°

  • V = 1488.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.33 × 0.14 × 0.05 mm

Data collection
  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.964, Tmax = 0.994

  • 7846 measured reflections

  • 7846 independent reflections

  • 5592 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.086

  • wR(F2) = 0.296

  • S = 1.11

  • 7846 reflections

  • 444 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.59 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1NA⋯O1A 0.87 (3) 1.94 (4) 2.611 (4) 133 (3)
N1B—H1NB⋯O1B 0.88 (4) 1.96 (3) 2.611 (4) 130 (4)
C5B—H5B⋯O3Ai 0.93 2.59 3.462 (5) 156
C6B—H6B⋯O4Ai 0.93 2.50 3.277 (4) 141
C8A—H8C⋯O3Bii 0.96 2.57 3.376 (5) 142
C8B—H8E⋯O4Biii 0.96 2.45 3.402 (5) 170
C12B—H12B⋯O2Aiv 0.93 2.57 3.447 (5) 157
C13A—H13A⋯O3Biii 0.93 2.48 3.204 (5) 135
C13B—H13B⋯O3Aiv 0.93 2.55 3.448 (5) 162
C14B—H14B⋯O4Biii 0.93 2.47 3.338 (5) 155
C15B—H15E⋯O3Av 0.96 2.57 3.301 (5) 133
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y, -z+1; (iii) x-1, y+1, z; (iv) x-1, y+1, z-1; (v) -x+1, -y+1, -z+1.

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

Hydrazones are important compounds which have considerable interesting applications involving biological activities such as antibacterial (El-Sherif et al., 2009), antioxidant (Sathyadevi et al., 2012), anticancer (Xia et al., 2008), anti-inflammatory (Gokce et al., 2009) and tyrosinase inhibitory (Bendre et al., 1998) activities. With our on-going research on crystal structures, bioactivity and antioxidant activity of hydrazones (Chantrapromma et al., 2012; Fun et al., 2010; Nilwanna et al., 2011), the title compound (I) was synthesized. The evaluation of its antioxidant activity by DPPH scavenging (Molyneux, 2004) was found to be inactive. Herein we report the synthesis and crystal structure of (I).

In Fig. 1, there are two crystallographically independent molecules A and B in the asymmetric unit of (I), C15H14N4O5, with differences in bond angles and conformations of the methoxy groups in which in molecule A the methoxy group is co-planar with its bound benzene ring and pointed toward the central ethylidenehydrazine (N1/N2/C7/C8) as indicated by the torsion angle C15A–O5A–C11A–C10A = -2.6 (5)°, whereas in molecule B it is twisted and pointed away from the central ethylidenehydrazine with the torsion angle C15B–O5B–C11B–C10B = 167.7 (3)°. The molecular structure of (I) is twisted with the dihedral angle between the two benzene rings being 8.37 (18)° in molecule A and 7.31 (18)° in molecule B. The central ethylidenehydrazine bridge is planar with the torsion angles N1–N2–C7–C8 = -1.3 (5) and 1.7 (5)° in molecules A and B, respectively. The mean plane through this central bridge makes dihedral angles of 9.0 (2) and 1.5 (2)° with the 2,4-dinitro- and 3-methoxy-substituted benzene rings, respectively, in molecule A, whereas the corresponding values are 7.8 (2) and 1.0 (2)° in molecule B. In both molecules, the two nitro groups are co-planar with their bound benzene rings with r.m.s. deviations of 0.0310 (3) and 0.0650 (3) Å in molecules A and B, respectively, for the twelve non H-atoms (C1–C6/N3/N4/O1–O4). In each molecule, intramolecular N—H···O hydrogen bonds (Fig. 1 and Table 1) generate two S(6) ring motifs (Bernstein et al., 1995). The bond distances are in normal ranges (Allen et al., 1987) and are comparable with the related structures (Chantrapromma et al., 2012; Fun et al., 2010; Nilwanna et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by weak C—H···O interactions (Table 1) and stacked along the a axis by ππ interactions with distances of Cg1···Cg4v = 3.721 (2) Å and Cg2···Cg3v = 3.651 (2) Å; Cg1, Cg2, Cg3 and Cg4 are the centroids of C1A–C6A, C9A–C14A, C1B–C6B and C9B–C14B benzene rings, respectively.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Chantrapromma et al. (2012); Fun et al. (2010); Nilwanna et al. (2011). For background to the biological activity of hydrozones, see: Bendre et al. (1998); El-Sherif (2009); Gokce et al. (2009); Molyneux (2004); Sathyadevi et al. (2012); Xia et al. (2008).

Experimental top

The title compound (I) was synthesized by dissolving 2,4-dinitrophenylhydrazine (0.40 g, 2 mmol) in ethanol (10.00 ml) and H2SO4 (conc.) (98 %, 0.50 ml) was slowly added with stirring. 3-Methoxyacetophenone (0.33 ml, 2 mmol) was then added to the solution with continuous stirring. The solution was stirred for 1 hr yielding an orange solid, which was filtered off and washed with methanol. Orange plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvent at room temperature over several days (m.p. 459-460 K).

Refinement top

Amide H atoms were located in a difference Fourier map and were refined with a distance restraint of N—H = 0.86 (2) Å and with Uiso(H) = 1.5Ueq(N). The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å for aromatic 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 crystal studied was a twin with BASF = 0.201 (3). As the twin law is non-integer, PLATON was used to convert the original data set in HKLF4 format into HKLF5 format for the final refinement. This method would reduce all the R-values of the data set to zeros. In the submission CIF, the R-values of the original data set in HKLF4 format was inputted in these fields in place of the zeros.

Structure description top

Hydrazones are important compounds which have considerable interesting applications involving biological activities such as antibacterial (El-Sherif et al., 2009), antioxidant (Sathyadevi et al., 2012), anticancer (Xia et al., 2008), anti-inflammatory (Gokce et al., 2009) and tyrosinase inhibitory (Bendre et al., 1998) activities. With our on-going research on crystal structures, bioactivity and antioxidant activity of hydrazones (Chantrapromma et al., 2012; Fun et al., 2010; Nilwanna et al., 2011), the title compound (I) was synthesized. The evaluation of its antioxidant activity by DPPH scavenging (Molyneux, 2004) was found to be inactive. Herein we report the synthesis and crystal structure of (I).

In Fig. 1, there are two crystallographically independent molecules A and B in the asymmetric unit of (I), C15H14N4O5, with differences in bond angles and conformations of the methoxy groups in which in molecule A the methoxy group is co-planar with its bound benzene ring and pointed toward the central ethylidenehydrazine (N1/N2/C7/C8) as indicated by the torsion angle C15A–O5A–C11A–C10A = -2.6 (5)°, whereas in molecule B it is twisted and pointed away from the central ethylidenehydrazine with the torsion angle C15B–O5B–C11B–C10B = 167.7 (3)°. The molecular structure of (I) is twisted with the dihedral angle between the two benzene rings being 8.37 (18)° in molecule A and 7.31 (18)° in molecule B. The central ethylidenehydrazine bridge is planar with the torsion angles N1–N2–C7–C8 = -1.3 (5) and 1.7 (5)° in molecules A and B, respectively. The mean plane through this central bridge makes dihedral angles of 9.0 (2) and 1.5 (2)° with the 2,4-dinitro- and 3-methoxy-substituted benzene rings, respectively, in molecule A, whereas the corresponding values are 7.8 (2) and 1.0 (2)° in molecule B. In both molecules, the two nitro groups are co-planar with their bound benzene rings with r.m.s. deviations of 0.0310 (3) and 0.0650 (3) Å in molecules A and B, respectively, for the twelve non H-atoms (C1–C6/N3/N4/O1–O4). In each molecule, intramolecular N—H···O hydrogen bonds (Fig. 1 and Table 1) generate two S(6) ring motifs (Bernstein et al., 1995). The bond distances are in normal ranges (Allen et al., 1987) and are comparable with the related structures (Chantrapromma et al., 2012; Fun et al., 2010; Nilwanna et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by weak C—H···O interactions (Table 1) and stacked along the a axis by ππ interactions with distances of Cg1···Cg4v = 3.721 (2) Å and Cg2···Cg3v = 3.651 (2) Å; Cg1, Cg2, Cg3 and Cg4 are the centroids of C1A–C6A, C9A–C14A, C1B–C6B and C9B–C14B benzene rings, respectively.

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Chantrapromma et al. (2012); Fun et al. (2010); Nilwanna et al. (2011). For background to the biological activity of hydrozones, see: Bendre et al. (1998); El-Sherif (2009); Gokce et al. (2009); Molyneux (2004); Sathyadevi et al. (2012); Xia et al. (2008).

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 60% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular N—H···O hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines.
(E)-1-(2,4-Dinitrophenyl)-2-[1-(3-methoxyphenyl)ethylidene]hydrazine top
Crystal data top
C15H14N4O5Z = 4
Mr = 330.30F(000) = 688
Triclinic, P1Dx = 1.474 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5612 (13) ÅCell parameters from 7846 reflections
b = 10.4517 (18) Åθ = 1.1–29.0°
c = 19.516 (3) ŵ = 0.11 mm1
α = 76.034 (4)°T = 100 K
β = 89.531 (4)°Plate, orange
γ = 84.052 (4)°0.33 × 0.14 × 0.05 mm
V = 1488.4 (4) Å3
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
7846 independent reflections
Radiation source: fine-focus sealed tube5592 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ and ω scansθmax = 29.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1010
Tmin = 0.964, Tmax = 0.994k = 1314
7846 measured reflectionsl = 1226
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.296H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.1531P)2 + 2.363P]
where P = (Fo2 + 2Fc2)/3
7846 reflections(Δ/σ)max = 0.001
444 parametersΔρmax = 0.53 e Å3
2 restraintsΔρmin = 0.59 e Å3
Crystal data top
C15H14N4O5γ = 84.052 (4)°
Mr = 330.30V = 1488.4 (4) Å3
Triclinic, P1Z = 4
a = 7.5612 (13) ÅMo Kα radiation
b = 10.4517 (18) ŵ = 0.11 mm1
c = 19.516 (3) ÅT = 100 K
α = 76.034 (4)°0.33 × 0.14 × 0.05 mm
β = 89.531 (4)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer
7846 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5592 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.994Rint = 0.000
7846 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0862 restraints
wR(F2) = 0.296H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.53 e Å3
7846 reflectionsΔρmin = 0.59 e Å3
444 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
xyzUiso*/Ueq
O1A0.5983 (4)0.0757 (3)0.79029 (14)0.0199 (6)
O2A0.7040 (4)0.0325 (3)0.89291 (14)0.0181 (6)
O3A0.6439 (4)0.1398 (3)1.09429 (14)0.0196 (6)
O4A0.4793 (4)0.3241 (3)1.09095 (15)0.0233 (6)
O5A0.0748 (4)0.8559 (3)0.67880 (16)0.0231 (6)
N1A0.4046 (4)0.3030 (3)0.77458 (15)0.0128 (6)
H1NA0.442 (6)0.238 (3)0.756 (2)0.019*
N2A0.3056 (4)0.4176 (3)0.73966 (16)0.0146 (6)
N3A0.6176 (4)0.0642 (3)0.85475 (16)0.0136 (6)
N4A0.5456 (4)0.2375 (3)1.06297 (16)0.0154 (6)
C1A0.4380 (5)0.2851 (4)0.84447 (18)0.0127 (7)
C2A0.5381 (4)0.1691 (4)0.88527 (18)0.0125 (6)
C3A0.5721 (4)0.1543 (4)0.95672 (18)0.0126 (7)
H3A0.63890.07870.98270.015*
C4A0.5064 (4)0.2520 (4)0.98843 (18)0.0128 (7)
C5A0.4078 (5)0.3681 (4)0.95041 (19)0.0152 (7)
H5A0.36430.43350.97300.018*
C6A0.3764 (5)0.3842 (4)0.87965 (18)0.0139 (7)
H6A0.31310.46200.85420.017*
C7A0.2916 (5)0.4404 (4)0.67163 (18)0.0131 (7)
C8A0.3760 (5)0.3548 (4)0.62647 (19)0.0183 (7)
H8A0.45290.28340.65520.027*
H8B0.44420.40680.59050.027*
H8C0.28530.31940.60480.027*
C9A0.1823 (5)0.5658 (4)0.63623 (18)0.0138 (7)
C10A0.1036 (5)0.6493 (4)0.67685 (19)0.0157 (7)
H10A0.11730.62560.72570.019*
C11A0.0055 (5)0.7671 (4)0.6442 (2)0.0168 (7)
C12A0.0155 (5)0.8030 (4)0.5704 (2)0.0207 (8)
H12A0.07970.88300.54830.025*
C13A0.0596 (6)0.7191 (4)0.5309 (2)0.0227 (8)
H13A0.04400.74240.48210.027*
C14A0.1580 (5)0.6005 (4)0.56287 (19)0.0189 (8)
H14A0.20750.54450.53570.023*
C15A0.0621 (5)0.8217 (4)0.7541 (2)0.0223 (8)
H15A0.13520.88620.77230.033*
H15B0.05930.82000.76860.033*
H15C0.10190.73580.77200.033*
O1B0.3655 (4)0.3835 (3)0.45297 (14)0.0202 (6)
O2B0.4931 (4)0.1929 (3)0.51179 (14)0.0258 (7)
O3B0.8328 (4)0.0989 (3)0.39840 (15)0.0215 (6)
O4B0.7842 (4)0.0858 (3)0.28765 (15)0.0234 (6)
O5B0.1203 (4)0.6180 (3)0.00270 (14)0.0187 (6)
N1B0.3221 (4)0.4301 (3)0.31624 (16)0.0150 (6)
H1NB0.288 (6)0.456 (5)0.3542 (17)0.022*
N2B0.2573 (4)0.4970 (3)0.25056 (16)0.0140 (6)
N3B0.4467 (4)0.2707 (3)0.45574 (16)0.0161 (6)
N4B0.7603 (4)0.0432 (3)0.34084 (17)0.0167 (6)
C1B0.4252 (4)0.3144 (4)0.32377 (18)0.0124 (7)
C2B0.4874 (5)0.2337 (4)0.39022 (18)0.0121 (6)
C3B0.5970 (5)0.1153 (4)0.39627 (19)0.0136 (7)
H3B0.63830.06450.44020.016*
C4B0.6422 (4)0.0759 (4)0.33599 (18)0.0128 (7)
C5B0.5822 (5)0.1513 (4)0.26873 (19)0.0145 (7)
H5B0.61290.12180.22850.017*
C6B0.4787 (5)0.2677 (4)0.26357 (18)0.0131 (7)
H6B0.44180.31850.21910.016*
C7B0.1651 (4)0.6103 (4)0.24548 (18)0.0129 (7)
C8B0.1308 (5)0.6726 (4)0.3065 (2)0.0193 (8)
H8D0.10390.60610.34750.029*
H8E0.03190.73990.29520.029*
H8F0.23450.71170.31600.029*
C9B0.0979 (5)0.6790 (4)0.17307 (19)0.0136 (7)
C10B0.1345 (5)0.6197 (4)0.11704 (19)0.0144 (7)
H10B0.20000.53690.12500.017*
C11B0.0731 (5)0.6842 (4)0.0492 (2)0.0147 (7)
C12B0.0255 (5)0.8084 (4)0.0359 (2)0.0170 (7)
H12B0.06680.85090.00950.020*
C13B0.0604 (5)0.8667 (4)0.0919 (2)0.0183 (7)
H13B0.12500.94980.08380.022*
C14B0.0003 (5)0.8030 (4)0.1601 (2)0.0166 (7)
H14B0.02590.84340.19710.020*
C15B0.0306 (6)0.6672 (4)0.0701 (2)0.0216 (8)
H15D0.06300.60790.09980.032*
H15E0.06450.75350.09190.032*
H15F0.09570.67300.06350.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0298 (14)0.0200 (14)0.0094 (12)0.0053 (11)0.0047 (10)0.0060 (10)
O2A0.0204 (13)0.0123 (13)0.0192 (13)0.0049 (10)0.0053 (10)0.0018 (10)
O3A0.0217 (13)0.0195 (14)0.0148 (12)0.0016 (11)0.0053 (10)0.0002 (11)
O4A0.0352 (16)0.0217 (15)0.0124 (12)0.0048 (12)0.0008 (11)0.0064 (11)
O5A0.0258 (14)0.0187 (15)0.0221 (14)0.0074 (11)0.0007 (11)0.0040 (12)
N1A0.0162 (14)0.0105 (14)0.0102 (14)0.0036 (11)0.0039 (11)0.0015 (11)
N2A0.0177 (14)0.0137 (15)0.0113 (14)0.0022 (12)0.0046 (11)0.0023 (12)
N3A0.0145 (14)0.0131 (15)0.0129 (14)0.0011 (11)0.0005 (11)0.0038 (12)
N4A0.0208 (15)0.0144 (15)0.0106 (14)0.0020 (12)0.0000 (11)0.0021 (12)
C1A0.0143 (15)0.0129 (17)0.0114 (16)0.0030 (13)0.0018 (12)0.0031 (13)
C2A0.0142 (15)0.0134 (17)0.0103 (15)0.0000 (12)0.0020 (12)0.0045 (13)
C3A0.0116 (15)0.0131 (17)0.0123 (16)0.0022 (12)0.0000 (12)0.0012 (13)
C4A0.0129 (15)0.0132 (17)0.0106 (15)0.0007 (13)0.0003 (12)0.0001 (13)
C5A0.0189 (17)0.0141 (18)0.0124 (16)0.0002 (13)0.0016 (13)0.0036 (13)
C6A0.0174 (16)0.0116 (17)0.0114 (16)0.0028 (13)0.0007 (12)0.0020 (13)
C7A0.0159 (16)0.0121 (17)0.0110 (15)0.0006 (13)0.0008 (12)0.0026 (13)
C8A0.0268 (19)0.0173 (19)0.0099 (16)0.0026 (15)0.0002 (13)0.0037 (14)
C9A0.0156 (16)0.0128 (17)0.0111 (16)0.0013 (13)0.0036 (12)0.0005 (13)
C10A0.0178 (16)0.0157 (18)0.0129 (16)0.0044 (14)0.0027 (13)0.0011 (14)
C11A0.0150 (16)0.0164 (18)0.0191 (18)0.0014 (14)0.0014 (13)0.0047 (15)
C12A0.0229 (19)0.0181 (19)0.0172 (18)0.0029 (15)0.0048 (14)0.0015 (15)
C13A0.029 (2)0.025 (2)0.0107 (17)0.0002 (16)0.0047 (14)0.0008 (15)
C14A0.0234 (18)0.021 (2)0.0103 (16)0.0003 (15)0.0016 (13)0.0021 (14)
C15A0.0220 (18)0.024 (2)0.0209 (19)0.0018 (16)0.0050 (15)0.0076 (16)
O1B0.0289 (14)0.0166 (14)0.0147 (13)0.0064 (11)0.0003 (10)0.0066 (11)
O2B0.0438 (18)0.0211 (15)0.0091 (12)0.0063 (13)0.0032 (11)0.0009 (11)
O3B0.0248 (14)0.0194 (14)0.0169 (13)0.0063 (11)0.0050 (11)0.0012 (11)
O4B0.0310 (15)0.0211 (15)0.0178 (14)0.0088 (12)0.0018 (11)0.0089 (12)
O5B0.0233 (13)0.0187 (14)0.0136 (13)0.0026 (11)0.0026 (10)0.0051 (11)
N1B0.0193 (15)0.0147 (15)0.0098 (14)0.0031 (12)0.0009 (11)0.0029 (12)
N2B0.0140 (13)0.0140 (15)0.0118 (14)0.0018 (11)0.0000 (11)0.0001 (12)
N3B0.0212 (15)0.0158 (16)0.0106 (14)0.0002 (12)0.0018 (11)0.0026 (12)
N4B0.0182 (14)0.0141 (16)0.0171 (15)0.0020 (12)0.0006 (11)0.0040 (12)
C1B0.0127 (15)0.0120 (17)0.0126 (16)0.0002 (12)0.0004 (12)0.0034 (13)
C2B0.0152 (15)0.0137 (17)0.0075 (15)0.0005 (13)0.0015 (12)0.0029 (13)
C3B0.0153 (16)0.0132 (17)0.0110 (15)0.0008 (13)0.0004 (12)0.0007 (13)
C4B0.0132 (15)0.0102 (16)0.0136 (16)0.0026 (12)0.0008 (12)0.0019 (13)
C5B0.0146 (16)0.0168 (18)0.0130 (16)0.0019 (13)0.0016 (12)0.0048 (14)
C6B0.0165 (16)0.0121 (17)0.0088 (15)0.0003 (13)0.0015 (12)0.0005 (13)
C7B0.0114 (14)0.0128 (17)0.0137 (16)0.0007 (12)0.0006 (12)0.0024 (13)
C8B0.0223 (18)0.0192 (19)0.0165 (17)0.0050 (15)0.0016 (14)0.0075 (15)
C9B0.0122 (15)0.0140 (17)0.0134 (16)0.0010 (13)0.0002 (12)0.0015 (13)
C10B0.0131 (15)0.0128 (17)0.0160 (17)0.0012 (13)0.0000 (12)0.0019 (14)
C11B0.0137 (15)0.0126 (17)0.0181 (17)0.0028 (13)0.0001 (13)0.0035 (14)
C12B0.0149 (16)0.0154 (18)0.0193 (18)0.0004 (13)0.0034 (13)0.0019 (14)
C13B0.0192 (17)0.0120 (17)0.0211 (19)0.0021 (14)0.0010 (14)0.0006 (14)
C14B0.0169 (16)0.0155 (18)0.0160 (17)0.0005 (13)0.0025 (13)0.0022 (14)
C15B0.026 (2)0.024 (2)0.0146 (17)0.0027 (16)0.0031 (14)0.0044 (15)
Geometric parameters (Å, º) top
O1A—N3A1.243 (4)O1B—N3B1.261 (4)
O2A—N3A1.229 (4)O2B—N3B1.224 (4)
O3A—N4A1.232 (4)O3B—N4B1.236 (4)
O4A—N4A1.228 (4)O4B—N4B1.230 (4)
O5A—C11A1.367 (5)O5B—C11B1.383 (5)
O5A—C15A1.427 (5)O5B—C15B1.438 (5)
N1A—C1A1.353 (4)N1B—C1B1.347 (5)
N1A—N2A1.374 (4)N1B—N2B1.370 (4)
N1A—H1NA0.868 (19)N1B—H1NB0.873 (19)
N2A—C7A1.294 (5)N2B—C7B1.293 (5)
N3A—C2A1.447 (5)N3B—C2B1.444 (4)
N4A—C4A1.456 (4)N4B—C4B1.439 (5)
C1A—C6A1.414 (5)C1B—C6B1.418 (5)
C1A—C2A1.425 (5)C1B—C2B1.419 (5)
C2A—C3A1.388 (5)C2B—C3B1.397 (5)
C3A—C4A1.367 (5)C3B—C4B1.367 (5)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.402 (5)C4B—C5B1.409 (5)
C5A—C6A1.370 (5)C5B—C6B1.360 (5)
C5A—H5A0.9300C5B—H5B0.9300
C6A—H6A0.9300C6B—H6B0.9300
C7A—C9A1.492 (5)C7B—C9B1.489 (5)
C7A—C8A1.496 (5)C7B—C8B1.498 (5)
C8A—H8A0.9600C8B—H8D0.9600
C8A—H8B0.9600C8B—H8E0.9600
C8A—H8C0.9600C8B—H8F0.9600
C9A—C14A1.398 (5)C9B—C14B1.393 (5)
C9A—C10A1.401 (5)C9B—C10B1.394 (5)
C10A—C11A1.382 (5)C10B—C11B1.393 (5)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.402 (5)C11B—C12B1.395 (5)
C12A—C13A1.380 (6)C12B—C13B1.384 (6)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.386 (6)C13B—C14B1.394 (5)
C13A—H13A0.9300C13B—H13B0.9300
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
C11A—O5A—C15A117.4 (3)C11B—O5B—C15B116.8 (3)
C1A—N1A—N2A118.3 (3)C1B—N1B—N2B119.4 (3)
C1A—N1A—H1NA117 (3)C1B—N1B—H1NB118 (3)
N2A—N1A—H1NA125 (3)N2B—N1B—H1NB122 (3)
C7A—N2A—N1A117.6 (3)C7B—N2B—N1B117.2 (3)
O2A—N3A—O1A122.0 (3)O2B—N3B—O1B122.2 (3)
O2A—N3A—C2A119.2 (3)O2B—N3B—C2B119.4 (3)
O1A—N3A—C2A118.7 (3)O1B—N3B—C2B118.4 (3)
O4A—N4A—O3A123.7 (3)O4B—N4B—O3B122.7 (3)
O4A—N4A—C4A117.9 (3)O4B—N4B—C4B118.6 (3)
O3A—N4A—C4A118.3 (3)O3B—N4B—C4B118.6 (3)
N1A—C1A—C6A120.4 (3)N1B—C1B—C6B120.2 (3)
N1A—C1A—C2A122.4 (3)N1B—C1B—C2B123.3 (3)
C6A—C1A—C2A117.2 (3)C6B—C1B—C2B116.4 (3)
C3A—C2A—C1A121.1 (3)C3B—C2B—C1B122.0 (3)
C3A—C2A—N3A116.2 (3)C3B—C2B—N3B115.6 (3)
C1A—C2A—N3A122.7 (3)C1B—C2B—N3B122.3 (3)
C4A—C3A—C2A119.3 (3)C4B—C3B—C2B118.3 (3)
C4A—C3A—H3A120.3C4B—C3B—H3B120.8
C2A—C3A—H3A120.3C2B—C3B—H3B120.8
C3A—C4A—C5A121.7 (3)C3B—C4B—C5B122.0 (3)
C3A—C4A—N4A119.2 (3)C3B—C4B—N4B119.2 (3)
C5A—C4A—N4A119.1 (3)C5B—C4B—N4B118.8 (3)
C6A—C5A—C4A119.2 (3)C6B—C5B—C4B119.0 (3)
C6A—C5A—H5A120.4C6B—C5B—H5B120.5
C4A—C5A—H5A120.4C4B—C5B—H5B120.5
C5A—C6A—C1A121.4 (3)C5B—C6B—C1B122.2 (3)
C5A—C6A—H6A119.3C5B—C6B—H6B118.9
C1A—C6A—H6A119.3C1B—C6B—H6B118.9
N2A—C7A—C9A115.5 (3)N2B—C7B—C9B115.1 (3)
N2A—C7A—C8A126.2 (3)N2B—C7B—C8B123.7 (3)
C9A—C7A—C8A118.2 (3)C9B—C7B—C8B121.2 (3)
C7A—C8A—H8A109.5C7B—C8B—H8D109.5
C7A—C8A—H8B109.5C7B—C8B—H8E109.5
H8A—C8A—H8B109.5H8D—C8B—H8E109.5
C7A—C8A—H8C109.5C7B—C8B—H8F109.5
H8A—C8A—H8C109.5H8D—C8B—H8F109.5
H8B—C8A—H8C109.5H8E—C8B—H8F109.5
C14A—C9A—C10A119.8 (3)C14B—C9B—C10B119.1 (3)
C14A—C9A—C7A120.5 (3)C14B—C9B—C7B120.9 (3)
C10A—C9A—C7A119.7 (3)C10B—C9B—C7B119.9 (3)
C11A—C10A—C9A119.9 (3)C11B—C10B—C9B120.1 (3)
C11A—C10A—H10A120.0C11B—C10B—H10B120.0
C9A—C10A—H10A120.0C9B—C10B—H10B120.0
O5A—C11A—C10A124.5 (3)O5B—C11B—C10B115.3 (3)
O5A—C11A—C12A115.4 (3)O5B—C11B—C12B123.6 (3)
C10A—C11A—C12A120.2 (4)C10B—C11B—C12B121.0 (3)
C13A—C12A—C11A119.6 (4)C13B—C12B—C11B118.4 (3)
C13A—C12A—H12A120.2C13B—C12B—H12B120.8
C11A—C12A—H12A120.2C11B—C12B—H12B120.8
C12A—C13A—C14A121.0 (4)C12B—C13B—C14B121.1 (4)
C12A—C13A—H13A119.5C12B—C13B—H13B119.4
C14A—C13A—H13A119.5C14B—C13B—H13B119.4
C13A—C14A—C9A119.5 (4)C9B—C14B—C13B120.2 (4)
C13A—C14A—H14A120.2C9B—C14B—H14B119.9
C9A—C14A—H14A120.2C13B—C14B—H14B119.9
O5A—C15A—H15A109.5O5B—C15B—H15D109.5
O5A—C15A—H15B109.5O5B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
O5A—C15A—H15C109.5O5B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C1A—N1A—N2A—C7A172.4 (3)C1B—N1B—N2B—C7B177.2 (3)
N2A—N1A—C1A—C6A1.9 (5)N2B—N1B—C1B—C6B5.4 (5)
N2A—N1A—C1A—C2A179.5 (3)N2B—N1B—C1B—C2B175.2 (3)
N1A—C1A—C2A—C3A179.2 (3)N1B—C1B—C2B—C3B178.8 (3)
C6A—C1A—C2A—C3A0.5 (5)C6B—C1B—C2B—C3B0.7 (5)
N1A—C1A—C2A—N3A2.5 (5)N1B—C1B—C2B—N3B0.9 (5)
C6A—C1A—C2A—N3A176.2 (3)C6B—C1B—C2B—N3B178.5 (3)
O2A—N3A—C2A—C3A2.4 (5)O2B—N3B—C2B—C3B7.3 (5)
O1A—N3A—C2A—C3A176.6 (3)O1B—N3B—C2B—C3B172.1 (3)
O2A—N3A—C2A—C1A179.2 (3)O2B—N3B—C2B—C1B174.7 (3)
O1A—N3A—C2A—C1A0.2 (5)O1B—N3B—C2B—C1B5.9 (5)
C1A—C2A—C3A—C4A0.8 (5)C1B—C2B—C3B—C4B1.2 (5)
N3A—C2A—C3A—C4A177.7 (3)N3B—C2B—C3B—C4B179.1 (3)
C2A—C3A—C4A—C5A1.1 (5)C2B—C3B—C4B—C5B0.3 (5)
C2A—C3A—C4A—N4A178.7 (3)C2B—C3B—C4B—N4B177.7 (3)
O4A—N4A—C4A—C3A177.2 (3)O4B—N4B—C4B—C3B171.9 (3)
O3A—N4A—C4A—C3A3.2 (5)O3B—N4B—C4B—C3B7.7 (5)
O4A—N4A—C4A—C5A5.2 (5)O4B—N4B—C4B—C5B10.6 (5)
O3A—N4A—C4A—C5A174.4 (3)O3B—N4B—C4B—C5B169.8 (3)
C3A—C4A—C5A—C6A0.0 (5)C3B—C4B—C5B—C6B1.1 (5)
N4A—C4A—C5A—C6A177.6 (3)N4B—C4B—C5B—C6B176.3 (3)
C4A—C5A—C6A—C1A1.3 (5)C4B—C5B—C6B—C1B1.7 (5)
N1A—C1A—C6A—C5A179.7 (3)N1B—C1B—C6B—C5B179.8 (3)
C2A—C1A—C6A—C5A1.5 (5)C2B—C1B—C6B—C5B0.8 (5)
N1A—N2A—C7A—C9A179.8 (3)N1B—N2B—C7B—C9B179.9 (3)
N1A—N2A—C7A—C8A1.3 (5)N1B—N2B—C7B—C8B1.7 (5)
N2A—C7A—C9A—C14A180.0 (3)N2B—C7B—C9B—C14B178.8 (3)
C8A—C7A—C9A—C14A1.0 (5)C8B—C7B—C9B—C14B0.5 (5)
N2A—C7A—C9A—C10A0.1 (5)N2B—C7B—C9B—C10B0.6 (5)
C8A—C7A—C9A—C10A179.0 (3)C8B—C7B—C9B—C10B178.9 (3)
C14A—C9A—C10A—C11A1.4 (5)C14B—C9B—C10B—C11B0.0 (5)
C7A—C9A—C10A—C11A178.5 (3)C7B—C9B—C10B—C11B179.4 (3)
C15A—O5A—C11A—C10A2.6 (5)C15B—O5B—C11B—C10B167.7 (3)
C15A—O5A—C11A—C12A178.0 (3)C15B—O5B—C11B—C12B13.8 (5)
C9A—C10A—C11A—O5A179.3 (3)C9B—C10B—C11B—O5B178.6 (3)
C9A—C10A—C11A—C12A0.1 (5)C9B—C10B—C11B—C12B0.0 (5)
O5A—C11A—C12A—C13A179.4 (3)O5B—C11B—C12B—C13B178.2 (3)
C10A—C11A—C12A—C13A1.1 (6)C10B—C11B—C12B—C13B0.3 (5)
C11A—C12A—C13A—C14A1.0 (6)C11B—C12B—C13B—C14B0.6 (5)
C12A—C13A—C14A—C9A0.3 (6)C10B—C9B—C14B—C13B0.2 (5)
C10A—C9A—C14A—C13A1.5 (6)C7B—C9B—C14B—C13B179.2 (3)
C7A—C9A—C14A—C13A178.4 (3)C12B—C13B—C14B—C9B0.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1A0.87 (3)1.94 (4)2.611 (4)133 (3)
N1B—H1NB···O1B0.88 (4)1.96 (3)2.611 (4)130 (4)
C5B—H5B···O3Ai0.932.593.462 (5)156
C6B—H6B···O4Ai0.932.503.277 (4)141
C8A—H8C···O3Bii0.962.573.376 (5)142
C8B—H8E···O4Biii0.962.453.402 (5)170
C12B—H12B···O2Aiv0.932.573.447 (5)157
C13A—H13A···O3Biii0.932.483.204 (5)135
C13B—H13B···O3Aiv0.932.553.448 (5)162
C14B—H14B···O4Biii0.932.473.338 (5)155
C15B—H15E···O3Av0.962.573.301 (5)133
Symmetry codes: (i) x, y, z1; (ii) x+1, y, z+1; (iii) x1, y+1, z; (iv) x1, y+1, z1; (v) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC15H14N4O5
Mr330.30
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.5612 (13), 10.4517 (18), 19.516 (3)
α, β, γ (°)76.034 (4), 89.531 (4), 84.052 (4)
V3)1488.4 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.33 × 0.14 × 0.05
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.964, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
7846, 7846, 5592
Rint0.000
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.296, 1.11
No. of reflections7846
No. of parameters444
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.53, 0.59

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1A0.87 (3)1.94 (4)2.611 (4)133 (3)
N1B—H1NB···O1B0.88 (4)1.96 (3)2.611 (4)130 (4)
C5B—H5B···O3Ai0.932.593.462 (5)156
C6B—H6B···O4Ai0.932.503.277 (4)141
C8A—H8C···O3Bii0.962.573.376 (5)142
C8B—H8E···O4Biii0.962.453.402 (5)170
C12B—H12B···O2Aiv0.932.573.447 (5)157
C13A—H13A···O3Biii0.932.483.204 (5)135
C13B—H13B···O3Aiv0.932.553.448 (5)162
C14B—H14B···O4Biii0.932.473.338 (5)155
C15B—H15E···O3Av0.962.573.301 (5)133
Symmetry codes: (i) x, y, z1; (ii) x+1, y, z+1; (iii) x1, y+1, z; (iv) x1, y+1, z1; (v) x+1, y+1, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

BN and TK thank the Crystal Materials Research Unit, Prince of Songkla University, for financial support. The authors thank Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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