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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Pages o966-o967
doi:10.1107/S1600536809009593

N-[1-(Bi­phenyl-4-yl)ethyl­­idene]-N′-(2,4-di­nitro­phen­yl)hydrazine

Reza Kia,a Hoong-Kun Fun,a* Bijan Etemadib and Hadi Kargarc

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Earth Sciences, College of Sciences, Shiraz University, Shiraz, Iran, and cDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
*Correspondence e-mail: hkfun@usm.my

(Received 13 March 2009; accepted 16 March 2009; online 8 April 2009)

The title compound, C20H16N4O4, contains two crystallographically independent mol­ecules (A and B) in the asymmetric unit. Intra­molecular N—H⋯O hydrogen bonds generate S(6) ring motifs in both molecules. The dihedral angles between the nitro-substituted benzene rings and the two benzene rings in mol­ecules A and B are 14.32 (9), 17.89 (9)° and 13.04 (9) and 25.71 (9)°. The ortho and para nitro groups form dihedral angles of 6.2 (2) and 8.5 (2)° in mol­ecule A, and 5.3 (3) and 13.8 (2)° in mol­ecule B, with the benzene rings to which they are attached. The crystal structure is stabilized by inter­molecular C—H⋯O inter­actions.

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 details of 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 general background and related structures, see: Fun et al. (2009[Fun, H.-K., Kia, R. & Kargar, H. (2009). Acta Cryst. E65, o246-o247.]); Kia et al. (2009[Kia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o382.]); Cordis et al. (1998[Cordis, G. A., Das, D. K. & Riedel, W. (1998). J. Chromatogr. A, 798, 117-123.]); Guillaumont & Nakamura (2000[Guillaumont, D. & Nakamura, S. (2000). Dyes Pigments, 46, 85-92.]); Lamberton et al. (1974[Lamberton, J. A., Nelson, E. R. & Triffett, C. K. (1974). Aust. J. Chem. 27, 1521-1529.]); Niknam et al. (2005[Niknam, K., Kiasat, A. R. & Karimi, S. (2005). Synth. Commun. 35, 2231-2236.]); Raj & Kurup (2006[Raj, B. N. B. & Kurup, M. R. P. (2006). Spectrochim. Acta A, 71, 1251-1260.]); Zegota (1999[Zegota, H. (1999). J. Chromatogr. A, 863, 227-233.]); Zlotorzynska & Lai (1999[Zlotorzynska, E. D. & Lai, E. P. C. (1999). J. Chromatogr. A, 853, 487-796.]); Okabe et al. (1993[Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.]). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C20H16N4O4

  • Mr = 376.37

  • Monoclinic, P 21 /n

  • a = 10.0108 (5) Å

  • b = 14.9422 (8) Å

  • c = 23.3401 (14) Å

  • β = 99.871 (4)°

  • V = 3439.6 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.51 × 0.20 × 0.04 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.949, Tmax = 0.996

  • 38703 measured reflections

  • 10018 independent reflections

  • 6820 reflections with I > 2˘I)

  • Rint = 0.063
Refinement

  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.162

  • S = 1.05

  • 10018 reflections

  • 515 parameters

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

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1NA⋯O1A 0.87 (3) 1.89 (2) 2.596 (2) 137 (2)
N1B—H1NB⋯O1B 0.78 (2) 1.99 (2) 2.600 (2) 134 (2)
C9A—H9AA⋯O2Ai 0.95 2.41 3.084 (2) 127
C3B—H3BA⋯O1Bii 0.95 2.51 3.199 (2) 130
C9B—H9BA⋯O2Bii 0.95 2.39 3.174 (3) 139
C17A—H17A⋯O3Aiii 0.95 2.59 3.498 (3) 161
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x+{\script{3\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009593/at2742sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009593/at2742Isup2.hkl

checkCIF report


Comment top

2,4-Dinitrophenylhydrazones play a more important role as stabilizers for the detection, characterization and protection of the carbonyl groups than phenylhydrazones (Niknam et al., 2005). 2,4-Dinitrophenylhydrazone derivatives are widely used in various forms of analytical chemistry (Lamberton et al., 1974; Zegota, 1999; Cordis et al., 1998; Zlotorzynska & Lai, 1999) and are also used as dyes (Guillaumont & Nakamura, 2000). They are also found to have versatile coordinating abilities towards different metal ions (Raj & Kurup, 2006). In addition, some phenylhydrazone derivatives have been shown to be potentially DNA-damaging and mutagenic agents (Okabe et al., 1993). For these reasons, the structure of the title compound was reported here.

The bond lengths (Allen et al., 1987) and angles in the title compound (Fig. 1) have normal values and are comparable to the related structures (Fun et al. 2009; Kia et al. 2009). Intramolecular N—H···O hydrogen bonds generate S(6) ring motifs (Bernstein et al.,1995). The dihedral angle between the two benzene rings and the nitro-substituted benzene rings in molecules A and B are 14.32 (9), 17.89 (9), 13.04 (9), and 25.71 (9)°, respectively. The ortho and para-substituted nitro groups form dihedral angles of 6.2 (2), 8.5 (2)° in molecule A and 5.3 (3) and 13.8 (2)° in molecule B, to the benzene rings to which they are attached. The crystal structure is further stabilized by intermolecular C—H···O interactions (Table 1 and Fig.2 ).

Related literature top

For bond length data, see: Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For related literature, see: Fun et al. (2009); Kia et al. (2009); Cordis et al. (1998); Guillaumont & Nakamura (2000); Lamberton et al. (1974); Niknam et al. (2005); Raj & Kurup (2006); Zegota (1999); Zlotorzynska & Lai (1999); Okabe et al. (1993). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986). It would be much more useful to readers if, instead of just "For related literature, see···" it said, for example, "For general background, see··· For related structures, see···; etc. Please revise this section as indicated.

Experimental top

The title compound was synthesized based on the reported procedure (Okabe et al. 1993) except that p-phenyl-acetophenone (1 mmol) was used instead. Single crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a saturated solution of the resulted compound in acetone.

Refinement top

N-bound H atom was located from the difference Fourier map and refined freely; see, Table 1. The remaining H atoms were positioned geometrically and constrained with a riding model approximation with C—H = 0.95–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 50% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the c-axis, showing linking of molecules into dimers through intermolecular C—H···O interactions. Intermolecular interactions are shown as dashed lines.
N-[1-(Biphenyl-4-yl)ethylidene]-N'-(2,4-dinitrophenyl)hydrazine top
Crystal data top
C20H16N4O4F(000) = 1568
Mr = 376.37Dx = 1.454 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5139 reflections
a = 10.0108 (5) Åθ = 2.5–28.5°
b = 14.9422 (8) ŵ = 0.10 mm−1
c = 23.3401 (14) ÅT = 100 K
β = 99.871 (4)°Plate, red
V = 3439.6 (3) Å30.51 × 0.20 × 0.04 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		10018 independent reflections
Radiation source: fine-focus sealed tube6820 reflections with I > 2˘I)
Graphite monochromatorRint = 0.063
ϕ and ω scansθmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −14→14
Tmin = 0.949, Tmax = 0.996k = −17→21
38703 measured reflectionsl = −24→32
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0656P)2 + 1.1266P]
where P = (Fo2 + 2Fc2)/3
10018 reflections(Δ/σ)max < 0.001
515 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C20H16N4O4V = 3439.6 (3) Å3
Mr = 376.37Z = 8
Monoclinic, P21/nMo Kα radiation
a = 10.0108 (5) ŵ = 0.10 mm−1
b = 14.9422 (8) ÅT = 100 K
c = 23.3401 (14) Å0.51 × 0.20 × 0.04 mm
β = 99.871 (4)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		10018 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		6820 reflections with I > 2˘I)
Tmin = 0.949, Tmax = 0.996Rint = 0.063
38703 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.35 e Å−3
10018 reflectionsΔρmin = −0.32 e Å−3
515 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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
O1A0.76069 (14)0.22620 (9)0.23590 (6)0.0246 (3)
O2A0.58648 (18)0.23537 (10)0.16763 (8)0.0485 (5)
O3A0.32139 (14)−0.01433 (9)0.09644 (7)0.0278 (3)
O4A0.37325 (14)−0.14680 (9)0.13206 (7)0.0280 (3)
N1A0.86347 (15)0.07099 (11)0.26819 (7)0.0172 (3)
H1NA0.866 (2)0.1289 (17)0.2702 (11)0.039 (7)*
N2A0.94751 (15)0.01368 (10)0.30306 (7)0.0171 (3)
N3A0.66711 (17)0.19105 (10)0.20141 (8)0.0243 (4)
N4A0.39718 (16)−0.06641 (11)0.12752 (7)0.0209 (3)
C1A0.75102 (18)0.03800 (12)0.23386 (8)0.0163 (4)
C2A0.72659 (18)−0.05521 (12)0.22963 (8)0.0185 (4)
H2AA0.7896−0.09510.25150.022*
C3A0.61413 (19)−0.08917 (12)0.19472 (8)0.0196 (4)
H3AA0.5996−0.15200.19240.024*
C4A0.52048 (18)−0.03081 (12)0.16247 (8)0.0189 (4)
C5A0.53958 (18)0.06021 (12)0.16430 (8)0.0195 (4)
H5AA0.47640.09900.14150.023*
C6A0.65363 (18)0.09453 (12)0.20027 (9)0.0187 (4)
C7A1.05071 (18)0.04897 (12)0.33658 (8)0.0172 (4)
C8A1.13686 (18)−0.01546 (12)0.37413 (8)0.0173 (4)
C9A1.08960 (19)−0.10274 (12)0.37967 (8)0.0200 (4)
H9AA1.0000−0.11790.36170.024*
C10A1.17056 (19)−0.16714 (12)0.41074 (9)0.0203 (4)
H10A1.1364−0.22610.41320.024*
C11A1.30261 (18)−0.14688 (12)0.43877 (8)0.0180 (4)
C12A1.34820 (19)−0.05927 (12)0.43486 (8)0.0196 (4)
H12A1.4364−0.04360.45420.024*
C13A1.26710 (18)0.00583 (12)0.40313 (8)0.0186 (4)
H13A1.30060.06500.40120.022*
C14A1.38924 (18)−0.21713 (12)0.47113 (8)0.0194 (4)
C15A1.3764 (2)−0.30658 (13)0.45349 (9)0.0234 (4)
H15A1.3121−0.32240.42020.028*
C16A1.4563 (2)−0.37248 (14)0.48411 (10)0.0277 (5)
H16A1.4457−0.43300.47180.033*
C17A1.5511 (2)−0.35083 (14)0.53224 (10)0.0287 (5)
H17A1.6069−0.39600.55250.034*
C18A1.5644 (2)−0.26259 (14)0.55081 (10)0.0297 (5)
H18A1.6286−0.24740.58430.036*
C19A1.4841 (2)−0.19649 (14)0.52056 (9)0.0246 (4)
H19A1.4938−0.13630.53360.029*
C20A1.08413 (19)0.14713 (12)0.33820 (9)0.0214 (4)
H20A1.00610.18140.34640.032*
H20B1.10550.16560.30050.032*
H20C1.16250.15840.36870.032*
O1B0.24703 (15)0.26357 (9)0.23255 (7)0.0323 (4)
O2B0.4466 (2)0.24962 (11)0.28413 (10)0.0599 (6)
O3B0.66656 (15)0.48817 (10)0.39824 (7)0.0307 (3)
O4B0.60838 (14)0.62418 (9)0.37192 (6)0.0278 (3)
N1B0.13039 (16)0.41932 (11)0.21771 (8)0.0203 (4)
H1NB0.126 (2)0.3682 (15)0.2101 (10)0.025 (6)*
N2B0.03856 (15)0.48109 (10)0.19137 (7)0.0189 (3)
N3B0.34763 (19)0.29565 (11)0.26485 (9)0.0306 (4)
N4B0.58899 (16)0.54278 (11)0.37022 (7)0.0230 (4)
C1B0.24162 (18)0.44779 (12)0.25439 (8)0.0184 (4)
C2B0.25660 (19)0.53943 (12)0.27013 (9)0.0200 (4)
H2BA0.18800.58080.25430.024*
C3B0.36773 (19)0.56955 (13)0.30758 (9)0.0210 (4)
H3BA0.37630.63130.31710.025*
C4B0.46877 (19)0.50923 (12)0.33182 (8)0.0198 (4)
C5B0.46021 (19)0.41996 (13)0.31842 (9)0.0215 (4)
H5BA0.52930.37970.33540.026*
C6B0.34862 (19)0.38920 (12)0.27952 (9)0.0206 (4)
C7B−0.06623 (19)0.45005 (12)0.15687 (8)0.0190 (4)
C8B−0.15944 (18)0.51924 (12)0.12712 (8)0.0186 (4)
C9B−0.14824 (19)0.60798 (12)0.14622 (8)0.0191 (4)
H9BA−0.08120.62350.17860.023*
C10B−0.23311 (18)0.67353 (12)0.11872 (8)0.0191 (4)
H10B−0.22420.73320.13300.023*
C11B−0.33207 (18)0.65396 (12)0.07024 (9)0.0190 (4)
C12B−0.34157 (19)0.56507 (13)0.05072 (9)0.0214 (4)
H12B−0.40660.54980.01750.026*
C13B−0.25785 (19)0.49892 (13)0.07897 (9)0.0207 (4)
H13B−0.26770.43900.06530.025*
C14B−0.42078 (19)0.72507 (13)0.03980 (8)0.0198 (4)
C15B−0.3711 (2)0.81216 (13)0.03623 (9)0.0228 (4)
H15B−0.28140.82630.05470.027*
C16B−0.4522 (2)0.87809 (14)0.00587 (9)0.0272 (5)
H16B−0.41730.93680.00330.033*
C17B−0.5834 (2)0.85851 (14)−0.02069 (9)0.0289 (5)
H17B−0.63810.9037−0.04160.035*
C18B−0.6353 (2)0.77304 (14)−0.01678 (9)0.0280 (5)
H18B−0.72580.7598−0.03450.034*
C19B−0.5540 (2)0.70702 (14)0.01314 (9)0.0235 (4)
H19B−0.58970.64850.01550.028*
C20B−0.0951 (2)0.35244 (12)0.14521 (9)0.0233 (4)
H20D−0.06880.31840.18130.035*
H20E−0.04320.33110.11590.035*
H20F−0.19220.34410.13080.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0273 (7)0.0135 (7)0.0311 (8)−0.0023 (5)−0.0008 (6)−0.0008 (6)
O2A0.0494 (10)0.0149 (8)0.0677 (13)0.0038 (7)−0.0279 (9)0.0072 (8)
O3A0.0255 (7)0.0247 (8)0.0305 (8)0.0004 (6)−0.0033 (6)0.0005 (6)
O4A0.0298 (8)0.0167 (7)0.0364 (9)−0.0058 (6)0.0028 (7)−0.0039 (6)
N1A0.0191 (8)0.0100 (7)0.0219 (9)0.0013 (6)0.0019 (6)0.0020 (6)
N2A0.0189 (7)0.0132 (7)0.0193 (8)0.0021 (6)0.0034 (6)0.0031 (6)
N3A0.0276 (9)0.0115 (8)0.0315 (10)0.0014 (6)−0.0011 (7)0.0008 (7)
N4A0.0216 (8)0.0182 (8)0.0229 (9)−0.0009 (6)0.0037 (7)−0.0037 (7)
C1A0.0184 (8)0.0126 (8)0.0189 (10)0.0008 (7)0.0061 (7)0.0008 (7)
C2A0.0210 (9)0.0137 (9)0.0208 (10)0.0009 (7)0.0040 (7)0.0017 (7)
C3A0.0233 (9)0.0115 (9)0.0246 (10)−0.0007 (7)0.0056 (8)0.0000 (7)
C4A0.0194 (9)0.0171 (9)0.0203 (10)−0.0012 (7)0.0039 (7)−0.0011 (7)
C5A0.0193 (9)0.0159 (9)0.0230 (10)0.0022 (7)0.0033 (7)0.0014 (8)
C6A0.0198 (9)0.0113 (8)0.0250 (10)0.0007 (7)0.0041 (7)0.0013 (7)
C7A0.0193 (9)0.0141 (9)0.0190 (10)−0.0009 (7)0.0052 (7)−0.0006 (7)
C8A0.0198 (9)0.0130 (9)0.0195 (10)0.0009 (7)0.0044 (7)−0.0007 (7)
C9A0.0198 (9)0.0149 (9)0.0239 (10)−0.0021 (7)−0.0002 (7)−0.0021 (8)
C10A0.0232 (9)0.0129 (9)0.0242 (10)−0.0005 (7)0.0025 (8)0.0016 (8)
C11A0.0199 (9)0.0163 (9)0.0182 (10)0.0013 (7)0.0046 (7)−0.0006 (7)
C12A0.0182 (9)0.0180 (9)0.0224 (10)−0.0012 (7)0.0029 (7)−0.0011 (8)
C13A0.0209 (9)0.0135 (9)0.0216 (10)−0.0020 (7)0.0047 (7)−0.0002 (7)
C14A0.0181 (9)0.0201 (10)0.0209 (10)0.0023 (7)0.0058 (7)0.0050 (8)
C15A0.0267 (10)0.0196 (10)0.0242 (11)0.0022 (8)0.0051 (8)0.0012 (8)
C16A0.0327 (11)0.0197 (10)0.0323 (12)0.0071 (8)0.0097 (9)0.0043 (9)
C17A0.0229 (10)0.0283 (11)0.0355 (13)0.0079 (8)0.0065 (9)0.0127 (10)
C18A0.0247 (10)0.0322 (12)0.0301 (12)−0.0008 (9)−0.0011 (9)0.0059 (10)
C19A0.0228 (10)0.0215 (10)0.0283 (11)0.0005 (8)0.0011 (8)0.0042 (8)
C20A0.0232 (9)0.0127 (9)0.0267 (11)−0.0019 (7)−0.0007 (8)0.0003 (8)
O1B0.0347 (8)0.0152 (7)0.0431 (10)−0.0039 (6)−0.0040 (7)0.0001 (7)
O2B0.0561 (12)0.0208 (9)0.0871 (16)0.0157 (8)−0.0319 (11)−0.0047 (9)
O3B0.0257 (7)0.0305 (8)0.0330 (9)0.0016 (6)−0.0027 (6)0.0051 (7)
O4B0.0290 (8)0.0211 (8)0.0334 (9)−0.0027 (6)0.0059 (6)−0.0048 (6)
N1B0.0223 (8)0.0094 (8)0.0286 (10)−0.0005 (6)0.0030 (7)0.0023 (7)
N2B0.0194 (8)0.0153 (8)0.0223 (9)0.0014 (6)0.0046 (6)0.0033 (6)
N3B0.0334 (10)0.0144 (8)0.0405 (11)0.0011 (7)−0.0033 (8)0.0031 (8)
N4B0.0213 (8)0.0236 (9)0.0253 (9)0.0000 (7)0.0075 (7)−0.0006 (7)
C1B0.0199 (9)0.0156 (9)0.0209 (10)−0.0009 (7)0.0070 (7)0.0024 (7)
C2B0.0215 (9)0.0149 (9)0.0247 (10)0.0012 (7)0.0068 (8)0.0020 (8)
C3B0.0239 (9)0.0153 (9)0.0251 (11)0.0002 (7)0.0079 (8)0.0013 (8)
C4B0.0212 (9)0.0182 (9)0.0206 (10)−0.0019 (7)0.0054 (7)0.0018 (8)
C5B0.0197 (9)0.0216 (10)0.0233 (10)0.0017 (7)0.0039 (8)0.0049 (8)
C6B0.0238 (10)0.0121 (9)0.0264 (11)0.0005 (7)0.0057 (8)0.0033 (8)
C7B0.0217 (9)0.0162 (9)0.0209 (10)−0.0010 (7)0.0083 (8)0.0012 (8)
C8B0.0179 (9)0.0171 (9)0.0214 (10)−0.0006 (7)0.0052 (7)0.0017 (8)
C9B0.0200 (9)0.0163 (9)0.0209 (10)−0.0030 (7)0.0032 (7)0.0002 (8)
C10B0.0211 (9)0.0145 (9)0.0220 (10)−0.0010 (7)0.0043 (8)−0.0017 (7)
C11B0.0184 (9)0.0181 (9)0.0216 (10)0.0000 (7)0.0065 (7)0.0023 (8)
C12B0.0197 (9)0.0205 (10)0.0230 (10)−0.0030 (7)0.0005 (8)0.0000 (8)
C13B0.0227 (9)0.0150 (9)0.0242 (10)−0.0043 (7)0.0041 (8)−0.0028 (8)
C14B0.0216 (9)0.0203 (10)0.0180 (10)0.0015 (7)0.0051 (7)−0.0008 (8)
C15B0.0251 (10)0.0204 (10)0.0230 (11)0.0011 (7)0.0044 (8)−0.0012 (8)
C16B0.0353 (12)0.0180 (10)0.0292 (12)0.0034 (8)0.0079 (9)0.0016 (9)
C17B0.0329 (11)0.0279 (11)0.0248 (11)0.0114 (9)0.0021 (9)0.0019 (9)
C18B0.0238 (10)0.0335 (12)0.0259 (11)0.0043 (8)0.0018 (8)−0.0033 (9)
C19B0.0243 (10)0.0237 (10)0.0228 (10)0.0000 (8)0.0045 (8)−0.0014 (8)
C20B0.0255 (10)0.0137 (9)0.0310 (11)−0.0029 (7)0.0053 (8)0.0009 (8)
Geometric parameters (Å, º) top
O1A—N3A1.242 (2)O1B—N3B1.246 (2)
O2A—N3A1.222 (2)O2B—N3B1.226 (2)
O3A—N4A1.232 (2)O3B—N4B1.234 (2)
O4A—N4A1.233 (2)O4B—N4B1.231 (2)
N1A—C1A1.358 (2)N1B—C1B1.352 (2)
N1A—N2A1.367 (2)N1B—N2B1.372 (2)
N1A—H1NA0.87 (2)N1B—H1NB0.78 (2)
N2A—C7A1.296 (2)N2B—C7B1.294 (2)
N3A—C6A1.448 (2)N3B—C6B1.439 (2)
N4A—C4A1.458 (2)N4B—C4B1.461 (3)
C1A—C2A1.415 (2)C1B—C2B1.419 (3)
C1A—C6A1.420 (2)C1B—C6B1.429 (3)
C2A—C3A1.369 (3)C2B—C3B1.368 (3)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.401 (3)C3B—C4B1.400 (3)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.373 (3)C4B—C5B1.369 (3)
C5A—C6A1.394 (3)C5B—C6B1.391 (3)
C5A—H5AA0.9500C5B—H5BA0.9500
C7A—C8A1.476 (3)C7B—C8B1.483 (3)
C7A—C20A1.504 (2)C7B—C20B1.503 (3)
C8A—C13A1.399 (3)C8B—C13B1.395 (3)
C8A—C9A1.401 (2)C8B—C9B1.397 (3)
C9A—C10A1.381 (3)C9B—C10B1.381 (3)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.404 (3)C10B—C11B1.401 (3)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.394 (3)C11B—C12B1.402 (3)
C11A—C14A1.483 (3)C11B—C14B1.485 (3)
C12A—C13A1.395 (3)C12B—C13B1.387 (3)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
C14A—C19A1.397 (3)C14B—C19B1.398 (3)
C14A—C15A1.398 (3)C14B—C15B1.401 (3)
C15A—C16A1.387 (3)C15B—C16B1.391 (3)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.379 (3)C16B—C17B1.385 (3)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.387 (3)C17B—C18B1.387 (3)
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.388 (3)C18B—C19B1.388 (3)
C18A—H18A0.9500C18B—H18B0.9500
C19A—H19A0.9500C19B—H19B0.9500
C20A—H20A0.9800C20B—H20D0.9800
C20A—H20B0.9800C20B—H20E0.9800
C20A—H20C0.9800C20B—H20F0.9800
C1A—N1A—N2A119.17 (15)C1B—N1B—N2B119.21 (16)
C1A—N1A—H1NA114.3 (17)C1B—N1B—H1NB117.1 (17)
N2A—N1A—H1NA125.6 (17)N2B—N1B—H1NB123.4 (17)
C7A—N2A—N1A116.74 (15)C7B—N2B—N1B116.56 (16)
O2A—N3A—O1A122.02 (16)O2B—N3B—O1B121.65 (18)
O2A—N3A—C6A118.59 (17)O2B—N3B—C6B119.03 (18)
O1A—N3A—C6A119.38 (16)O1B—N3B—C6B119.32 (17)
O3A—N4A—O4A123.82 (16)O4B—N4B—O3B123.70 (17)
O3A—N4A—C4A118.40 (15)O4B—N4B—C4B117.88 (16)
O4A—N4A—C4A117.75 (16)O3B—N4B—C4B118.41 (16)
N1A—C1A—C2A120.97 (17)N1B—C1B—C2B120.45 (17)
N1A—C1A—C6A122.09 (16)N1B—C1B—C6B123.04 (17)
C2A—C1A—C6A116.93 (17)C2B—C1B—C6B116.52 (17)
C3A—C2A—C1A121.40 (17)C3B—C2B—C1B121.41 (18)
C3A—C2A—H2AA119.3C3B—C2B—H2BA119.3
C1A—C2A—H2AA119.3C1B—C2B—H2BA119.3
C2A—C3A—C4A119.68 (17)C2B—C3B—C4B119.92 (18)
C2A—C3A—H3AA120.2C2B—C3B—H3BA120.0
C4A—C3A—H3AA120.2C4B—C3B—H3BA120.0
C5A—C4A—C3A121.53 (18)C5B—C4B—C3B121.48 (18)
C5A—C4A—N4A118.60 (17)C5B—C4B—N4B119.16 (17)
C3A—C4A—N4A119.84 (16)C3B—C4B—N4B119.30 (17)
C4A—C5A—C6A118.58 (17)C4B—C5B—C6B118.86 (18)
C4A—C5A—H5AA120.7C4B—C5B—H5BA120.6
C6A—C5A—H5AA120.7C6B—C5B—H5BA120.6
C5A—C6A—C1A121.85 (16)C5B—C6B—C1B121.79 (17)
C5A—C6A—N3A116.20 (16)C5B—C6B—N3B116.63 (17)
C1A—C6A—N3A121.94 (16)C1B—C6B—N3B121.56 (18)
N2A—C7A—C8A114.65 (16)N2B—C7B—C8B114.79 (16)
N2A—C7A—C20A124.26 (17)N2B—C7B—C20B124.82 (18)
C8A—C7A—C20A121.09 (16)C8B—C7B—C20B120.38 (17)
C13A—C8A—C9A117.93 (17)C13B—C8B—C9B118.07 (17)
C13A—C8A—C7A122.70 (16)C13B—C8B—C7B121.75 (17)
C9A—C8A—C7A119.32 (16)C9B—C8B—C7B120.16 (17)
C10A—C9A—C8A121.34 (18)C10B—C9B—C8B121.04 (18)
C10A—C9A—H9AA119.3C10B—C9B—H9BA119.5
C8A—C9A—H9AA119.3C8B—C9B—H9BA119.5
C9A—C10A—C11A121.02 (17)C9B—C10B—C11B121.39 (17)
C9A—C10A—H10A119.5C9B—C10B—H10B119.3
C11A—C10A—H10A119.5C11B—C10B—H10B119.3
C12A—C11A—C10A117.69 (17)C10B—C11B—C12B117.35 (17)
C12A—C11A—C14A121.89 (17)C10B—C11B—C14B121.27 (17)
C10A—C11A—C14A120.42 (16)C12B—C11B—C14B121.37 (18)
C11A—C12A—C13A121.46 (17)C13B—C12B—C11B121.24 (18)
C11A—C12A—H12A119.3C13B—C12B—H12B119.4
C13A—C12A—H12A119.3C11B—C12B—H12B119.4
C12A—C13A—C8A120.50 (17)C12B—C13B—C8B120.90 (18)
C12A—C13A—H13A119.8C12B—C13B—H13B119.6
C8A—C13A—H13A119.8C8B—C13B—H13B119.6
C19A—C14A—C15A118.00 (18)C19B—C14B—C15B118.31 (18)
C19A—C14A—C11A121.30 (17)C19B—C14B—C11B121.43 (17)
C15A—C14A—C11A120.69 (18)C15B—C14B—C11B120.25 (17)
C16A—C15A—C14A120.7 (2)C16B—C15B—C14B120.41 (19)
C16A—C15A—H15A119.6C16B—C15B—H15B119.8
C14A—C15A—H15A119.6C14B—C15B—H15B119.8
C17A—C16A—C15A120.6 (2)C17B—C16B—C15B120.31 (19)
C17A—C16A—H16A119.7C17B—C16B—H16B119.8
C15A—C16A—H16A119.7C15B—C16B—H16B119.8
C16A—C17A—C18A119.57 (19)C16B—C17B—C18B120.1 (2)
C16A—C17A—H17A120.2C16B—C17B—H17B119.9
C18A—C17A—H17A120.2C18B—C17B—H17B119.9
C17A—C18A—C19A120.1 (2)C17B—C18B—C19B119.6 (2)
C17A—C18A—H18A120.0C17B—C18B—H18B120.2
C19A—C18A—H18A120.0C19B—C18B—H18B120.2
C18A—C19A—C14A121.0 (2)C18B—C19B—C14B121.25 (19)
C18A—C19A—H19A119.5C18B—C19B—H19B119.4
C14A—C19A—H19A119.5C14B—C19B—H19B119.4
C7A—C20A—H20A109.5C7B—C20B—H20D109.5
C7A—C20A—H20B109.5C7B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
C7A—C20A—H20C109.5C7B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
C1A—N1A—N2A—C7A−177.50 (16)C1B—N1B—N2B—C7B−179.75 (16)
N2A—N1A—C1A—C2A−6.0 (2)N2B—N1B—C1B—C2B6.4 (3)
N2A—N1A—C1A—C6A174.68 (16)N2B—N1B—C1B—C6B−174.03 (17)
N1A—C1A—C2A—C3A−179.39 (17)N1B—C1B—C2B—C3B179.40 (17)
C6A—C1A—C2A—C3A0.0 (3)C6B—C1B—C2B—C3B−0.2 (3)
C1A—C2A—C3A—C4A−0.2 (3)C1B—C2B—C3B—C4B−0.8 (3)
C2A—C3A—C4A—C5A1.0 (3)C2B—C3B—C4B—C5B0.8 (3)
C2A—C3A—C4A—N4A−176.91 (16)C2B—C3B—C4B—N4B177.97 (16)
O3A—N4A—C4A—C5A7.1 (3)O4B—N4B—C4B—C5B164.84 (17)
O4A—N4A—C4A—C5A−171.05 (17)O3B—N4B—C4B—C5B−13.8 (3)
O3A—N4A—C4A—C3A−174.96 (17)O4B—N4B—C4B—C3B−12.4 (2)
O4A—N4A—C4A—C3A6.9 (3)O3B—N4B—C4B—C3B168.92 (17)
C3A—C4A—C5A—C6A−1.5 (3)C3B—C4B—C5B—C6B0.4 (3)
N4A—C4A—C5A—C6A176.43 (16)N4B—C4B—C5B—C6B−176.81 (16)
C4A—C5A—C6A—C1A1.3 (3)C4B—C5B—C6B—C1B−1.5 (3)
C4A—C5A—C6A—N3A−178.73 (17)C4B—C5B—C6B—N3B177.20 (17)
N1A—C1A—C6A—C5A178.84 (17)N1B—C1B—C6B—C5B−178.20 (18)
C2A—C1A—C6A—C5A−0.5 (3)C2B—C1B—C6B—C5B1.4 (3)
N1A—C1A—C6A—N3A−1.2 (3)N1B—C1B—C6B—N3B3.2 (3)
C2A—C1A—C6A—N3A179.46 (16)C2B—C1B—C6B—N3B−177.22 (17)
O2A—N3A—C6A—C5A−6.5 (3)O2B—N3B—C6B—C5B−4.2 (3)
O1A—N3A—C6A—C5A174.46 (17)O1B—N3B—C6B—C5B176.37 (18)
O2A—N3A—C6A—C1A173.51 (19)O2B—N3B—C6B—C1B174.5 (2)
O1A—N3A—C6A—C1A−5.5 (3)O1B—N3B—C6B—C1B−4.9 (3)
N1A—N2A—C7A—C8A178.93 (15)N1B—N2B—C7B—C8B−177.16 (15)
N1A—N2A—C7A—C20A−1.4 (3)N1B—N2B—C7B—C20B1.7 (3)
N2A—C7A—C8A—C13A165.23 (17)N2B—C7B—C8B—C13B164.50 (17)
C20A—C7A—C8A—C13A−14.4 (3)C20B—C7B—C8B—C13B−14.4 (3)
N2A—C7A—C8A—C9A−12.4 (2)N2B—C7B—C8B—C9B−14.0 (2)
C20A—C7A—C8A—C9A167.97 (17)C20B—C7B—C8B—C9B167.14 (17)
C13A—C8A—C9A—C10A−2.7 (3)C13B—C8B—C9B—C10B0.8 (3)
C7A—C8A—C9A—C10A175.07 (17)C7B—C8B—C9B—C10B179.31 (17)
C8A—C9A—C10A—C11A1.1 (3)C8B—C9B—C10B—C11B−1.0 (3)
C9A—C10A—C11A—C12A1.0 (3)C9B—C10B—C11B—C12B0.0 (3)
C9A—C10A—C11A—C14A−178.94 (17)C9B—C10B—C11B—C14B−178.35 (17)
C10A—C11A—C12A—C13A−1.5 (3)C10B—C11B—C12B—C13B1.1 (3)
C14A—C11A—C12A—C13A178.42 (17)C14B—C11B—C12B—C13B179.48 (17)
C11A—C12A—C13A—C8A−0.1 (3)C11B—C12B—C13B—C8B−1.3 (3)
C9A—C8A—C13A—C12A2.1 (3)C9B—C8B—C13B—C12B0.4 (3)
C7A—C8A—C13A—C12A−175.51 (17)C7B—C8B—C13B—C12B−178.16 (17)
C12A—C11A—C14A—C19A32.5 (3)C10B—C11B—C14B—C19B−147.87 (18)
C10A—C11A—C14A—C19A−147.56 (19)C12B—C11B—C14B—C19B33.8 (3)
C12A—C11A—C14A—C15A−148.62 (18)C10B—C11B—C14B—C15B33.4 (3)
C10A—C11A—C14A—C15A31.3 (3)C12B—C11B—C14B—C15B−144.91 (18)
C19A—C14A—C15A—C16A−0.4 (3)C19B—C14B—C15B—C16B−1.2 (3)
C11A—C14A—C15A—C16A−179.29 (17)C11B—C14B—C15B—C16B177.55 (18)
C14A—C15A—C16A—C17A−0.7 (3)C14B—C15B—C16B—C17B0.6 (3)
C15A—C16A—C17A—C18A1.3 (3)C15B—C16B—C17B—C18B0.5 (3)
C16A—C17A—C18A—C19A−0.9 (3)C16B—C17B—C18B—C19B−1.0 (3)
C17A—C18A—C19A—C14A−0.1 (3)C17B—C18B—C19B—C14B0.4 (3)
C15A—C14A—C19A—C18A0.8 (3)C15B—C14B—C19B—C18B0.7 (3)
C11A—C14A—C19A—C18A179.68 (18)C11B—C14B—C19B—C18B−178.02 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1A0.87 (3)1.89 (2)2.596 (2)137 (2)
N1B—H1NB···O1B0.78 (2)1.99 (2)2.600 (2)134 (2)
C9A—H9AA···O2Ai0.952.413.084 (2)127
C3B—H3BA···O1Bii0.952.513.199 (2)130
C9B—H9BA···O2Bii0.952.393.174 (3)139
C17A—H17A···O3Aiii0.952.593.498 (3)161
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+3/2, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H16N4O4
Mr376.37
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)10.0108 (5), 14.9422 (8), 23.3401 (14)
β (°) 99.871 (4)
V (Å3)3439.6 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.51 × 0.20 × 0.04
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.949, 0.996
No. of measured, independent and
observed [I > 2˘I)] reflections		38703, 10018, 6820
Rint0.063
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.162, 1.05
No. of reflections10018
No. of parameters515
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.35, −0.32

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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)1.89 (2)2.596 (2)137 (2)
N1B—H1NB···O1B0.78 (2)1.99 (2)2.600 (2)134 (2)
C9A—H9AA···O2Ai0.952.41003.084 (2)127
C3B—H3BA···O1Bii0.952.51003.199 (2)130
C9B—H9BA···O2Bii0.952.39003.174 (3)139
C17A—H17A···O3Aiii0.952.59003.498 (3)161
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+3/2, −y−1/2, z+1/2.
 

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a postdoctoral research fellowship. BE thanks Shiraz University for financial support. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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ISSN: 2056-9890
Volume 65| Part 5| May 2009| Pages o966-o967
doi:10.1107/S1600536809009593
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