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Acta Cryst. (2009). E65, o966-o967    [ doi:10.1107/S1600536809009593 ]

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

R. Kia, H.-K. Fun, B. Etemadi and H. Kargar

Abstract top

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.

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)
graphiteRint = 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 reflectionsθmax = 30.0°
Refinement top
R[F2 > 2σ(F2)] = 0.070H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162Δρmax = 0.35 e Å−3
S = 1.05Δρmin = −0.32 e Å−3
10018 reflectionsAbsolute structure: ?
515 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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, °) 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, °) 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.
Table 1
Hydrogen-bond geometry (Å, °) 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.
Acknowledgements top

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.

references
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