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Acta Cryst. (2008). E64, o1907-o1908    [ doi:10.1107/S1600536808028328 ]

N'-[(Z)-4-(Dimethylamino)benzylidene]-4-nitrobenzohydrazide monohydrate

H.-K. Fun, S. R. Jebas, K. V. Sujith, P. S. Patil and B. Kalluraya

Abstract top

In the asymmetric unit of the title compound, C16H16N4O3·H2O, there are two symmetry-independent hydrazide molecules with almost identical geometries, and two independent water molecules. The dihedral angles between the two benzene rings in the two hydrazide molecules are 0.11 (5) and 0.77 (5)°. In one molecule, an intramolecular C-H...O hydrogen bond generates a ring of graph-set motif S(5). Intermolecular N-H...O, O-H...O, O-H...N and C-H...O hydrogen bonds and [pi]-[pi] stacking interactions between the benzene rings [centroid-centroid distances in the range 3.5021 (6)-3.6403 (6) Å] are observed, together with O...O [2.7226 (11) Å], O...N [2.7072 (10) Å] and N...O [2.7072 (10)-2.8582 (12) Å] short contacts. The hydrazine molecules are stacked along the b axis and adjacent molecules are linked by water molecules.

Comment top

Hydrazones possessing an azometine —NHN═CH— proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. These observations have been the guides for the development of new hydrazones. Hydrazones containing an azometine —NHN═CH— proton are synthesized by heating the appropriate substituted hydrazines/hydrazides with aldehydes and ketones in solvents like ethanol, methanol, tetrahydrofuran, butanol, glacial acetic acid, ethanol-glacial acetic acid. Another synthetic route for the synthesis of hydrazones is the coupling of aryldiazonium salts with active hydrogen compounds (Rollas & Küçükgüzel, 2007). Hydrazide-hydrazones compounds are not only intermediates but they are also very effective organic compounds in their own right. When they are used as intermediates, coupling products can be synthesized by using the active hydrogen component of the —CONHN═CH— azometine group (Singh et al., 1992). N-Alkyl hydrazides can be synthesized by reduction of hydrazones with NaBH4 (Ergenç & Günay, 1998), substituted 1,3,4-oxadiazolines can be synthesized when hydrazones are heated in the presence of acetic anhydride (Durgun et al., 1993). Prompted by these review and in continuation of our work (Fun et al., 2008), we herein report the crystal structure of the title compound, (I).

There are two independent molecules (A and B) in the asymmetric unit of (I), with similar geometries (Fig. 1.) The bond lengths and angles are found to have normal values (Allen et al., 1987). The dihedral angle formed by the benzene (C1A–C6A) and (C9A–C14A) rings is 0.11 (5)° in molecule A and that between the benzene (C1B–C6B) and (C9B–C14B) rings is 0.77 (5)° in molecule B, indicating that they are coplanar. In molecule B, an intramolecular C—H···O hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995).

The crystal packing is consolidated by N—H···O, O—H···O, O—H···N and C—H···O inter and intramolecular hydrogen bonding (Table 1). Furthermore, the packing is strengthened by π–π stacking interactions involving the benzene (C1A–C6A) (Cg1) and the symmetry related (C9B–C14B) ring (Cg4) [Cg1···Cg4i = 3.5021 Å; Cg1—Cg4ii = 3.6403 (6) Å; symmetry codes: (i) 2-x, 1-y, 1-z; (ii) 2-x, -y, 1-z] and the benzene (C9A–C14A) ring (Cg2) and the symmetry related (C9B–C14B) ring (Cg3) [Cg2···Cg3i = 3.6065 (6) Å; Cg2—Cg3ii = 3.5274 (6) Å; symmetry codes: (i) 2-x, 1-y, 1-z; (ii) 2-x, -y, 1-z] together with O···O = 2.7226 (11) Å, O···N = 2.7072 (10) Å and N···O = 2.7072 (10)–2.8582 (12) Å short contacts. In the crystal packing, the molecules are stacked along the b axis and the adjacent molecules are linked by water molecules to form an infinite one dimensional chain along the [010] direction.

Related literature top

For related literature on hydrazones, see: Rollas & Küçükgüzel (2007); Singh et al. (1992); Ergenç & Günay (1998); Durgun et al. (1993). For related literature, see: Fun et al. (2008). For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

The title compound was obtained by refluxing 4-nitrrophenyl hydrazide (0.01 mol) and 4-(dimethylamino)benzaldehyde (0.01 mol) in ethanol (30 ml) with the addition of 3 drops of concentrated Sulfuric acid for 3 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with water and dried. Crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

Refinement top

The amino and water H atoms were located in a difference map and refined with restraints of N—H = 0.85 (1) and O—H = 0.84 (1) Å. The remaining H atoms were positioned geometrically [C—H = 0.93 (aromatic) or 0.96 Å (methyl)] and refined using a riding model, with Uiso(H) = 1.2Ueq(aromatic C) and 1.5Ueq(methyl C). A rotating-group model was used for 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 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis, showing infinite 1-D chains along the [010] direction.
N'-[(Z)-4-(Dimethylamino)benzylene]-4-nitrobenzohydrazide monohydrate top
Crystal data top
C16H16N4O3·H2OZ = 4
Mr = 330.34F(000) = 696
Triclinic, P1Dx = 1.427 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5866 (2) ÅCell parameters from 9891 reflections
b = 7.1337 (2) Åθ = 2.2–29.2°
c = 34.4059 (12) ŵ = 0.11 mm−1
α = 92.113 (2)°T = 100 K
β = 90.918 (2)°Block, red
γ = 107.816 (1)°0.41 × 0.13 × 0.10 mm
V = 1537.42 (8) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		11039 independent reflections
Radiation source: fine-focus sealed tube8656 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 32.5°, θmin = 0.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −9→9
Tmin = 0.959, Tmax = 0.990k = −10→10
52996 measured reflectionsl = −51→51
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0736P)2 + 0.5006P]
where P = (Fo2 + 2Fc2)/3
11039 reflections(Δ/σ)max = 0.001
461 parametersΔρmax = 0.45 e Å−3
8 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C16H16N4O3·H2Oγ = 107.816 (1)°
Mr = 330.34V = 1537.42 (8) Å3
Triclinic, P1Z = 4
a = 6.5866 (2) ÅMo Kα radiation
b = 7.1337 (2) ŵ = 0.11 mm−1
c = 34.4059 (12) ÅT = 100 K
α = 92.113 (2)°0.41 × 0.13 × 0.10 mm
β = 90.918 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		11039 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		8656 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.990Rint = 0.028
52996 measured reflectionsθmax = 32.5°
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155Δρmax = 0.45 e Å−3
S = 1.08Δρmin = −0.36 e Å−3
11039 reflectionsAbsolute structure: ?
461 parametersFlack parameter: ?
8 restraintsRogers parameter: ?
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1A0.70471 (11)−0.07582 (12)0.30351 (2)0.01918 (16)
O2A1.23137 (15)−0.24154 (16)0.46624 (3)0.0307 (2)
O3A1.53442 (13)−0.13214 (15)0.43817 (3)0.02754 (19)
N1A0.99847 (13)−0.03980 (13)0.26697 (2)0.01355 (15)
N2A0.89267 (13)−0.00979 (13)0.23380 (2)0.01426 (16)
N3A1.33845 (15)−0.17619 (14)0.43808 (3)0.01864 (17)
N4A0.71656 (14)0.20609 (14)0.05749 (2)0.01700 (17)
C1A1.24033 (15)−0.04368 (15)0.33741 (3)0.01467 (17)
H1AA1.31810.01190.31610.018*
C2A1.34633 (15)−0.06955 (15)0.37105 (3)0.01509 (18)
H2AA1.4945−0.03330.37250.018*
C3A1.22662 (15)−0.15040 (14)0.40243 (3)0.01401 (17)
C4A1.00511 (16)−0.20815 (15)0.40145 (3)0.01574 (18)
H4AA0.9283−0.26280.42290.019*
C5A0.90143 (15)−0.18208 (14)0.36758 (3)0.01475 (17)
H5AA0.7532−0.21920.36630.018*
C6A1.01742 (15)−0.10065 (14)0.33537 (3)0.01233 (16)
C7A0.89305 (15)−0.07167 (14)0.30049 (3)0.01324 (17)
C8A1.01208 (15)0.04600 (14)0.20449 (3)0.01353 (17)
H8AA1.15750.06370.20740.016*
C9A0.92940 (15)0.08245 (14)0.16715 (3)0.01250 (16)
C10A0.71074 (15)0.03692 (14)0.15792 (3)0.01435 (17)
H10A0.6115−0.01950.17640.017*
C11A0.64051 (15)0.07458 (15)0.12178 (3)0.01456 (17)
H11A0.49480.04210.11640.017*
C12A0.78608 (15)0.16157 (14)0.09285 (3)0.01284 (17)
C13A1.00565 (15)0.20405 (15)0.10204 (3)0.01502 (17)
H13A1.10570.25890.08360.018*
C14A1.07347 (15)0.16486 (15)0.13832 (3)0.01493 (17)
H14A1.21900.19410.14370.018*
C15A0.49080 (18)0.14199 (19)0.04745 (3)0.0236 (2)
H15A0.41640.19620.06640.035*
H15B0.43760.00070.04710.035*
H15C0.46870.18650.02220.035*
C16A0.86549 (18)0.26143 (18)0.02608 (3)0.0225 (2)
H16A0.98240.37450.03440.034*
H16B0.79390.29270.00390.034*
H16C0.91850.15370.01920.034*
O1B0.70699 (12)0.38412 (13)0.80186 (2)0.02177 (17)
O2B1.25253 (15)0.27622 (16)0.96674 (3)0.0316 (2)
O3B1.55367 (13)0.37835 (15)0.93778 (3)0.02784 (19)
N1B1.01061 (13)0.49010 (12)0.76799 (2)0.01420 (16)
N2B0.89598 (14)0.51210 (12)0.73516 (3)0.01539 (16)
N3B1.35800 (15)0.33755 (14)0.93811 (3)0.01923 (18)
N4B0.70414 (14)0.70854 (14)0.55794 (3)0.01718 (17)
C1B1.25594 (15)0.46004 (15)0.83674 (3)0.01543 (18)
H1BA1.33260.51040.81500.019*
C2B1.36291 (16)0.43702 (15)0.87055 (3)0.01629 (18)
H2BA1.51100.47140.87160.020*
C3B1.24511 (16)0.36207 (14)0.90255 (3)0.01464 (17)
C4B1.02391 (16)0.30698 (15)0.90212 (3)0.01653 (18)
H4BA0.94820.25580.92390.020*
C5B0.91904 (16)0.33052 (15)0.86818 (3)0.01572 (18)
H5BA0.77080.29460.86720.019*
C6B1.03316 (15)0.40749 (14)0.83543 (3)0.01277 (16)
C7B0.90385 (15)0.42761 (14)0.80052 (3)0.01407 (17)
C8B1.01092 (16)0.56375 (14)0.70506 (3)0.01526 (18)
H8BA1.15680.58300.70740.018*
C9B0.92289 (15)0.59328 (14)0.66764 (3)0.01363 (17)
C10B0.70382 (15)0.54404 (14)0.65874 (3)0.01446 (17)
H10B0.60590.48730.67740.017*
C11B0.63122 (15)0.57871 (15)0.62253 (3)0.01458 (17)
H11B0.48520.54450.61730.017*
C12B0.77534 (15)0.66547 (14)0.59329 (3)0.01311 (17)
C13B0.99531 (15)0.70948 (15)0.60209 (3)0.01521 (18)
H13B1.09410.76310.58340.018*
C14B1.06500 (15)0.67355 (14)0.63834 (3)0.01509 (18)
H14B1.21080.70360.64350.018*
C15B0.47861 (18)0.64283 (19)0.54800 (3)0.0242 (2)
H15D0.40350.69480.56720.036*
H15E0.42710.50140.54730.036*
H15F0.45550.68860.52290.036*
C16B0.85261 (18)0.76642 (18)0.52658 (3)0.0222 (2)
H16D0.96740.88130.53490.033*
H16E0.77970.79560.50430.033*
H16F0.90880.66070.51980.033*
O1W0.41887 (12)0.95772 (12)0.24824 (2)0.01787 (15)
O2W0.53340 (12)0.38228 (13)0.24783 (2)0.02204 (17)
H1NA1.1237 (17)−0.049 (3)0.2650 (5)0.037 (4)*
H2W20.485 (2)0.2591 (12)0.2452 (5)0.046 (5)*
H1W20.433 (2)0.429 (2)0.2445 (5)0.042 (5)*
H2W10.529 (2)0.962 (3)0.2618 (4)0.048 (5)*
H1NB1.1465 (14)0.523 (2)0.7656 (5)0.037 (4)*
H1W10.397 (3)0.860 (2)0.2324 (4)0.045 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0129 (3)0.0311 (4)0.0149 (3)0.0085 (3)−0.0005 (2)0.0032 (3)
O2A0.0315 (4)0.0487 (6)0.0149 (4)0.0152 (4)0.0023 (3)0.0136 (4)
O3A0.0207 (4)0.0431 (5)0.0213 (4)0.0132 (4)−0.0048 (3)0.0048 (4)
N1A0.0129 (3)0.0204 (4)0.0095 (3)0.0083 (3)−0.0012 (3)0.0024 (3)
N2A0.0162 (4)0.0191 (4)0.0093 (4)0.0082 (3)−0.0026 (3)0.0015 (3)
N3A0.0226 (4)0.0238 (4)0.0122 (4)0.0109 (3)−0.0022 (3)0.0033 (3)
N4A0.0198 (4)0.0230 (4)0.0093 (4)0.0078 (3)0.0004 (3)0.0048 (3)
C1A0.0142 (4)0.0188 (4)0.0115 (4)0.0056 (3)0.0002 (3)0.0019 (3)
C2A0.0142 (4)0.0206 (4)0.0118 (4)0.0074 (3)−0.0011 (3)0.0009 (3)
C3A0.0176 (4)0.0157 (4)0.0104 (4)0.0077 (3)−0.0020 (3)0.0013 (3)
C4A0.0173 (4)0.0172 (4)0.0135 (4)0.0059 (3)0.0017 (3)0.0049 (3)
C5A0.0140 (4)0.0169 (4)0.0134 (4)0.0045 (3)0.0003 (3)0.0036 (3)
C6A0.0138 (4)0.0137 (4)0.0107 (4)0.0060 (3)−0.0003 (3)0.0016 (3)
C7A0.0135 (4)0.0147 (4)0.0118 (4)0.0048 (3)−0.0007 (3)0.0011 (3)
C8A0.0143 (4)0.0155 (4)0.0115 (4)0.0055 (3)−0.0010 (3)0.0015 (3)
C9A0.0148 (4)0.0135 (4)0.0101 (4)0.0056 (3)−0.0003 (3)0.0016 (3)
C10A0.0146 (4)0.0181 (4)0.0106 (4)0.0051 (3)0.0007 (3)0.0032 (3)
C11A0.0131 (4)0.0189 (4)0.0119 (4)0.0051 (3)−0.0001 (3)0.0031 (3)
C12A0.0160 (4)0.0140 (4)0.0095 (4)0.0058 (3)0.0006 (3)0.0017 (3)
C13A0.0156 (4)0.0178 (4)0.0123 (4)0.0056 (3)0.0029 (3)0.0037 (3)
C14A0.0137 (4)0.0178 (4)0.0141 (4)0.0058 (3)0.0008 (3)0.0028 (3)
C15A0.0214 (5)0.0349 (6)0.0157 (5)0.0103 (4)−0.0034 (4)0.0056 (4)
C16A0.0262 (5)0.0283 (5)0.0126 (5)0.0070 (4)0.0032 (4)0.0062 (4)
O1B0.0149 (3)0.0334 (4)0.0173 (4)0.0079 (3)−0.0011 (3)0.0005 (3)
O2B0.0323 (5)0.0511 (6)0.0146 (4)0.0157 (4)0.0034 (3)0.0141 (4)
O3B0.0214 (4)0.0426 (5)0.0212 (4)0.0120 (4)−0.0036 (3)0.0068 (4)
N1B0.0150 (4)0.0176 (4)0.0107 (4)0.0059 (3)−0.0023 (3)0.0025 (3)
N2B0.0178 (4)0.0160 (4)0.0128 (4)0.0060 (3)−0.0045 (3)0.0013 (3)
N3B0.0235 (4)0.0235 (4)0.0130 (4)0.0104 (3)−0.0016 (3)0.0036 (3)
N4B0.0186 (4)0.0228 (4)0.0110 (4)0.0071 (3)0.0004 (3)0.0043 (3)
C1B0.0156 (4)0.0191 (4)0.0121 (4)0.0056 (3)0.0006 (3)0.0035 (3)
C2B0.0152 (4)0.0206 (4)0.0140 (4)0.0068 (3)−0.0005 (3)0.0035 (3)
C3B0.0193 (4)0.0158 (4)0.0104 (4)0.0077 (3)−0.0013 (3)0.0022 (3)
C4B0.0188 (4)0.0180 (4)0.0137 (4)0.0064 (3)0.0021 (3)0.0037 (3)
C5B0.0154 (4)0.0178 (4)0.0141 (4)0.0050 (3)0.0010 (3)0.0028 (3)
C6B0.0147 (4)0.0128 (4)0.0115 (4)0.0055 (3)−0.0011 (3)0.0004 (3)
C7B0.0158 (4)0.0147 (4)0.0121 (4)0.0055 (3)−0.0015 (3)−0.0005 (3)
C8B0.0173 (4)0.0155 (4)0.0135 (4)0.0060 (3)−0.0027 (3)0.0013 (3)
C9B0.0159 (4)0.0131 (4)0.0125 (4)0.0054 (3)−0.0014 (3)0.0009 (3)
C10B0.0165 (4)0.0163 (4)0.0106 (4)0.0047 (3)0.0004 (3)0.0034 (3)
C11B0.0143 (4)0.0174 (4)0.0122 (4)0.0048 (3)−0.0004 (3)0.0025 (3)
C12B0.0169 (4)0.0138 (4)0.0099 (4)0.0064 (3)0.0006 (3)0.0017 (3)
C13B0.0154 (4)0.0171 (4)0.0138 (4)0.0056 (3)0.0022 (3)0.0031 (3)
C14B0.0147 (4)0.0162 (4)0.0150 (4)0.0055 (3)−0.0003 (3)0.0022 (3)
C15B0.0203 (5)0.0376 (6)0.0161 (5)0.0105 (4)−0.0025 (4)0.0065 (4)
C16B0.0251 (5)0.0280 (5)0.0128 (5)0.0062 (4)0.0029 (4)0.0057 (4)
O1W0.0143 (3)0.0264 (4)0.0148 (3)0.0091 (3)−0.0012 (3)0.0013 (3)
O2W0.0165 (3)0.0271 (4)0.0234 (4)0.0074 (3)0.0002 (3)0.0056 (3)
Geometric parameters (Å, °) top
O1A—C7A1.2379 (11)O3B—N3B1.2317 (12)
O2A—N3A1.2278 (12)N1B—C7B1.3475 (13)
O3A—N3A1.2315 (12)N1B—N2B1.3888 (11)
N1A—C7A1.3462 (12)N1B—H1NB0.859 (9)
N1A—N2A1.3846 (11)N2B—C8B1.2899 (13)
N1A—H1NA0.850 (9)N3B—C3B1.4650 (13)
N2A—C8A1.2875 (12)N4B—C12B1.3753 (12)
N3A—C3A1.4667 (12)N4B—C15B1.4454 (14)
N4A—C12A1.3751 (12)N4B—C16B1.4527 (14)
N4A—C15A1.4475 (14)C1B—C2B1.3911 (13)
N4A—C16A1.4540 (13)C1B—C6B1.3985 (13)
C1A—C2A1.3892 (13)C1B—H1BA0.9300
C1A—C6A1.3983 (13)C2B—C3B1.3847 (14)
C1A—H1AA0.9300C2B—H2BA0.9300
C2A—C3A1.3838 (13)C3B—C4B1.3878 (14)
C2A—H2AA0.9300C4B—C5B1.3888 (14)
C3A—C4A1.3889 (13)C4B—H4BA0.9300
C4A—C5A1.3884 (13)C5B—C6B1.3988 (13)
C4A—H4AA0.9300C5B—H5BA0.9300
C5A—C6A1.3972 (13)C6B—C7B1.4978 (13)
C5A—H5AA0.9300C8B—C9B1.4524 (13)
C6A—C7A1.4981 (13)C8B—H8BA0.9300
C8A—C9A1.4505 (13)C9B—C14B1.4019 (13)
C8A—H8AA0.9300C9B—C10B1.4025 (13)
C9A—C14A1.4005 (13)C10B—C11B1.3847 (13)
C9A—C10A1.4043 (13)C10B—H10B0.9300
C10A—C11A1.3835 (13)C11B—C12B1.4189 (13)
C10A—H10A0.9300C11B—H11B0.9300
C11A—C12A1.4167 (13)C12B—C13B1.4107 (13)
C11A—H11A0.9300C13B—C14B1.3817 (13)
C12A—C13A1.4119 (13)C13B—H13B0.9300
C13A—C14A1.3857 (13)C14B—H14B0.9300
C13A—H13A0.9300C15B—H15D0.9600
C14A—H14A0.9300C15B—H15E0.9600
C15A—H15A0.9600C15B—H15F0.9600
C15A—H15B0.9600C16B—H16D0.9600
C15A—H15C0.9600C16B—H16E0.9600
C16A—H16A0.9600C16B—H16F0.9600
C16A—H16B0.9600O1W—H2W10.848 (9)
C16A—H16C0.9600O1W—H1W10.842 (9)
O1B—C7B1.2396 (12)O2W—H2W20.839 (8)
O2B—N3B1.2297 (12)O2W—H1W20.838 (8)
C7A—N1A—N2A118.95 (8)C7B—N1B—H1NB125.9 (11)
C7A—N1A—H1NA122.1 (12)N2B—N1B—H1NB115.4 (11)
N2A—N1A—H1NA118.7 (12)C8B—N2B—N1B113.95 (8)
C8A—N2A—N1A114.85 (8)O2B—N3B—O3B123.26 (9)
O2A—N3A—O3A123.44 (9)O2B—N3B—C3B118.35 (9)
O2A—N3A—C3A118.16 (9)O3B—N3B—C3B118.39 (9)
O3A—N3A—C3A118.40 (9)C12B—N4B—C15B119.95 (8)
C12A—N4A—C15A119.77 (8)C12B—N4B—C16B119.70 (9)
C12A—N4A—C16A119.76 (8)C15B—N4B—C16B117.92 (9)
C15A—N4A—C16A117.83 (9)C2B—C1B—C6B120.04 (9)
C2A—C1A—C6A120.39 (9)C2B—C1B—H1BA120.0
C2A—C1A—H1AA119.8C6B—C1B—H1BA120.0
C6A—C1A—H1AA119.8C3B—C2B—C1B118.87 (9)
C3A—C2A—C1A118.55 (9)C3B—C2B—H2BA120.6
C3A—C2A—H2AA120.7C1B—C2B—H2BA120.6
C1A—C2A—H2AA120.7C2B—C3B—C4B122.54 (9)
C2A—C3A—C4A122.60 (9)C2B—C3B—N3B118.80 (9)
C2A—C3A—N3A118.59 (9)C4B—C3B—N3B118.65 (9)
C4A—C3A—N3A118.82 (9)C3B—C4B—C5B118.02 (9)
C5A—C4A—C3A118.18 (9)C3B—C4B—H4BA121.0
C5A—C4A—H4AA120.9C5B—C4B—H4BA121.0
C3A—C4A—H4AA120.9C4B—C5B—C6B120.93 (9)
C4A—C5A—C6A120.71 (9)C4B—C5B—H5BA119.5
C4A—C5A—H5AA119.6C6B—C5B—H5BA119.5
C6A—C5A—H5AA119.6C1B—C6B—C5B119.59 (9)
C5A—C6A—C1A119.57 (8)C1B—C6B—C7B124.01 (9)
C5A—C6A—C7A117.17 (8)C5B—C6B—C7B116.40 (8)
C1A—C6A—C7A123.22 (8)O1B—C7B—N1B122.42 (9)
O1A—C7A—N1A123.57 (9)O1B—C7B—C6B120.50 (9)
O1A—C7A—C6A120.16 (9)N1B—C7B—C6B117.07 (8)
N1A—C7A—C6A116.26 (8)N2B—C8B—C9B122.99 (9)
N2A—C8A—C9A122.77 (9)N2B—C8B—H8BA118.5
N2A—C8A—H8AA118.6C9B—C8B—H8BA118.5
C9A—C8A—H8AA118.6C14B—C9B—C10B117.73 (9)
C14A—C9A—C10A117.64 (8)C14B—C9B—C8B118.20 (9)
C14A—C9A—C8A118.88 (8)C10B—C9B—C8B124.06 (9)
C10A—C9A—C8A123.48 (8)C11B—C10B—C9B120.92 (9)
C11A—C10A—C9A121.09 (9)C11B—C10B—H10B119.5
C11A—C10A—H10A119.5C9B—C10B—H10B119.5
C9A—C10A—H10A119.5C10B—C11B—C12B121.27 (9)
C10A—C11A—C12A121.35 (9)C10B—C11B—H11B119.4
C10A—C11A—H11A119.3C12B—C11B—H11B119.4
C12A—C11A—H11A119.3N4B—C12B—C13B121.07 (9)
N4A—C12A—C13A121.29 (8)N4B—C12B—C11B121.46 (9)
N4A—C12A—C11A121.36 (8)C13B—C12B—C11B117.46 (8)
C13A—C12A—C11A117.34 (8)C14B—C13B—C12B120.49 (9)
C14A—C13A—C12A120.62 (9)C14B—C13B—H13B119.8
C14A—C13A—H13A119.7C12B—C13B—H13B119.8
C12A—C13A—H13A119.7C13B—C14B—C9B122.08 (9)
C13A—C14A—C9A121.94 (9)C13B—C14B—H14B119.0
C13A—C14A—H14A119.0C9B—C14B—H14B119.0
C9A—C14A—H14A119.0N4B—C15B—H15D109.5
N4A—C15A—H15A109.5N4B—C15B—H15E109.5
N4A—C15A—H15B109.5H15D—C15B—H15E109.5
H15A—C15A—H15B109.5N4B—C15B—H15F109.5
N4A—C15A—H15C109.5H15D—C15B—H15F109.5
H15A—C15A—H15C109.5H15E—C15B—H15F109.5
H15B—C15A—H15C109.5N4B—C16B—H16D109.5
N4A—C16A—H16A109.5N4B—C16B—H16E109.5
N4A—C16A—H16B109.5H16D—C16B—H16E109.5
H16A—C16A—H16B109.5N4B—C16B—H16F109.5
N4A—C16A—H16C109.5H16D—C16B—H16F109.5
H16A—C16A—H16C109.5H16E—C16B—H16F109.5
H16B—C16A—H16C109.5H2W1—O1W—H1W1106.7 (12)
C7B—N1B—N2B118.62 (8)H2W2—O2W—H1W2108.6 (12)
C7A—N1A—N2A—C8A170.93 (9)C7B—N1B—N2B—C8B−176.98 (9)
C6A—C1A—C2A—C3A−0.75 (15)C6B—C1B—C2B—C3B−0.12 (15)
C1A—C2A—C3A—C4A0.60 (15)C1B—C2B—C3B—C4B0.67 (16)
C1A—C2A—C3A—N3A−179.48 (9)C1B—C2B—C3B—N3B179.87 (9)
O2A—N3A—C3A—C2A177.47 (10)O2B—N3B—C3B—C2B177.95 (10)
O3A—N3A—C3A—C2A−2.85 (15)O3B—N3B—C3B—C2B−2.44 (15)
O2A—N3A—C3A—C4A−2.60 (15)O2B—N3B—C3B—C4B−2.82 (15)
O3A—N3A—C3A—C4A177.07 (10)O3B—N3B—C3B—C4B176.80 (10)
C2A—C3A—C4A—C5A−0.35 (15)C2B—C3B—C4B—C5B−0.61 (16)
N3A—C3A—C4A—C5A179.73 (9)N3B—C3B—C4B—C5B−179.81 (9)
C3A—C4A—C5A—C6A0.25 (15)C3B—C4B—C5B—C6B0.00 (15)
C4A—C5A—C6A—C1A−0.42 (15)C2B—C1B—C6B—C5B−0.46 (15)
C4A—C5A—C6A—C7A−178.04 (9)C2B—C1B—C6B—C7B179.70 (9)
C2A—C1A—C6A—C5A0.68 (15)C4B—C5B—C6B—C1B0.53 (15)
C2A—C1A—C6A—C7A178.15 (9)C4B—C5B—C6B—C7B−179.62 (9)
N2A—N1A—C7A—O1A−0.01 (15)N2B—N1B—C7B—O1B1.99 (15)
N2A—N1A—C7A—C6A−179.29 (8)N2B—N1B—C7B—C6B−179.45 (8)
C5A—C6A—C7A—O1A16.42 (14)C1B—C6B—C7B—O1B−177.60 (10)
C1A—C6A—C7A—O1A−161.10 (10)C5B—C6B—C7B—O1B2.56 (14)
C5A—C6A—C7A—N1A−164.26 (9)C1B—C6B—C7B—N1B3.81 (14)
C1A—C6A—C7A—N1A18.21 (14)C5B—C6B—C7B—N1B−176.03 (9)
N1A—N2A—C8A—C9A179.26 (8)N1B—N2B—C8B—C9B179.47 (9)
N2A—C8A—C9A—C14A172.55 (9)N2B—C8B—C9B—C14B171.95 (9)
N2A—C8A—C9A—C10A−8.37 (15)N2B—C8B—C9B—C10B−8.92 (16)
C14A—C9A—C10A—C11A−0.81 (15)C14B—C9B—C10B—C11B−1.69 (14)
C8A—C9A—C10A—C11A−179.90 (9)C8B—C9B—C10B—C11B179.17 (9)
C9A—C10A—C11A—C12A−0.44 (15)C9B—C10B—C11B—C12B−0.18 (15)
C15A—N4A—C12A—C13A173.52 (10)C15B—N4B—C12B—C13B173.26 (10)
C16A—N4A—C12A—C13A12.30 (15)C16B—N4B—C12B—C13B11.36 (15)
C15A—N4A—C12A—C11A−7.65 (15)C15B—N4B—C12B—C11B−7.93 (15)
C16A—N4A—C12A—C11A−168.87 (9)C16B—N4B—C12B—C11B−169.83 (9)
C10A—C11A—C12A—N4A−177.42 (9)C10B—C11B—C12B—N4B−176.95 (9)
C10A—C11A—C12A—C13A1.46 (15)C10B—C11B—C12B—C13B1.91 (15)
N4A—C12A—C13A—C14A177.65 (9)N4B—C12B—C13B—C14B177.09 (9)
C11A—C12A—C13A—C14A−1.23 (14)C11B—C12B—C13B—C14B−1.76 (14)
C12A—C13A—C14A—C9A0.00 (15)C12B—C13B—C14B—C9B−0.10 (15)
C10A—C9A—C14A—C13A1.04 (15)C10B—C9B—C14B—C13B1.84 (15)
C8A—C9A—C14A—C13A−179.83 (9)C8B—C9B—C14B—C13B−178.97 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1Wi0.85 (1)2.02 (1)2.8582 (11)167.(2)
O2W—H2W2···O1Wii0.84 (1)2.07 (1)2.8892 (12)167.(2)
O2W—H1W2···N2Biii0.84 (1)2.44 (1)3.1989 (12)152.(2)
O2W—H1W2···O1Biii0.84 (1)2.45 (1)3.1535 (11)142.(2)
O1W—H2W1···O1Aiv0.85 (1)1.91 (1)2.7227 (10)161.(2)
O1W—H2W1···N2Aiv0.85 (1)2.55 (2)3.1072 (11)124.(1)
N1B—H1NB···O2Wv0.86 (1)2.07 (1)2.9260 (12)172.(2)
O1W—H1W1···O1Biii0.84 (1)2.00 (1)2.8304 (12)170.(2)
C1A—H1AA···O1Wi0.932.493.3025 (13)146
C8A—H8AA···O1Wi0.932.513.2886 (13)141
C1B—H1BA···O2Wv0.932.413.3276 (13)169
C5B—H5BA···O1B0.932.422.7555 (13)101
C8B—H8BA···O2Wv0.932.483.2977 (14)147
C15A—H15C···O2Bvi0.962.583.4738 (15)156
C15B—H15F···O2Avii0.962.583.4773 (15)156
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z; (v) −x+2, −y+1, −z+1; (vi) x−1, y, z−1; (vii) x−1, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1Wi0.85 (1)2.02 (1)2.8582 (11)167.(2)
O2W—H2W2···O1Wii0.84 (1)2.07 (1)2.8892 (12)167.(2)
O2W—H1W2···N2Biii0.84 (1)2.44 (1)3.1989 (12)152.(2)
O2W—H1W2···O1Biii0.84 (1)2.45 (1)3.1535 (11)142.(2)
O1W—H2W1···O1Aiv0.85 (1)1.91 (1)2.7227 (10)161.(2)
O1W—H2W1···N2Aiv0.85 (1)2.55 (2)3.1072 (11)124.(1)
N1B—H1NB···O2Wv0.86 (1)2.07 (1)2.9260 (12)172.(2)
O1W—H1W1···O1Biii0.84 (1)2.00 (1)2.8304 (12)170.(2)
C1A—H1AA···O1Wi0.932.493.3025 (13)146
C8A—H8AA···O1Wi0.932.513.2886 (13)141
C1B—H1BA···O2Wv0.932.413.3276 (13)169
C5B—H5BA···O1B0.932.422.7555 (13)101
C8B—H8BA···O2Wv0.932.483.2977 (14)147
C15A—H15C···O2Bvi0.962.583.4738 (15)156
C15B—H15F···O2Avii0.962.583.4773 (15)156
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z; (v) −x+2, −y+1, −z+1; (vi) x−1, y, z−1; (vii) x−1, y+1, z.
Acknowledgements top

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

references
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