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Acta Cryst. (2009). E65, o2065-o2066    [ doi:10.1107/S1600536809029833 ]

2-((E)-{2-[(E)-2,3-Dihydroxybenzylideneamino]-5-methylphenyl}iminiomethyl)-6-hydroxyphenolate

N. E. Eltayeb, S. G. Teoh, C. S. Yeap, H.-K. Fun and R. Adnan

Abstract top

The asymmetric unit of the title Schiff base compound, C21H18N2O4, consists of four independent zwitterions (A, B, C and D) with similar conformations. In each independent molecule, the methyl group is disordered over two positions; the occupancies of the two positions are 0.819 (5) and 0.181 (5) in molecule A, 0.912 (5) and 0.088 (5) in B, 0.734 (5) and 0.266 (5) in C, and 0.940 (6) and 0.060 (6) in D. The dihydroxyphenyl and the hydroxyphenolate rings in molecule A form dihedral angles of 17.36 (12) and 13.30 (12)°, respectively, with the central benzene ring, whereas the respective angles for molecules B, C and D are 30.22 (11)/7.46 (11), 35.26 (12)/11.01 (12) and 39.89 (12)/4.29 (12)°. In all independent molecules, intramolecular N-H...O and O-H...N hydrogen bonds generate S(6) ring motifs. The four independent molecules are linked into two pairs, viz. A-B and C-D, by intermolecular O-H...O hydrogen bonds. These pairs are linked into a two-dimensional network parallel to the ab plane by C-H...O hydrogen bonds. In addition, C-H...[pi] and [pi]-[pi] [centroid-centroid distance = 3.5153 (14)-3.7810 (15) Å] interactions stabilize the crystal structure.

Comment top

Schiff bases have received much attention because of their potential applications with some of these compounds exhibiting various pharmacological activities, as noted by their anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). Previously, we have reported the crystal structures of 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb et al., 2007a) and 6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007b). In this paper, we report the crystal structure of the title compound, obtained by the reaction of 4-methyl-1,2-phenylenediamine and 2,3-dihydroxybenzaldehyde.

The asymmetric unit of title compound consists of four crystallographically independent zwitterions A, B, C and D with almost similar conformations (Fig. 1 and Fig. 2). Each zwitterion is formed by the transfer one of the ortho-hydroxyl proton onto the adjacent imine unit resulting in the formation of iminium and hydroxyphenolate groups, with corresponding changes in the C20—O3, C14—N2 and C14—C15 bond lengths. These bonds are comparable to those in the related structure (Eltayeb et al., 2008). The dihydroxyphenyl ring [C1–C6] and the hydroxyphenolate ring [C15–C20] in molecule A form dihedral angles of 17.36 (12) and 13.30 (12)°, respectively, with the benzene ring (C8–C13) whereas these angles for molecules B, C and D are 30.22 (11)/7.46 (11)°, 35.26 (12)/11.01 (12)° and 39.89 (12)/4.29 (12)°, respectively.

In each independent molecule, each intramolecular N—H···O and O—H···N hydrogen bonds (Table 1) generate an S(6) ring motif (Bernstein et al., 1995). The four independent molecules are linked into two pairs, A/B and C/D via intermolecular O—H···O hydrogen bonds (Fig. 2 and Table 1). Intermolecular C—H···O interactions link these pairs of molecules into two-dimensional networks parallel to ab plane (Fig. 3). In addition, C—H···π (Table 1) and π–π interactions [Cg6···Cg8 = 3.5534 (14) Å, Cg3···Cg11iv = 3.5153 (14) Å, Cg7···Cg9iv = 3.7810 (15) Å, Cg1···Cg5iv = 3.7581 (15) Å and Cg4···Cg10iv = 3.7518 (15) Å, where Cg1, Cg3, Cg4, Cg5, Cg6, Cg7, Cg8, Cg9, Cg10 and Cg11 are centroids of C15A–C20A, C8B–C13B, C15B–C20B, C8C–C13C, C1D–C6D, C8A–C13A, C1C–C6C, C15C–C20C, C8D–C13D, C15D–C20D benzene rings, respectively] stabilize the crystal structure.

Related literature top

For the biological applications of Schiff base derivatives, see: Dao et al. (2000); Eltayeb & Ahmed (2005a,b); Karthikeyan et al. (2006); Sriram et al. (2006). For related structures, see: Eltayeb et al. (2007a,b, 2008). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C15A–C20A, C1B–C6B,

C8B–C13B, C15B–C20B, C8C–C13C and C1D–C6D rings, respectively.

Experimental top

A solution of 4-methyl-1,2-phenylenediamine (0.244 g, 2 mmol) in ethanol (20 ml) was added into 2,3-dihydroxybenzaldehyde (0.552 g, 4 mmol). The mixture was refluxed with stirring for 30 min. The resultant red solution was filtered. Red crystals suitable for X-ray analysis were formed after a few days of slow evaporation of the solvent at room temperature.

Refinement top

All O and N bound H atoms were located in a difference Fourier map and refined freely. The rest of the H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 or 0.96 Å and Uiso(H) = 1.2-1.5(methyl)Ueq(C). The rotating group model was applied for the methyl groups. The methyl group in each independent molecule is disordered over two positions, with refined site-occupancies of 0.819 (5) and 0.181 (5) for molecule A, 0.912 (5) and 0.088 (5) for B, 0.734 (5) and 0.266 (5) for C, and 0.940 (6) and 0.060 (6) for D. Atoms C21F and C21H were refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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. Molecule A of the title compound, with atom labels and 50% probability ellipsoids for non-H atoms. The other three independent molecules are labelled similarly. Intramolecular hydrogen bonds are shown as dashed lines. Both disorder components are shown.
[Figure 2] Fig. 2. The asymmetric unit of the title compound, showing four independent molecules. Displacement ellipsoids are drawn at the 20% probability level. For clarity, only O and N atoms are labelled. Intermolecular hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The crystal packing of the title compound, viewed down the c axis. Intermolecular hydrogen bonds are shown as dashed lines.
2-((E)-{2-[(E)-2,3-Dihydroxybenzylideneamino]-5- methylphenyl}iminiomethyl)-6-hydroxyphenolate top
Crystal data top
C21H18N2O4F(000) = 3040
Mr = 362.37Dx = 1.340 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9276 reflections
a = 17.0634 (2) Åθ = 2.2–29.6°
b = 21.3455 (2) ŵ = 0.09 mm−1
c = 20.0291 (2) ÅT = 100 K
β = 99.982 (1)°Block, red
V = 7184.70 (13) Å30.29 × 0.19 × 0.17 mm
Z = 16
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		12647 independent reflections
Radiation source: fine-focus sealed tube8172 reflections with I > 2σ(I)
graphiteRint = 0.069
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −20→20
Tmin = 0.920, Tmax = 0.984k = −25→25
67041 measured reflectionsl = −23→23
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) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0429P)2 + 2.6321P]
where P = (Fo2 + 2Fc2)/3
12647 reflections(Δ/σ)max = 0.001
1075 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C21H18N2O4V = 7184.70 (13) Å3
Mr = 362.37Z = 16
Monoclinic, P21/cMo Kα radiation
a = 17.0634 (2) ŵ = 0.09 mm−1
b = 21.3455 (2) ÅT = 100 K
c = 20.0291 (2) Å0.29 × 0.19 × 0.17 mm
β = 99.982 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		12647 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		8172 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.984Rint = 0.069
67041 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115Δρmax = 0.24 e Å−3
S = 1.03Δρmin = −0.22 e Å−3
12647 reflectionsAbsolute structure: ?
1075 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 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*/UeqOcc. (<1)
O1A1.19315 (10)0.46141 (9)0.86061 (9)0.0364 (5)
O2A1.03690 (10)0.47712 (8)0.86453 (9)0.0331 (4)
O3A0.91941 (9)0.51191 (9)0.75558 (9)0.0397 (5)
O4A0.97187 (13)0.53499 (12)0.63763 (11)0.0620 (7)
N1A0.91419 (11)0.45158 (9)0.92792 (10)0.0303 (5)
N2A0.80118 (13)0.48196 (10)0.81813 (12)0.0327 (5)
C1A1.08033 (13)0.44352 (11)0.91497 (12)0.0259 (5)
C2A1.16102 (13)0.43568 (12)0.91227 (12)0.0286 (6)
C3A1.20934 (14)0.40307 (12)0.96296 (12)0.0348 (6)
H3AA1.26300.39800.96100.042*
C4A1.17861 (15)0.37790 (14)1.01666 (13)0.0420 (7)
H4AA1.21160.35611.05060.050*
C5A1.09910 (14)0.38517 (13)1.01976 (13)0.0391 (7)
H5AA1.07870.36851.05610.047*
C6A1.04886 (13)0.41752 (11)0.96865 (12)0.0292 (6)
C7A0.96505 (14)0.42262 (12)0.97218 (13)0.0325 (6)
H7AA0.94690.40391.00860.039*
C8A0.83324 (14)0.45305 (11)0.93647 (14)0.0319 (6)
C9A0.80711 (15)0.44014 (12)0.99758 (14)0.0368 (6)
H9AA0.84430.43121.03610.044*
C10A0.72750 (15)0.44047 (12)1.00179 (15)0.0375 (7)
H10A0.71170.43101.04280.045*0.819 (5)
C11A0.67088 (15)0.45459 (11)0.94612 (15)0.0374 (7)
H11A0.61710.45450.94920.045*0.181 (5)
C12A0.69529 (14)0.46899 (11)0.88544 (15)0.0373 (7)
H12A0.65760.47950.84780.045*
C13A0.77596 (14)0.46789 (11)0.88016 (14)0.0330 (6)
C14A0.75666 (14)0.48370 (11)0.75795 (14)0.0338 (6)
H14A0.70290.47420.75450.041*
C15A0.78507 (14)0.49897 (11)0.69828 (13)0.0323 (6)
C16A0.73153 (16)0.50164 (12)0.63598 (15)0.0416 (7)
H16A0.67780.49340.63510.050*
C17A0.75728 (16)0.51593 (13)0.57788 (15)0.0457 (7)
H17A0.72110.51820.53750.055*
C18A0.83918 (17)0.52746 (13)0.57792 (14)0.0458 (7)
H18A0.85660.53690.53760.055*
C19A0.89239 (16)0.52477 (13)0.63700 (14)0.0418 (7)
C20A0.86793 (15)0.51179 (12)0.70029 (13)0.0351 (6)
C21A0.58355 (16)0.45353 (14)0.95249 (15)0.0316 (9)0.819 (5)
H21A0.57880.45500.99950.047*0.819 (5)
H21B0.55940.41580.93250.047*0.819 (5)
H21C0.55720.48920.92950.047*0.819 (5)
C21E0.6917 (9)0.4348 (8)1.0509 (7)0.045 (5)0.181 (5)
H21M0.72000.45711.08920.067*0.181 (5)
H21N0.68860.39131.06220.067*0.181 (5)
H21O0.63890.45161.03900.067*0.181 (5)
O1B−0.02790 (9)0.62281 (9)0.82457 (9)0.0343 (4)
O2B0.08476 (9)0.58736 (8)0.75073 (8)0.0323 (4)
O3B0.11961 (9)0.45970 (8)0.72811 (8)0.0287 (4)
O4B0.00762 (10)0.37802 (10)0.75534 (9)0.0380 (5)
N1B0.23622 (11)0.59434 (9)0.73336 (9)0.0262 (5)
N2B0.24301 (11)0.48183 (9)0.67198 (10)0.0253 (5)
C1B0.10696 (13)0.62649 (11)0.80378 (11)0.0255 (5)
C2B0.04828 (13)0.64443 (11)0.84062 (12)0.0269 (6)
C3B0.06718 (14)0.68648 (11)0.89352 (12)0.0285 (6)
H3BA0.02780.69960.91720.034*
C4B0.14418 (14)0.70940 (11)0.91184 (12)0.0287 (6)
H4BA0.15600.73760.94760.034*
C5B0.20283 (14)0.69050 (11)0.87721 (11)0.0278 (6)
H5BA0.25450.70540.89010.033*
C6B0.18514 (13)0.64872 (11)0.82217 (11)0.0251 (5)
C7B0.24725 (13)0.63130 (11)0.78509 (12)0.0272 (6)
H7BA0.29790.64760.79930.033*
C8B0.30034 (13)0.58367 (11)0.69796 (11)0.0254 (5)
C9B0.35955 (13)0.62756 (12)0.69341 (11)0.0294 (6)
H9BA0.35820.66640.71420.035*
C10B0.42014 (14)0.61392 (13)0.65826 (12)0.0322 (6)
H10B0.46000.64340.65680.039*0.912 (5)
C11B0.42286 (13)0.55688 (13)0.62487 (12)0.0326 (6)
H11B0.46360.54830.60090.039*0.088 (5)
C12B0.36306 (13)0.51301 (12)0.62826 (12)0.0298 (6)
H12B0.36360.47480.60590.036*
C13B0.30267 (13)0.52601 (12)0.66482 (11)0.0265 (6)
C14B0.23733 (13)0.42342 (12)0.65070 (12)0.0278 (6)
H14B0.27450.40850.62570.033*
C15B0.17722 (13)0.38248 (11)0.66421 (12)0.0266 (6)
C16B0.17535 (14)0.31955 (12)0.64055 (13)0.0355 (6)
H16B0.21260.30620.61480.043*
C17B0.11951 (15)0.27888 (13)0.65529 (13)0.0392 (7)
H17B0.11880.23770.63990.047*
C18B0.06269 (14)0.29908 (13)0.69389 (13)0.0361 (6)
H18B0.02440.27110.70350.043*
C19B0.06291 (13)0.35899 (12)0.71741 (12)0.0298 (6)
C20B0.12030 (13)0.40368 (12)0.70386 (12)0.0270 (6)
C21B0.48833 (16)0.54276 (13)0.58557 (15)0.0375 (9)0.912 (5)
H21D0.53020.57300.59670.056*0.912 (5)
H21E0.46760.54470.53790.056*0.912 (5)
H21F0.50900.50160.59700.056*0.912 (5)
C21F0.5082 (15)0.6287 (13)0.6610 (14)0.033 (8)*0.088 (5)
H21S0.51610.67320.66430.049*0.088 (5)
H21T0.52480.61360.62050.049*0.088 (5)
H21U0.53890.60870.69980.049*0.088 (5)
O1C0.61613 (10)0.65594 (9)0.39257 (10)0.0369 (5)
O2C0.46109 (10)0.63085 (8)0.39791 (8)0.0291 (4)
O3C0.34742 (9)0.67350 (8)0.28067 (8)0.0296 (4)
O4C0.40206 (10)0.69348 (9)0.16221 (10)0.0411 (5)
N1C0.33732 (11)0.65233 (9)0.45702 (9)0.0263 (5)
N2C0.22571 (12)0.65583 (9)0.34223 (10)0.0251 (5)
C1C0.50298 (13)0.66524 (11)0.44890 (11)0.0255 (5)
C2C0.58275 (14)0.67692 (11)0.44600 (12)0.0288 (6)
C3C0.62882 (14)0.70965 (13)0.49781 (13)0.0369 (6)
H3CA0.68250.71630.49670.044*
C4C0.59594 (15)0.73281 (13)0.55160 (13)0.0397 (7)
H4CA0.62780.75440.58650.048*
C5C0.51658 (14)0.72393 (12)0.55351 (12)0.0323 (6)
H5CA0.49460.74060.58900.039*
C6C0.46872 (13)0.68982 (11)0.50200 (11)0.0263 (5)
C7C0.38493 (14)0.68150 (11)0.50396 (12)0.0269 (6)
H7CA0.36460.69780.54050.032*
C8C0.25654 (13)0.64372 (11)0.46340 (12)0.0265 (6)
C9C0.23143 (15)0.63346 (12)0.52487 (13)0.0348 (6)
H9CA0.26860.63420.56480.042*
C10C0.15256 (16)0.62218 (13)0.52787 (14)0.0414 (7)
H10C0.13700.61630.56970.050*0.734 (5)
C11C0.09631 (15)0.61948 (13)0.46909 (14)0.0391 (7)
H11C0.04330.61100.47110.047*0.266 (5)
C12C0.12025 (14)0.62955 (12)0.40712 (13)0.0335 (6)
H12C0.08300.62780.36740.040*
C13C0.19956 (14)0.64221 (11)0.40397 (12)0.0265 (6)
C14C0.18110 (14)0.66724 (11)0.28360 (12)0.0280 (6)
H14C0.12610.66640.28090.034*
C15C0.21183 (13)0.68077 (11)0.22438 (12)0.0266 (6)
C16C0.15820 (15)0.69103 (12)0.16293 (13)0.0372 (7)
H16C0.10360.69050.16260.045*
C17C0.18628 (16)0.70164 (13)0.10459 (13)0.0399 (7)
H17C0.15090.70860.06440.048*
C18C0.26869 (15)0.70220 (12)0.10455 (13)0.0346 (6)
H18C0.28710.70880.06410.041*
C19C0.32201 (14)0.69329 (11)0.16285 (12)0.0297 (6)
C20C0.29569 (14)0.68228 (11)0.22574 (12)0.0262 (5)
C21C0.01231 (19)0.6010 (2)0.47405 (18)0.0451 (12)0.734 (5)
H21G0.00800.59500.52080.068*0.734 (5)
H21H−0.00100.56270.44950.068*0.734 (5)
H21I−0.02360.63350.45500.068*0.734 (5)
C21G0.1144 (6)0.6217 (6)0.5868 (5)0.047 (3)0.266 (5)
H21P0.14330.64830.62120.070*0.266 (5)
H21Q0.11370.57980.60390.070*0.266 (5)
H21R0.06080.63680.57460.070*0.266 (5)
O1D0.39194 (9)0.77129 (8)0.36623 (10)0.0343 (4)
O2D0.49820 (10)0.76787 (8)0.28054 (9)0.0335 (4)
O3D0.54298 (9)0.64355 (8)0.26057 (8)0.0321 (4)
O4D0.43246 (10)0.55434 (9)0.27391 (9)0.0377 (5)
N1D0.64614 (11)0.79038 (9)0.26308 (10)0.0306 (5)
N2D0.66987 (11)0.67631 (9)0.21144 (10)0.0253 (5)
C1D0.51759 (14)0.80222 (11)0.33813 (12)0.0284 (6)
C2D0.46195 (14)0.80328 (11)0.38153 (13)0.0304 (6)
C3D0.47734 (15)0.83798 (12)0.44060 (13)0.0355 (6)
H3DA0.44060.83850.46990.043*
C4D0.54770 (15)0.87227 (12)0.45641 (13)0.0379 (6)
H4DA0.55700.89660.49550.045*
C5D0.60308 (15)0.87034 (12)0.41466 (13)0.0357 (6)
H5DA0.65000.89310.42580.043*
C6D0.58983 (14)0.83434 (11)0.35500 (13)0.0307 (6)
C7D0.65207 (14)0.82724 (12)0.31460 (13)0.0320 (6)
H7DA0.69850.85040.32650.038*
C8D0.71118 (14)0.78384 (12)0.22887 (12)0.0304 (6)
C9D0.76177 (15)0.83227 (13)0.21815 (13)0.0400 (7)
H9DA0.75330.87220.23420.048*
C10D0.82403 (17)0.82238 (14)0.18438 (14)0.0463 (7)
H10D0.85720.85570.17820.056*0.940 (6)
C11D0.83857 (15)0.76391 (14)0.15938 (13)0.0398 (7)
H11D0.88120.75760.13690.048*0.060 (6)
C12D0.78779 (14)0.71468 (13)0.16874 (12)0.0341 (6)
H12D0.79640.67500.15230.041*
C13D0.72434 (13)0.72481 (12)0.20252 (12)0.0273 (6)
C14D0.66857 (13)0.61896 (12)0.18750 (12)0.0283 (6)
H14D0.70820.60740.16330.034*
C15D0.61139 (13)0.57423 (11)0.19609 (12)0.0268 (6)
C16D0.61550 (14)0.51327 (12)0.16815 (13)0.0354 (6)
H16D0.65580.50370.14390.042*
C17D0.56089 (14)0.46882 (12)0.17668 (13)0.0360 (6)
H17D0.56420.42900.15860.043*
C18D0.49948 (14)0.48311 (12)0.21279 (12)0.0303 (6)
H18D0.46260.45240.21840.036*
C19D0.49304 (13)0.54098 (11)0.23962 (11)0.0260 (6)
C20D0.54951 (13)0.58924 (11)0.23323 (11)0.0259 (6)
C21D0.90795 (16)0.75283 (15)0.12341 (16)0.0490 (10)0.940 (6)
H21J0.94320.78820.13020.074*0.940 (6)
H21K0.88880.74740.07580.074*0.940 (6)
H21L0.93600.71580.14130.074*0.940 (6)
C21H0.900 (4)0.848 (3)0.164 (3)0.08 (2)*0.060 (6)
H21V0.91730.88420.19130.127*0.060 (6)
H21W0.88950.85960.11720.127*0.060 (6)
H21X0.94050.81650.17140.127*0.060 (6)
H1OA1.161 (2)0.4665 (16)0.8211 (17)0.085 (12)*
H1OB−0.0314 (16)0.5904 (14)0.7999 (14)0.050 (10)*
H1OC0.581 (2)0.6478 (17)0.3561 (18)0.094 (14)*
H1OD0.396 (2)0.7436 (16)0.3327 (17)0.085 (12)*
H2OA0.9859 (19)0.4770 (15)0.8730 (16)0.081 (11)*
H2OB0.1312 (17)0.5778 (13)0.7319 (14)0.061 (9)*
H2OC0.4060 (18)0.6322 (14)0.4069 (15)0.072 (10)*
H2OD0.5446 (18)0.7653 (14)0.2607 (15)0.065 (10)*
H4OA0.997 (3)0.533 (2)0.676 (2)0.130 (19)*
H4OB0.014 (2)0.4197 (17)0.7643 (17)0.088 (13)*
H4OC0.426 (2)0.6875 (19)0.2045 (19)0.110 (15)*
H4OD0.436 (2)0.5922 (16)0.2872 (17)0.082 (13)*
H2NA0.8542 (18)0.4897 (14)0.8169 (14)0.062 (9)*
H2NB0.1992 (18)0.4912 (14)0.6998 (14)0.072 (10)*
H2NC0.2810 (15)0.6585 (11)0.3414 (12)0.040 (7)*
H2ND0.6257 (16)0.6842 (12)0.2352 (13)0.051 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0209 (9)0.0591 (13)0.0297 (11)−0.0017 (9)0.0056 (9)0.0028 (9)
O2A0.0201 (9)0.0424 (11)0.0371 (10)0.0054 (8)0.0054 (8)0.0064 (9)
O3A0.0271 (9)0.0517 (12)0.0368 (11)−0.0115 (9)−0.0041 (9)0.0051 (9)
O4A0.0430 (13)0.104 (2)0.0374 (13)−0.0274 (12)0.0013 (11)0.0070 (13)
N1A0.0220 (11)0.0296 (12)0.0395 (13)−0.0022 (9)0.0060 (10)−0.0041 (10)
N2A0.0201 (11)0.0263 (12)0.0493 (15)−0.0004 (9)−0.0012 (11)0.0061 (10)
C1A0.0212 (12)0.0264 (14)0.0287 (14)0.0022 (10)0.0000 (11)−0.0029 (11)
C2A0.0210 (12)0.0400 (16)0.0247 (13)0.0009 (11)0.0033 (11)−0.0030 (12)
C3A0.0195 (12)0.0508 (18)0.0330 (15)0.0020 (12)0.0015 (12)−0.0022 (13)
C4A0.0285 (14)0.060 (2)0.0360 (16)0.0028 (13)0.0011 (12)0.0113 (14)
C5A0.0296 (14)0.0522 (19)0.0358 (16)−0.0038 (13)0.0067 (13)0.0089 (14)
C6A0.0211 (12)0.0323 (15)0.0339 (15)0.0004 (11)0.0034 (11)−0.0005 (12)
C7A0.0240 (13)0.0358 (16)0.0393 (16)0.0007 (12)0.0101 (12)0.0021 (13)
C8A0.0213 (13)0.0260 (15)0.0487 (17)0.0010 (11)0.0068 (13)−0.0011 (12)
C9A0.0314 (14)0.0347 (16)0.0466 (17)0.0006 (12)0.0132 (13)−0.0049 (13)
C10A0.0285 (14)0.0337 (16)0.0525 (18)−0.0009 (12)0.0128 (14)−0.0038 (14)
C11A0.0291 (14)0.0231 (15)0.064 (2)−0.0011 (11)0.0198 (15)0.0003 (13)
C12A0.0239 (13)0.0250 (15)0.0611 (19)0.0034 (11)0.0021 (13)0.0035 (13)
C13A0.0278 (14)0.0209 (14)0.0528 (17)−0.0013 (11)0.0140 (13)0.0039 (12)
C14A0.0216 (13)0.0214 (14)0.0567 (19)−0.0001 (11)0.0022 (14)0.0020 (13)
C15A0.0264 (13)0.0189 (14)0.0465 (17)−0.0007 (11)−0.0081 (13)−0.0033 (12)
C16A0.0341 (15)0.0325 (17)0.0541 (19)−0.0015 (12)−0.0038 (14)−0.0025 (14)
C17A0.0420 (17)0.0375 (17)0.0480 (19)0.0023 (14)−0.0187 (15)−0.0061 (14)
C18A0.0564 (19)0.0385 (18)0.0376 (17)−0.0058 (14)−0.0060 (15)−0.0007 (13)
C19A0.0370 (16)0.0421 (18)0.0427 (17)−0.0107 (13)−0.0032 (14)−0.0004 (14)
C20A0.0355 (15)0.0308 (16)0.0364 (16)−0.0059 (12)−0.0007 (13)0.0021 (12)
C21A0.0231 (16)0.035 (2)0.0370 (19)0.0034 (14)0.0049 (14)0.0114 (15)
C21E0.055 (10)0.054 (11)0.034 (9)−0.007 (8)0.032 (8)−0.009 (8)
O1B0.0224 (9)0.0408 (12)0.0392 (11)−0.0016 (8)0.0038 (8)−0.0051 (10)
O2B0.0224 (9)0.0391 (11)0.0353 (10)−0.0022 (8)0.0045 (8)−0.0096 (9)
O3B0.0265 (9)0.0287 (10)0.0308 (9)−0.0024 (7)0.0046 (8)−0.0038 (8)
O4B0.0315 (10)0.0412 (12)0.0421 (11)−0.0112 (9)0.0092 (9)−0.0074 (10)
N1B0.0233 (10)0.0295 (12)0.0257 (11)−0.0024 (9)0.0040 (9)0.0008 (10)
N2B0.0213 (10)0.0284 (13)0.0249 (11)−0.0006 (9)0.0005 (9)−0.0005 (9)
C1B0.0281 (13)0.0237 (14)0.0234 (13)0.0000 (11)0.0005 (11)0.0010 (11)
C2B0.0226 (13)0.0274 (14)0.0296 (14)0.0017 (11)0.0014 (11)0.0069 (11)
C3B0.0295 (13)0.0294 (15)0.0272 (14)0.0050 (11)0.0064 (11)0.0059 (12)
C4B0.0366 (14)0.0235 (14)0.0253 (13)−0.0002 (11)0.0040 (12)0.0020 (11)
C5B0.0266 (13)0.0289 (15)0.0264 (13)−0.0038 (11)0.0001 (11)0.0028 (11)
C6B0.0264 (13)0.0235 (14)0.0255 (13)−0.0002 (10)0.0047 (11)0.0043 (11)
C7B0.0224 (12)0.0306 (15)0.0270 (14)−0.0054 (11)0.0001 (11)0.0039 (12)
C8B0.0194 (12)0.0324 (15)0.0231 (13)−0.0010 (11)0.0006 (10)0.0022 (11)
C9B0.0299 (13)0.0344 (15)0.0228 (13)−0.0064 (11)0.0018 (11)0.0021 (11)
C10B0.0255 (13)0.0451 (17)0.0251 (13)−0.0058 (12)0.0022 (11)0.0060 (13)
C11B0.0219 (13)0.0464 (17)0.0298 (14)0.0047 (12)0.0056 (11)0.0133 (13)
C12B0.0266 (13)0.0358 (16)0.0261 (14)0.0054 (11)0.0022 (11)0.0048 (11)
C13B0.0198 (12)0.0369 (16)0.0218 (13)−0.0023 (11)0.0011 (10)0.0070 (11)
C14B0.0211 (12)0.0366 (16)0.0238 (13)0.0049 (11)−0.0011 (11)−0.0008 (12)
C15B0.0198 (12)0.0281 (15)0.0287 (14)0.0012 (10)−0.0045 (11)−0.0007 (11)
C16B0.0259 (13)0.0373 (17)0.0408 (16)0.0034 (12)−0.0010 (12)−0.0083 (13)
C17B0.0347 (15)0.0315 (16)0.0462 (17)−0.0004 (12)−0.0077 (13)−0.0083 (13)
C18B0.0281 (14)0.0375 (17)0.0395 (16)−0.0079 (12)−0.0028 (12)−0.0031 (13)
C19B0.0219 (13)0.0362 (16)0.0285 (14)−0.0037 (11)−0.0033 (11)0.0007 (12)
C20B0.0223 (12)0.0302 (15)0.0256 (13)−0.0011 (11)−0.0037 (11)−0.0008 (11)
C21B0.0323 (16)0.0345 (18)0.0495 (19)0.0055 (13)0.0175 (15)0.0062 (14)
O1C0.0245 (10)0.0464 (12)0.0390 (11)0.0054 (8)0.0035 (9)−0.0122 (9)
O2C0.0237 (9)0.0327 (10)0.0288 (10)0.0025 (8)−0.0011 (8)−0.0074 (8)
O3C0.0229 (9)0.0368 (10)0.0267 (9)−0.0018 (7)−0.0021 (8)0.0042 (8)
O4C0.0310 (10)0.0567 (13)0.0360 (12)−0.0101 (9)0.0069 (9)0.0044 (10)
N1C0.0255 (11)0.0289 (12)0.0237 (11)0.0034 (9)0.0020 (9)0.0028 (9)
N2C0.0236 (11)0.0236 (12)0.0271 (12)0.0001 (9)0.0014 (10)0.0010 (9)
C1C0.0266 (13)0.0252 (14)0.0219 (13)0.0038 (11)−0.0038 (11)−0.0002 (11)
C2C0.0263 (13)0.0310 (15)0.0272 (14)0.0065 (11)−0.0003 (11)−0.0008 (12)
C3C0.0225 (13)0.0478 (18)0.0374 (16)0.0005 (12)−0.0035 (12)−0.0044 (14)
C4C0.0346 (15)0.0492 (18)0.0309 (15)−0.0034 (13)−0.0068 (13)−0.0050 (13)
C5C0.0346 (15)0.0368 (16)0.0238 (14)0.0034 (12)0.0006 (12)−0.0023 (12)
C6C0.0280 (13)0.0260 (14)0.0233 (13)0.0052 (11)−0.0001 (11)0.0025 (11)
C7C0.0318 (14)0.0259 (14)0.0227 (13)0.0040 (11)0.0036 (11)0.0034 (11)
C8C0.0256 (13)0.0244 (14)0.0294 (14)0.0017 (10)0.0049 (11)0.0013 (11)
C9C0.0386 (15)0.0385 (16)0.0271 (14)−0.0011 (12)0.0047 (12)0.0030 (12)
C10C0.0397 (16)0.0514 (19)0.0362 (16)−0.0084 (14)0.0152 (14)0.0001 (14)
C11C0.0289 (14)0.0431 (17)0.0467 (17)−0.0053 (12)0.0106 (13)−0.0028 (14)
C12C0.0244 (13)0.0367 (16)0.0377 (15)−0.0036 (11)0.0009 (12)0.0002 (13)
C13C0.0280 (13)0.0220 (14)0.0302 (14)0.0027 (10)0.0068 (11)0.0019 (11)
C14C0.0253 (13)0.0261 (14)0.0304 (14)0.0000 (11)−0.0014 (11)−0.0016 (11)
C15C0.0260 (13)0.0246 (14)0.0278 (14)−0.0014 (10)0.0007 (11)0.0011 (11)
C16C0.0274 (14)0.0459 (18)0.0347 (16)0.0000 (12)−0.0046 (12)0.0028 (13)
C17C0.0402 (16)0.0441 (18)0.0313 (15)−0.0036 (13)−0.0055 (13)0.0060 (13)
C18C0.0446 (16)0.0317 (16)0.0268 (14)−0.0077 (12)0.0044 (13)0.0042 (12)
C19C0.0316 (14)0.0268 (15)0.0299 (14)−0.0058 (11)0.0037 (12)0.0002 (11)
C20C0.0297 (13)0.0181 (13)0.0288 (14)−0.0019 (10)−0.0002 (11)0.0006 (11)
C21C0.027 (2)0.069 (3)0.038 (2)−0.0055 (19)0.0046 (17)0.009 (2)
C21G0.036 (6)0.076 (9)0.027 (6)−0.005 (6)0.004 (5)0.019 (6)
O1D0.0259 (9)0.0301 (11)0.0460 (12)0.0031 (8)0.0037 (9)0.0005 (9)
O2D0.0280 (10)0.0285 (10)0.0428 (11)−0.0005 (8)0.0026 (9)−0.0054 (8)
O3D0.0330 (9)0.0264 (10)0.0377 (10)−0.0069 (8)0.0088 (8)−0.0068 (8)
O4D0.0372 (11)0.0342 (12)0.0443 (12)−0.0134 (9)0.0142 (9)−0.0092 (9)
N1D0.0303 (11)0.0249 (12)0.0353 (12)−0.0005 (9)0.0023 (10)0.0026 (10)
N2D0.0194 (10)0.0268 (12)0.0281 (11)−0.0023 (9)−0.0001 (9)0.0025 (10)
C1D0.0295 (14)0.0194 (14)0.0334 (15)0.0044 (11)−0.0026 (12)0.0021 (11)
C2D0.0280 (14)0.0214 (14)0.0402 (16)0.0075 (11)0.0012 (12)0.0050 (12)
C3D0.0332 (15)0.0326 (16)0.0401 (16)0.0090 (12)0.0045 (13)0.0037 (13)
C4D0.0379 (15)0.0357 (16)0.0376 (16)0.0047 (13)0.0000 (13)−0.0030 (13)
C5D0.0297 (14)0.0316 (16)0.0422 (16)0.0020 (12)−0.0041 (13)−0.0013 (13)
C6D0.0291 (14)0.0248 (14)0.0359 (15)0.0052 (11)−0.0009 (12)0.0028 (12)
C7D0.0254 (13)0.0279 (15)0.0390 (16)−0.0023 (11)−0.0046 (12)0.0068 (13)
C8D0.0268 (13)0.0299 (15)0.0325 (14)−0.0041 (11)−0.0002 (12)0.0051 (12)
C9D0.0459 (16)0.0308 (16)0.0434 (17)−0.0101 (13)0.0081 (14)0.0021 (13)
C10D0.0480 (17)0.0411 (19)0.0511 (18)−0.0148 (14)0.0119 (15)0.0058 (15)
C11D0.0280 (14)0.0517 (19)0.0397 (16)−0.0071 (13)0.0061 (13)0.0080 (14)
C12D0.0263 (13)0.0379 (16)0.0361 (15)−0.0034 (12)−0.0001 (12)0.0007 (12)
C13D0.0177 (12)0.0352 (16)0.0258 (13)−0.0049 (11)−0.0047 (10)0.0057 (11)
C14D0.0198 (12)0.0322 (16)0.0313 (14)0.0038 (11)0.0004 (11)−0.0012 (12)
C15D0.0186 (12)0.0279 (15)0.0314 (14)0.0004 (10)−0.0024 (11)0.0006 (11)
C16D0.0247 (13)0.0331 (16)0.0475 (17)0.0048 (12)0.0040 (12)−0.0042 (13)
C17D0.0321 (14)0.0210 (14)0.0506 (17)0.0035 (12)−0.0049 (13)−0.0070 (13)
C18D0.0249 (13)0.0267 (15)0.0352 (15)−0.0033 (11)−0.0062 (11)0.0011 (12)
C19D0.0229 (12)0.0288 (15)0.0247 (13)−0.0034 (11)−0.0006 (11)0.0020 (11)
C20D0.0240 (13)0.0251 (15)0.0255 (13)0.0002 (11)−0.0039 (11)0.0016 (11)
C21D0.0363 (17)0.056 (2)0.059 (2)−0.0139 (15)0.0185 (16)−0.0038 (17)
Geometric parameters (Å, °) top
O1A—C2A1.367 (3)O1C—C2C1.372 (3)
O1A—H1OA0.89 (3)O1C—H1OC0.87 (4)
O2A—C1A1.351 (3)O2C—C1C1.356 (3)
O2A—H2OA0.91 (3)O2C—H2OC0.99 (3)
O3A—C20A1.289 (3)O3C—C20C1.299 (3)
O4A—C19A1.372 (3)O4C—C19C1.368 (3)
O4A—H4OA0.81 (4)O4C—H4OC0.89 (4)
N1A—C7A1.286 (3)N1C—C7C1.291 (3)
N1A—C8A1.421 (3)N1C—C8C1.418 (3)
N2A—C14A1.309 (3)N2C—C14C1.307 (3)
N2A—C13A1.416 (3)N2C—C13C1.416 (3)
N2A—H2NA0.92 (3)N2C—H2NC0.95 (2)
C1A—C2A1.397 (3)C1C—C2C1.395 (3)
C1A—C6A1.397 (3)C1C—C6C1.401 (3)
C2A—C3A1.380 (3)C2C—C3C1.378 (3)
C3A—C4A1.384 (3)C3C—C4C1.389 (3)
C3A—H3AA0.93C3C—H3CA0.93
C4A—C5A1.378 (3)C4C—C5C1.375 (3)
C4A—H4AA0.93C4C—H4CA0.93
C5A—C6A1.398 (3)C5C—C6C1.403 (3)
C5A—H5AA0.93C5C—H5CA0.93
C6A—C7A1.448 (3)C6C—C7C1.448 (3)
C7A—H7AA0.93C7C—H7CA0.93
C8A—C13A1.395 (3)C8C—C9C1.389 (3)
C8A—C9A1.401 (3)C8C—C13C1.401 (3)
C9A—C10A1.376 (3)C9C—C10C1.379 (3)
C9A—H9AA0.93C9C—H9CA0.93
C10A—C21E1.251 (12)C10C—C11C1.385 (4)
C10A—C11A1.376 (4)C10C—C21G1.445 (9)
C10A—H10A0.93C10C—H10C0.93
C11A—C12A1.386 (3)C11C—C12C1.389 (3)
C11A—C21A1.518 (3)C11C—C21C1.506 (4)
C11A—H11A0.93C11C—H11C0.93
C12A—C13A1.399 (3)C12C—C13C1.392 (3)
C12A—H12A0.93C12C—H12C0.93
C14A—C15A1.404 (3)C14C—C15C1.407 (3)
C14A—H14A0.93C14C—H14C0.93
C15A—C16A1.414 (4)C15C—C16C1.418 (3)
C15A—C20A1.434 (3)C15C—C20C1.427 (3)
C16A—C17A1.348 (4)C16C—C17C1.357 (3)
C16A—H16A0.93C16C—H16C0.93
C17A—C18A1.419 (4)C17C—C18C1.406 (3)
C17A—H17A0.93C17C—H17C0.93
C18A—C19A1.362 (4)C18C—C19C1.364 (3)
C18A—H18A0.93C18C—H18C0.93
C19A—C20A1.429 (3)C19C—C20C1.428 (3)
C21A—H21A0.96C21C—H21G0.96
C21A—H21B0.96C21C—H21H0.96
C21A—H21C0.96C21C—H21I0.96
C21E—H21M0.96C21G—H21P0.96
C21E—H21N0.96C21G—H21Q0.96
C21E—H21O0.96C21G—H21R0.96
O1B—C2B1.364 (3)O1D—C2D1.364 (3)
O1B—H1OB0.85 (3)O1D—H1OD0.91 (3)
O2B—C1B1.353 (3)O2D—C1D1.358 (3)
O2B—H2OB0.96 (3)O2D—H2OD0.95 (3)
O3B—C20B1.292 (3)O3D—C20D1.295 (3)
O4B—C19B1.371 (3)O4D—C19D1.367 (3)
O4B—H4OB0.91 (4)O4D—H4OD0.85 (3)
N1B—C7B1.290 (3)N1D—C7D1.288 (3)
N1B—C8B1.422 (3)N1D—C8D1.409 (3)
N2B—C14B1.316 (3)N2D—C14D1.313 (3)
N2B—C13B1.413 (3)N2D—C13D1.423 (3)
N2B—H2NB1.03 (3)N2D—H2ND0.97 (3)
C1B—C2B1.396 (3)C1D—C2D1.394 (3)
C1B—C6B1.404 (3)C1D—C6D1.400 (3)
C2B—C3B1.383 (3)C2D—C3D1.382 (3)
C3B—C4B1.390 (3)C3D—C4D1.395 (3)
C3B—H3BA0.93C3D—H3DA0.93
C4B—C5B1.373 (3)C4D—C5D1.367 (3)
C4B—H4BA0.93C4D—H4DA0.93
C5B—C6B1.409 (3)C5D—C6D1.406 (3)
C5B—H5BA0.93C5D—H5DA0.93
C6B—C7B1.444 (3)C6D—C7D1.450 (3)
C7B—H7BA0.93C7D—H7DA0.93
C8B—C9B1.392 (3)C8D—C9D1.387 (3)
C8B—C13B1.402 (3)C8D—C13D1.399 (3)
C9B—C10B1.379 (3)C9D—C10D1.371 (4)
C9B—H9BA0.93C9D—H9DA0.93
C10B—C11B1.394 (4)C10D—C11D1.383 (4)
C10B—C21F1.53 (3)C10D—C21H1.52 (6)
C10B—H10B0.93C10D—H10D0.93
C11B—C12B1.395 (3)C11D—C12D1.395 (3)
C11B—C21B1.504 (3)C11D—C21D1.507 (3)
C11B—H11B0.93C11D—H11D0.93
C12B—C13B1.392 (3)C12D—C13D1.390 (3)
C12B—H12B0.93C12D—H12D0.93
C14B—C15B1.409 (3)C14D—C15D1.397 (3)
C14B—H14B0.93C14D—H14D0.93
C15B—C16B1.423 (3)C15D—C16D1.423 (3)
C15B—C20B1.430 (3)C15D—C20D1.429 (3)
C16B—C17B1.359 (3)C16D—C17D1.361 (3)
C16B—H16B0.93C16D—H16D0.93
C17B—C18B1.408 (3)C17D—C18D1.406 (3)
C17B—H17B0.93C17D—H17D0.93
C18B—C19B1.363 (3)C18D—C19D1.359 (3)
C18B—H18B0.93C18D—H18D0.93
C19B—C20B1.426 (3)C19D—C20D1.431 (3)
C21B—H21D0.96C21D—H21J0.96
C21B—H21E0.96C21D—H21K0.96
C21B—H21F0.96C21D—H21L0.96
C21F—H21S0.96C21H—H21V0.96
C21F—H21T0.96C21H—H21W0.96
C21F—H21U0.96C21H—H21X0.96
C2A—O1A—H1OA117 (2)C2C—O1C—H1OC114 (2)
C1A—O2A—H2OA106 (2)C1C—O2C—H2OC104.0 (18)
C19A—O4A—H4OA111 (3)C19C—O4C—H4OC107 (2)
C7A—N1A—C8A118.8 (2)C7C—N1C—C8C119.7 (2)
C14A—N2A—C13A126.7 (2)C14C—N2C—C13C126.9 (2)
C14A—N2A—H2NA112.6 (18)C14C—N2C—H2NC113.5 (15)
C13A—N2A—H2NA120.6 (18)C13C—N2C—H2NC119.6 (15)
O2A—C1A—C2A116.8 (2)O2C—C1C—C2C117.1 (2)
O2A—C1A—C6A123.5 (2)O2C—C1C—C6C122.6 (2)
C2A—C1A—C6A119.7 (2)C2C—C1C—C6C120.2 (2)
O1A—C2A—C3A119.5 (2)O1C—C2C—C3C119.5 (2)
O1A—C2A—C1A120.5 (2)O1C—C2C—C1C120.9 (2)
C3A—C2A—C1A119.9 (2)C3C—C2C—C1C119.5 (2)
C2A—C3A—C4A120.6 (2)C2C—C3C—C4C120.7 (2)
C2A—C3A—H3AA119.7C2C—C3C—H3CA119.7
C4A—C3A—H3AA119.7C4C—C3C—H3CA119.7
C5A—C4A—C3A120.0 (2)C5C—C4C—C3C120.3 (2)
C5A—C4A—H4AA120.0C5C—C4C—H4CA119.8
C3A—C4A—H4AA120.0C3C—C4C—H4CA119.8
C4A—C5A—C6A120.4 (2)C4C—C5C—C6C120.1 (2)
C4A—C5A—H5AA119.8C4C—C5C—H5CA119.9
C6A—C5A—H5AA119.8C6C—C5C—H5CA119.9
C1A—C6A—C5A119.4 (2)C1C—C6C—C5C119.1 (2)
C1A—C6A—C7A121.5 (2)C1C—C6C—C7C121.2 (2)
C5A—C6A—C7A119.1 (2)C5C—C6C—C7C119.7 (2)
N1A—C7A—C6A123.8 (2)N1C—C7C—C6C122.6 (2)
N1A—C7A—H7AA118.1N1C—C7C—H7CA118.7
C6A—C7A—H7AA118.1C6C—C7C—H7CA118.7
C13A—C8A—C9A117.8 (2)C9C—C8C—C13C118.3 (2)
C13A—C8A—N1A117.8 (2)C9C—C8C—N1C123.6 (2)
C9A—C8A—N1A124.3 (2)C13C—C8C—N1C118.0 (2)
C10A—C9A—C8A121.3 (3)C10C—C9C—C8C121.3 (2)
C10A—C9A—H9AA119.3C10C—C9C—H9CA119.4
C8A—C9A—H9AA119.3C8C—C9C—H9CA119.4
C21E—C10A—C9A132.1 (8)C9C—C10C—C11C120.5 (2)
C21E—C10A—C11A106.8 (8)C9C—C10C—C21G128.2 (5)
C9A—C10A—C11A120.9 (3)C11C—C10C—C21G110.5 (5)
C9A—C10A—H10A119.6C9C—C10C—H10C119.7
C11A—C10A—H10A119.6C11C—C10C—H10C119.7
C10A—C11A—C12A118.9 (2)C10C—C11C—C12C119.0 (2)
C10A—C11A—C21A119.4 (2)C10C—C11C—C21C118.8 (3)
C12A—C11A—C21A121.7 (3)C12C—C11C—C21C122.0 (3)
C10A—C11A—H11A120.5C10C—C11C—H11C120.5
C12A—C11A—H11A120.5C12C—C11C—H11C120.5
C11A—C12A—C13A120.8 (3)C11C—C12C—C13C120.6 (2)
C11A—C12A—H12A119.6C11C—C12C—H12C119.7
C13A—C12A—H12A119.6C13C—C12C—H12C119.7
C8A—C13A—C12A120.2 (2)C12C—C13C—C8C120.2 (2)
C8A—C13A—N2A118.7 (2)C12C—C13C—N2C122.4 (2)
C12A—C13A—N2A121.0 (2)C8C—C13C—N2C117.4 (2)
N2A—C14A—C15A124.0 (2)N2C—C14C—C15C123.5 (2)
N2A—C14A—H14A118.0N2C—C14C—H14C118.3
C15A—C14A—H14A118.0C15C—C14C—H14C118.3
C14A—C15A—C16A119.7 (2)C14C—C15C—C16C119.0 (2)
C14A—C15A—C20A120.3 (2)C14C—C15C—C20C120.5 (2)
C16A—C15A—C20A120.0 (2)C16C—C15C—C20C120.5 (2)
C17A—C16A—C15A120.9 (3)C17C—C16C—C15C120.2 (2)
C17A—C16A—H16A119.6C17C—C16C—H16C119.9
C15A—C16A—H16A119.6C15C—C16C—H16C119.9
C16A—C17A—C18A120.5 (3)C16C—C17C—C18C120.3 (2)
C16A—C17A—H17A119.8C16C—C17C—H17C119.9
C18A—C17A—H17A119.8C18C—C17C—H17C119.9
C19A—C18A—C17A120.1 (3)C19C—C18C—C17C121.1 (2)
C19A—C18A—H18A120.0C19C—C18C—H18C119.4
C17A—C18A—H18A120.0C17C—C18C—H18C119.4
C18A—C19A—O4A120.7 (3)C18C—C19C—O4C120.7 (2)
C18A—C19A—C20A121.7 (3)C18C—C19C—C20C120.9 (2)
O4A—C19A—C20A117.6 (2)O4C—C19C—C20C118.4 (2)
O3A—C20A—C19A120.1 (2)O3C—C20C—C15C123.0 (2)
O3A—C20A—C15A123.1 (2)O3C—C20C—C19C120.0 (2)
C19A—C20A—C15A116.8 (2)C15C—C20C—C19C117.0 (2)
C11A—C21A—H21A109.5C11C—C21C—H21G109.5
C11A—C21A—H21B109.5C11C—C21C—H21H109.5
C11A—C21A—H21C109.5C11C—C21C—H21I109.5
C10A—C21E—H21M109.5C10C—C21G—H21P109.5
C10A—C21E—H21N109.5C10C—C21G—H21Q109.5
H21M—C21E—H21N109.5H21P—C21G—H21Q109.5
C10A—C21E—H21O109.5C10C—C21G—H21R109.5
H21M—C21E—H21O109.5H21P—C21G—H21R109.5
H21N—C21E—H21O109.5H21Q—C21G—H21R109.5
C2B—O1B—H1OB112.4 (19)C2D—O1D—H1OD108 (2)
C1B—O2B—H2OB107.6 (17)C1D—O2D—H2OD106.8 (18)
C19B—O4B—H4OB109 (2)C19D—O4D—H4OD110 (2)
C7B—N1B—C8B118.75 (19)C7D—N1D—C8D119.4 (2)
C14B—N2B—C13B127.8 (2)C14D—N2D—C13D127.0 (2)
C14B—N2B—H2NB109.9 (17)C14D—N2D—H2ND111.9 (16)
C13B—N2B—H2NB122.0 (17)C13D—N2D—H2ND120.9 (16)
O2B—C1B—C2B117.1 (2)O2D—C1D—C2D116.5 (2)
O2B—C1B—C6B122.6 (2)O2D—C1D—C6D123.0 (2)
C2B—C1B—C6B120.3 (2)C2D—C1D—C6D120.5 (2)
O1B—C2B—C3B119.1 (2)O1D—C2D—C3D119.3 (2)
O1B—C2B—C1B121.6 (2)O1D—C2D—C1D121.1 (2)
C3B—C2B—C1B119.3 (2)C3D—C2D—C1D119.6 (2)
C2B—C3B—C4B121.0 (2)C2D—C3D—C4D120.3 (2)
C2B—C3B—H3BA119.5C2D—C3D—H3DA119.9
C4B—C3B—H3BA119.5C4D—C3D—H3DA119.9
C5B—C4B—C3B120.1 (2)C5D—C4D—C3D120.3 (3)
C5B—C4B—H4BA120.0C5D—C4D—H4DA119.8
C3B—C4B—H4BA120.0C3D—C4D—H4DA119.8
C4B—C5B—C6B120.3 (2)C4D—C5D—C6D120.7 (2)
C4B—C5B—H5BA119.8C4D—C5D—H5DA119.7
C6B—C5B—H5BA119.8C6D—C5D—H5DA119.7
C1B—C6B—C5B119.0 (2)C1D—C6D—C5D118.6 (2)
C1B—C6B—C7B121.8 (2)C1D—C6D—C7D120.9 (2)
C5B—C6B—C7B119.2 (2)C5D—C6D—C7D120.4 (2)
N1B—C7B—C6B123.5 (2)N1D—C7D—C6D123.2 (2)
N1B—C7B—H7BA118.2N1D—C7D—H7DA118.4
C6B—C7B—H7BA118.2C6D—C7D—H7DA118.4
C9B—C8B—C13B118.6 (2)C9D—C8D—C13D117.9 (2)
C9B—C8B—N1B123.7 (2)C9D—C8D—N1D124.4 (2)
C13B—C8B—N1B117.6 (2)C13D—C8D—N1D117.7 (2)
C10B—C9B—C8B120.5 (2)C10D—C9D—C8D121.2 (3)
C10B—C9B—H9BA119.7C10D—C9D—H9DA119.4
C8B—C9B—H9BA119.7C8D—C9D—H9DA119.4
C9B—C10B—C11B121.3 (2)C9D—C10D—C11D121.4 (3)
C9B—C10B—C21F139.3 (11)C9D—C10D—C21H147 (3)
C11B—C10B—C21F94.8 (11)C11D—C10D—C21H91 (3)
C9B—C10B—H10B119.3C9D—C10D—H10D119.3
C11B—C10B—H10B119.3C11D—C10D—H10D119.3
C10B—C11B—C12B118.5 (2)C10D—C11D—C12D118.5 (2)
C10B—C11B—C21B121.0 (2)C10D—C11D—C21D121.3 (2)
C12B—C11B—C21B120.4 (2)C12D—C11D—C21D120.2 (3)
C10B—C11B—H11B120.7C10D—C11D—H11D120.8
C12B—C11B—H11B120.7C12D—C11D—H11D120.8
C13B—C12B—C11B120.4 (2)C13D—C12D—C11D120.2 (2)
C13B—C12B—H12B119.8C13D—C12D—H12D119.9
C11B—C12B—H12B119.8C11D—C12D—H12D119.9
C12B—C13B—C8B120.5 (2)C12D—C13D—C8D120.9 (2)
C12B—C13B—N2B122.2 (2)C12D—C13D—N2D121.9 (2)
C8B—C13B—N2B117.25 (19)C8D—C13D—N2D117.2 (2)
N2B—C14B—C15B122.7 (2)N2D—C14D—C15D124.1 (2)
N2B—C14B—H14B118.6N2D—C14D—H14D118.0
C15B—C14B—H14B118.6C15D—C14D—H14D118.0
C14B—C15B—C16B119.8 (2)C14D—C15D—C16D119.6 (2)
C14B—C15B—C20B119.8 (2)C14D—C15D—C20D120.4 (2)
C16B—C15B—C20B120.4 (2)C16D—C15D—C20D120.1 (2)
C17B—C16B—C15B120.5 (2)C17D—C16D—C15D120.4 (2)
C17B—C16B—H16B119.8C17D—C16D—H16D119.8
C15B—C16B—H16B119.8C15D—C16D—H16D119.8
C16B—C17B—C18B119.9 (2)C16D—C17D—C18D120.1 (2)
C16B—C17B—H17B120.0C16D—C17D—H17D120.0
C18B—C17B—H17B120.0C18D—C17D—H17D120.0
C19B—C18B—C17B121.1 (2)C19D—C18D—C17D121.3 (2)
C19B—C18B—H18B119.5C19D—C18D—H18D119.4
C17B—C18B—H18B119.5C17D—C18D—H18D119.4
C18B—C19B—O4B120.6 (2)C18D—C19D—O4D120.6 (2)
C18B—C19B—C20B121.5 (2)C18D—C19D—C20D121.1 (2)
O4B—C19B—C20B117.9 (2)O4D—C19D—C20D118.3 (2)
O3B—C20B—C19B119.8 (2)O3D—C20D—C15D123.1 (2)
O3B—C20B—C15B123.6 (2)O3D—C20D—C19D119.9 (2)
C19B—C20B—C15B116.7 (2)C15D—C20D—C19D117.0 (2)
C11B—C21B—H21D109.5C11D—C21D—H21J109.5
C11B—C21B—H21E109.5C11D—C21D—H21K109.5
C11B—C21B—H21F109.5C11D—C21D—H21L109.5
C10B—C21F—H21S109.5C10D—C21H—H21V109.5
C10B—C21F—H21T109.5C10D—C21H—H21W109.5
H21S—C21F—H21T109.5H21V—C21H—H21W109.5
C10B—C21F—H21U109.5C10D—C21H—H21X109.5
H21S—C21F—H21U109.5H21V—C21H—H21X109.5
H21T—C21F—H21U109.5H21W—C21H—H21X109.5
O2A—C1A—C2A—O1A0.2 (3)O2C—C1C—C2C—O1C1.9 (3)
C6A—C1A—C2A—O1A−179.2 (2)C6C—C1C—C2C—O1C−176.6 (2)
O2A—C1A—C2A—C3A178.5 (2)O2C—C1C—C2C—C3C−177.6 (2)
C6A—C1A—C2A—C3A−0.8 (4)C6C—C1C—C2C—C3C3.8 (4)
O1A—C2A—C3A—C4A178.4 (2)O1C—C2C—C3C—C4C178.3 (2)
C1A—C2A—C3A—C4A0.1 (4)C1C—C2C—C3C—C4C−2.1 (4)
C2A—C3A—C4A—C5A0.1 (4)C2C—C3C—C4C—C5C−0.7 (4)
C3A—C4A—C5A—C6A0.5 (4)C3C—C4C—C5C—C6C1.8 (4)
O2A—C1A—C6A—C5A−177.9 (2)O2C—C1C—C6C—C5C178.8 (2)
C2A—C1A—C6A—C5A1.4 (4)C2C—C1C—C6C—C5C−2.7 (3)
O2A—C1A—C6A—C7A2.9 (4)O2C—C1C—C6C—C7C−2.2 (4)
C2A—C1A—C6A—C7A−177.8 (2)C2C—C1C—C6C—C7C176.3 (2)
C4A—C5A—C6A—C1A−1.2 (4)C4C—C5C—C6C—C1C−0.1 (4)
C4A—C5A—C6A—C7A178.0 (3)C4C—C5C—C6C—C7C−179.1 (2)
C8A—N1A—C7A—C6A179.5 (2)C8C—N1C—C7C—C6C177.5 (2)
C1A—C6A—C7A—N1A−1.1 (4)C1C—C6C—C7C—N1C−1.2 (4)
C5A—C6A—C7A—N1A179.7 (2)C5C—C6C—C7C—N1C177.8 (2)
C7A—N1A—C8A—C13A−161.8 (2)C7C—N1C—C8C—C9C−35.0 (3)
C7A—N1A—C8A—C9A17.8 (4)C7C—N1C—C8C—C13C148.5 (2)
C13A—C8A—C9A—C10A1.6 (4)C13C—C8C—C9C—C10C−0.2 (4)
N1A—C8A—C9A—C10A−177.9 (2)N1C—C8C—C9C—C10C−176.6 (2)
C8A—C9A—C10A—C21E−174.3 (10)C8C—C9C—C10C—C11C1.4 (4)
C8A—C9A—C10A—C11A−1.1 (4)C8C—C9C—C10C—C21G−167.9 (6)
C21E—C10A—C11A—C12A174.3 (8)C9C—C10C—C11C—C12C−1.3 (4)
C9A—C10A—C11A—C12A−0.4 (4)C21G—C10C—C11C—C12C169.7 (6)
C21E—C10A—C11A—C21A−6.2 (8)C9C—C10C—C11C—C21C174.2 (3)
C9A—C10A—C11A—C21A179.1 (2)C21G—C10C—C11C—C21C−14.7 (6)
C10A—C11A—C12A—C13A1.4 (4)C10C—C11C—C12C—C13C0.0 (4)
C21A—C11A—C12A—C13A−178.1 (2)C21C—C11C—C12C—C13C−175.4 (3)
C9A—C8A—C13A—C12A−0.6 (4)C11C—C12C—C13C—C8C1.2 (4)
N1A—C8A—C13A—C12A178.9 (2)C11C—C12C—C13C—N2C−176.8 (2)
C9A—C8A—C13A—N2A179.1 (2)C9C—C8C—C13C—C12C−1.1 (3)
N1A—C8A—C13A—N2A−1.3 (3)N1C—C8C—C13C—C12C175.5 (2)
C11A—C12A—C13A—C8A−0.9 (4)C9C—C8C—C13C—N2C177.0 (2)
C11A—C12A—C13A—N2A179.4 (2)N1C—C8C—C13C—N2C−6.4 (3)
C14A—N2A—C13A—C8A164.4 (2)C14C—N2C—C13C—C12C10.5 (4)
C14A—N2A—C13A—C12A−15.9 (4)C14C—N2C—C13C—C8C−167.6 (2)
C13A—N2A—C14A—C15A179.0 (2)C13C—N2C—C14C—C15C179.7 (2)
N2A—C14A—C15A—C16A−177.8 (2)N2C—C14C—C15C—C16C178.5 (2)
N2A—C14A—C15A—C20A2.2 (4)N2C—C14C—C15C—C20C0.4 (4)
C14A—C15A—C16A—C17A−179.7 (2)C14C—C15C—C16C—C17C−177.3 (2)
C20A—C15A—C16A—C17A0.2 (4)C20C—C15C—C16C—C17C0.8 (4)
C15A—C16A—C17A—C18A1.2 (4)C15C—C16C—C17C—C18C0.4 (4)
C16A—C17A—C18A—C19A−0.7 (4)C16C—C17C—C18C—C19C−1.2 (4)
C17A—C18A—C19A—O4A179.1 (3)C17C—C18C—C19C—O4C179.5 (2)
C17A—C18A—C19A—C20A−1.3 (4)C17C—C18C—C19C—C20C0.8 (4)
C18A—C19A—C20A—O3A−177.4 (3)C14C—C15C—C20C—O3C−2.2 (4)
O4A—C19A—C20A—O3A2.2 (4)C16C—C15C—C20C—O3C179.6 (2)
C18A—C19A—C20A—C15A2.7 (4)C14C—C15C—C20C—C19C177.0 (2)
O4A—C19A—C20A—C15A−177.8 (2)C16C—C15C—C20C—C19C−1.1 (3)
C14A—C15A—C20A—O3A−2.1 (4)C18C—C19C—C20C—O3C179.6 (2)
C16A—C15A—C20A—O3A178.0 (2)O4C—C19C—C20C—O3C0.8 (3)
C14A—C15A—C20A—C19A177.9 (2)C18C—C19C—C20C—C15C0.3 (3)
C16A—C15A—C20A—C19A−2.1 (4)O4C—C19C—C20C—C15C−178.4 (2)
O2B—C1B—C2B—O1B0.9 (3)O2D—C1D—C2D—O1D0.0 (3)
C6B—C1B—C2B—O1B−179.0 (2)C6D—C1D—C2D—O1D−178.9 (2)
O2B—C1B—C2B—C3B−177.3 (2)O2D—C1D—C2D—C3D−179.1 (2)
C6B—C1B—C2B—C3B2.8 (3)C6D—C1D—C2D—C3D2.0 (3)
O1B—C2B—C3B—C4B179.6 (2)O1D—C2D—C3D—C4D−178.4 (2)
C1B—C2B—C3B—C4B−2.2 (4)C1D—C2D—C3D—C4D0.7 (4)
C2B—C3B—C4B—C5B0.2 (4)C2D—C3D—C4D—C5D−2.0 (4)
C3B—C4B—C5B—C6B1.2 (4)C3D—C4D—C5D—C6D0.6 (4)
O2B—C1B—C6B—C5B178.6 (2)O2D—C1D—C6D—C5D177.8 (2)
C2B—C1B—C6B—C5B−1.5 (3)C2D—C1D—C6D—C5D−3.4 (3)
O2B—C1B—C6B—C7B0.3 (4)O2D—C1D—C6D—C7D−6.5 (4)
C2B—C1B—C6B—C7B−179.8 (2)C2D—C1D—C6D—C7D172.2 (2)
C4B—C5B—C6B—C1B−0.5 (3)C4D—C5D—C6D—C1D2.1 (4)
C4B—C5B—C6B—C7B177.8 (2)C4D—C5D—C6D—C7D−173.6 (2)
C8B—N1B—C7B—C6B175.9 (2)C8D—N1D—C7D—C6D−176.6 (2)
C1B—C6B—C7B—N1B−0.4 (4)C1D—C6D—C7D—N1D−2.2 (4)
C5B—C6B—C7B—N1B−178.7 (2)C5D—C6D—C7D—N1D173.4 (2)
C7B—N1B—C8B—C9B−29.9 (3)C7D—N1D—C8D—C9D−37.0 (4)
C7B—N1B—C8B—C13B151.4 (2)C7D—N1D—C8D—C13D144.6 (2)
C13B—C8B—C9B—C10B−1.4 (3)C13D—C8D—C9D—C10D−1.7 (4)
N1B—C8B—C9B—C10B179.9 (2)N1D—C8D—C9D—C10D180.0 (2)
C8B—C9B—C10B—C11B1.8 (4)C8D—C9D—C10D—C11D0.4 (4)
C8B—C9B—C10B—C21F−147.3 (17)C8D—C9D—C10D—C21H−169 (5)
C9B—C10B—C11B—C12B−0.7 (4)C9D—C10D—C11D—C12D0.5 (4)
C21F—C10B—C11B—C12B159.6 (11)C21H—C10D—C11D—C12D175 (2)
C9B—C10B—C11B—C21B178.9 (2)C9D—C10D—C11D—C21D−178.8 (3)
C21F—C10B—C11B—C21B−20.8 (11)C21H—C10D—C11D—C21D−4(2)
C10B—C11B—C12B—C13B−0.6 (3)C10D—C11D—C12D—C13D0.0 (4)
C21B—C11B—C12B—C13B179.8 (2)C21D—C11D—C12D—C13D179.3 (2)
C11B—C12B—C13B—C8B0.9 (3)C11D—C12D—C13D—C8D−1.3 (4)
C11B—C12B—C13B—N2B−177.2 (2)C11D—C12D—C13D—N2D178.2 (2)
C9B—C8B—C13B—C12B0.1 (3)C9D—C8D—C13D—C12D2.2 (4)
N1B—C8B—C13B—C12B178.9 (2)N1D—C8D—C13D—C12D−179.4 (2)
C9B—C8B—C13B—N2B178.3 (2)C9D—C8D—C13D—N2D−177.4 (2)
N1B—C8B—C13B—N2B−2.9 (3)N1D—C8D—C13D—N2D1.1 (3)
C14B—N2B—C13B—C12B4.6 (4)C14D—N2D—C13D—C12D−3.8 (4)
C14B—N2B—C13B—C8B−173.6 (2)C14D—N2D—C13D—C8D175.8 (2)
C13B—N2B—C14B—C15B176.3 (2)C13D—N2D—C14D—C15D−177.5 (2)
N2B—C14B—C15B—C16B−179.0 (2)N2D—C14D—C15D—C16D−179.9 (2)
N2B—C14B—C15B—C20B−1.4 (3)N2D—C14D—C15D—C20D−0.5 (4)
C14B—C15B—C16B—C17B177.6 (2)C14D—C15D—C16D—C17D179.2 (2)
C20B—C15B—C16B—C17B0.0 (4)C20D—C15D—C16D—C17D−0.2 (4)
C15B—C16B—C17B—C18B0.4 (4)C15D—C16D—C17D—C18D0.5 (4)
C16B—C17B—C18B—C19B−0.5 (4)C16D—C17D—C18D—C19D0.2 (4)
C17B—C18B—C19B—O4B−179.6 (2)C17D—C18D—C19D—O4D179.2 (2)
C17B—C18B—C19B—C20B0.2 (4)C17D—C18D—C19D—C20D−1.2 (4)
C18B—C19B—C20B—O3B−178.7 (2)C14D—C15D—C20D—O3D−0.2 (4)
O4B—C19B—C20B—O3B1.1 (3)C16D—C15D—C20D—O3D179.2 (2)
C18B—C19B—C20B—C15B0.2 (3)C14D—C15D—C20D—C19D179.8 (2)
O4B—C19B—C20B—C15B180.0 (2)C16D—C15D—C20D—C19D−0.8 (3)
C14B—C15B—C20B—O3B0.9 (3)C18D—C19D—C20D—O3D−178.5 (2)
C16B—C15B—C20B—O3B178.5 (2)O4D—C19D—C20D—O3D1.1 (3)
C14B—C15B—C20B—C19B−177.9 (2)C18D—C19D—C20D—C15D1.5 (3)
C16B—C15B—C20B—C19B−0.3 (3)O4D—C19D—C20D—C15D−178.9 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···N1A0.92 (3)1.86 (3)2.686 (3)149 (3)
O2B—H2OB···N1B0.96 (3)1.82 (3)2.671 (2)146 (2)
O2C—H2OC···N1C0.99 (3)1.72 (3)2.634 (3)151 (3)
O2D—H2OD···N1D0.95 (3)1.81 (3)2.652 (3)147 (3)
N2A—H2NA···O3A0.92 (3)1.86 (3)2.631 (3)140 (2)
N2B—H2NB···O3B1.03 (3)1.70 (3)2.596 (2)144 (3)
N2C—H2NC···O3C0.95 (3)1.83 (2)2.620 (3)139 (2)
N2D—H2ND···O3D0.97 (3)1.80 (3)2.624 (2)140 (2)
O1C—H1OC···O3D0.88 (3)1.91 (4)2.734 (3)155 (3)
O1D—H1OD···O3C0.91 (3)1.93 (3)2.724 (2)146 (3)
O4C—H4OC···O2D0.88 (4)2.48 (4)3.079 (3)126 (3)
O4C—H4OC···O3D0.88 (4)2.31 (4)3.026 (2)138 (3)
O4D—H4OD···O2C0.85 (3)2.34 (3)2.942 (2)129 (3)
O4D—H4OD···O3C0.85 (3)2.29 (3)2.943 (3)134 (3)
O1A—H1OA···O3Bi0.89 (3)1.88 (3)2.732 (2)160 (3)
O1B—H1OB···O3Aii0.85 (3)2.01 (3)2.809 (3)157 (3)
O4A—H4OA···O2Bi0.81 (4)2.25 (4)2.929 (3)142 (4)
O4B—H4OB···O2Aii0.91 (4)2.33 (3)3.021 (3)133 (3)
O4B—H4OB···O3Aii0.91 (4)2.53 (4)3.231 (3)134 (3)
C5B—H5BA···O1Diii0.932.523.372 (3)152
C7B—H7BA···O1Diii0.932.573.416 (3)151
C14A—H14A···O4Div0.932.363.281 (3)170
C14B—H14B···O1Civ0.932.403.260 (3)154
C14C—H14C···O4Bv0.932.463.323 (3)154
C10D—H10D···Cg1vi0.932.973.623 (3)128
C9A—H9AA···Cg2vii0.932.973.716 (3)138
C9C—H9CA···Cg30.932.653.480 (3)148
C21C—H21I···Cg4v0.962.953.696 (4)136
C4B—H4BA···Cg5viii0.932.833.573 (3)138
C17D—H17D···Cg6ix0.932.693.450 (3)139
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) x, −y+1/2, z−3/2; (vii) −x+1, −y+1, −z+2; (viii) x, −y+1/2, z−1/2; (ix) −x+1, y−1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
O3A—C20A1.289 (3)O3C—C20C1.299 (3)
N2A—C14A1.309 (3)N2C—C14C1.307 (3)
C14A—C15A1.404 (3)C14C—C15C1.407 (3)
O3B—C20B1.292 (3)O3D—C20D1.295 (3)
N2B—C14B1.316 (3)N2D—C14D1.313 (3)
C14B—C15B1.409 (3)C14D—C15D1.397 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···N1A0.92 (3)1.86 (3)2.686 (3)149 (3)
O2B—H2OB···N1B0.96 (3)1.82 (3)2.671 (2)146 (2)
O2C—H2OC···N1C0.99 (3)1.72 (3)2.634 (3)151 (3)
O2D—H2OD···N1D0.95 (3)1.81 (3)2.652 (3)147 (3)
N2A—H2NA···O3A0.92 (3)1.86 (3)2.631 (3)140 (2)
N2B—H2NB···O3B1.03 (3)1.70 (3)2.596 (2)144 (3)
N2C—H2NC···O3C0.95 (3)1.83 (2)2.620 (3)139 (2)
N2D—H2ND···O3D0.97 (3)1.80 (3)2.624 (2)140 (2)
O1C—H1OC···O3D0.88 (3)1.91 (4)2.734 (3)155 (3)
O1D—H1OD···O3C0.91 (3)1.93 (3)2.724 (2)146 (3)
O4C—H4OC···O2D0.88 (4)2.48 (4)3.079 (3)126 (3)
O4C—H4OC···O3D0.88 (4)2.31 (4)3.026 (2)138 (3)
O4D—H4OD···O2C0.85 (3)2.34 (3)2.942 (2)129 (3)
O4D—H4OD···O3C0.85 (3)2.29 (3)2.943 (3)134 (3)
O1A—H1OA···O3Bi0.89 (3)1.88 (3)2.732 (2)160 (3)
O1B—H1OB···O3Aii0.85 (3)2.01 (3)2.809 (3)157 (3)
O4A—H4OA···O2Bi0.81 (4)2.25 (4)2.929 (3)142 (4)
O4B—H4OB···O2Aii0.91 (4)2.33 (3)3.021 (3)133 (3)
O4B—H4OB···O3Aii0.91 (4)2.53 (4)3.231 (3)134 (3)
C5B—H5BA···O1Diii0.932.523.372 (3)152
C7B—H7BA···O1Diii0.932.573.416 (3)151
C14A—H14A···O4Div0.932.363.281 (3)170
C14B—H14B···O1Civ0.932.403.260 (3)154
C14C—H14C···O4Bv0.932.463.323 (3)154
C10D—H10D···Cg1vi0.932.973.623 (3)128
C9A—H9AA···Cg2vii0.932.973.716 (3)138
C9C—H9CA···Cg30.932.653.480 (3)148
C21C—H21I···Cg4v0.962.953.696 (4)136
C4B—H4BA···Cg5viii0.932.833.573 (3)138
C17D—H17D···Cg6ix0.932.693.450 (3)139
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) x, −y+1/2, z−3/2; (vii) −x+1, −y+1, −z+2; (viii) x, −y+1/2, z−1/2; (ix) −x+1, y−1/2, −z+1/2.
Acknowledgements top

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia (USM) for the E-Science Fund and RU research grants (Nos. PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. HKF and CSY thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). CSY thanks the Malaysian Government and USM for the award of the post of Research Officer under the Science Fund (grant No. 305/PFIZIK/613312).

references
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