supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, m1436-m1437    [ doi:10.1107/S1600536808033321 ]

Octaakis(4-aminopyridine)-1[kappa]4N1,2[kappa]4N1-aqua-2[kappa]O-[mu]-carbonato-1:2[kappa]3O,O':O''-dinickel(II) dichloride pentahydrate

H.-K. Fun, A. Sinthiya, S. R. Jebas, B. Ravindran Durai Nayagam and S. Alfred Cecil Raj

Abstract top

In the title compound, [Ni2(CO3)(C5H6N2)8(H2O)]Cl2·5H2O, one of the the NiII ions is six-coordinated in a distorted octahedral geometry, with the equatorial plane defined by four pyridine N atoms from four aminopyridine ligands, the axial positions being occupied by one water O and a carbonate O atom. The other NiII ion is also six-coordinated, by four other pyridine N atoms from four other aminopyridine ligands and two carbonate O atoms to complete a distorted octahedral geometry. In the crystal structure, molecules are linked into an infinite three-dimensional network by O-H...O, N-H...Cl, N-H...O, O-H...N, C-H...O, C-H...N and C/N-H...[pi] interactions involving the pyridine rings.

Comment top

4-Aminopyridine (Fampridine) is used clinically in Lambert-Eaton myasthenic syndrome and multiple sclerosis because by blocking the potassium channels it prolongs action potentials thereby increasing transmitter release at the neuromuscular junction (Judge & Bever, 2006; Schwid et al.,1997; Strupp et al., 2004). As a part of our investigation of the binding modes of 4-aminopyridine with the metals, we report here the crystal structure of the title compound, (I).

In the asymmetric unit of the title compound, both of the NiII ions have distorted octahedral geometry. The equatorial plane in Ni1 is formed by four N pyridine atoms from four aminopyridine ligands, the axial positions being occupied by one water oxygen atom and a carbonate oxygen atom. In Ni2, the equatorial plane is formed by four other pyridine N atoms from four other aminopyridine ligands, the axial positions being occupied by two carbonate oxygen atoms. Two chlorine and five other water molecules are also present within the asymmetric unit (Fig. 1). Two of these water molecules are disordered with the fixed occupany of 0.5:0.5. The bond lengths and angles are found to have normal values (Jebas et al., 2007; Allen et al., 1987).

The crystal packing is consolidated by intramolecular and intermolecular O—H···O, N—H···Cl, N—H···O, O—H···N, C—H···O and C—H···N hydrogen bonds to form an infinite three dimensional network. (C/N—H···π) interactions involving the pyridine rings are also observed.

Related literature top

For related literature on 4-aminopyridine, see: Judge & Bever (2006); Schwid et al. (1997); Strupp et al. (2004). For bond-length data, see: Allen et al. (1987); Jebas et al. (2007).

Experimental top

A solution of 4-aminopyridine (0.376 g) in methanol (20 ml) was added to a solution of NiCl2.6H2O (.237 g) in methanol (20 ml) and the mixture was stirred at a temperature of 303 K for 12 h. The clear blue solution obtained was filtered and allowed to evaporate slowly. Blue crystals of the title compound were obtained after two weeks.

Refinement top

All the hydrogen atoms were positioned geometrically [C—H=0.93 Å; N—H=0.86 Å and O—H=0.85 Å] and refined using a riding model, with Uiso(H)=1.2–1.5Uequ(C,N and O). The two disordered water molecules are refined with the fixed site occupancy of 0.5:0.5.

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, 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 along the c axis.
Octaakis(4-aminopyridine)-1κ4N1,2κ4N1-aqua-2κO-µ-carbonato- 1:2κ3O,O':O''-dinickel(II) dichloride pentahydrate top
Crystal data top
[Ni2(CO3)(C5H6N2)8(H2O)]Cl2·5H2OZ = 2
Mr = 1109.37F(000) = 1160
Triclinic, P1Dx = 1.426 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.8877 (3) ÅCell parameters from 8874 reflections
b = 14.7920 (3) Åθ = 2.5–31.9°
c = 15.0510 (3) ŵ = 0.90 mm−1
α = 82.797 (1)°T = 100 K
β = 68.748 (1)°Block, blue
γ = 75.191 (1)°0.73 × 0.25 × 0.21 mm
V = 2583.59 (9) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		13659 independent reflections
Radiation source: fine-focus sealed tube10282 reflections with I > 2σ(I)
graphiteRint = 0.046
φ and ω scansθmax = 29.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −17→17
Tmin = 0.560, Tmax = 0.834k = −20→20
42253 measured reflectionsl = −20→20
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0775P)2 + 7.7222P]
where P = (Fo2 + 2Fc2)/3
13659 reflections(Δ/σ)max < 0.001
647 parametersΔρmax = 2.22 e Å−3
0 restraintsΔρmin = −1.94 e Å−3
Crystal data top
[Ni2(CO3)(C5H6N2)8(H2O)]Cl2·5H2Oγ = 75.191 (1)°
Mr = 1109.37V = 2583.59 (9) Å3
Triclinic, P1Z = 2
a = 12.8877 (3) ÅMo Kα radiation
b = 14.7920 (3) ŵ = 0.90 mm−1
c = 15.0510 (3) ÅT = 100 K
α = 82.797 (1)°0.73 × 0.25 × 0.21 mm
β = 68.748 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		13659 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		10282 reflections with I > 2σ(I)
Tmin = 0.560, Tmax = 0.834Rint = 0.046
42253 measured reflectionsθmax = 29.0°
Refinement top
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.180Δρmax = 2.22 e Å−3
S = 1.04Δρmin = −1.94 e Å−3
13659 reflectionsAbsolute structure: ?
647 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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

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 > 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)
C10.5271 (3)0.9042 (3)0.2051 (3)0.0233 (7)
H10.46000.88950.20800.028*
C20.5181 (3)0.9898 (2)0.2360 (3)0.0231 (7)
H20.44711.03080.25860.028*
C30.6164 (3)1.0154 (3)0.2336 (3)0.0309 (9)
C40.7188 (3)0.9500 (3)0.1959 (4)0.0396 (11)
H40.78740.96390.19020.048*
C50.7195 (3)0.8659 (3)0.1673 (3)0.0298 (8)
H50.78960.82380.14380.036*
C60.8176 (3)0.6901 (3)−0.0318 (3)0.0252 (7)
H60.75480.7170−0.05040.030*
C70.9231 (3)0.6713 (3)−0.1012 (3)0.0285 (8)
H70.93030.6853−0.16480.034*
C81.0202 (3)0.6312 (3)−0.0768 (3)0.0249 (7)
C91.0021 (3)0.6128 (3)0.0207 (3)0.0240 (7)
H91.06350.58650.04130.029*
C100.8929 (3)0.6341 (2)0.0853 (3)0.0213 (7)
H100.88330.62130.14960.026*
C110.7216 (3)0.5782 (2)0.2989 (2)0.0210 (7)
H110.74800.53530.25100.025*
C120.7460 (3)0.5495 (3)0.3803 (3)0.0237 (7)
H120.78650.48870.38690.028*
C130.7097 (3)0.6124 (3)0.4542 (3)0.0248 (7)
C140.6474 (4)0.7018 (3)0.4381 (3)0.0272 (8)
H140.62080.74640.48440.033*
C150.6256 (3)0.7235 (3)0.3543 (3)0.0236 (7)
H150.58300.78300.34630.028*
C160.5630 (3)0.5103 (2)0.2170 (2)0.0206 (7)
H160.54480.53170.27760.025*
C170.5325 (3)0.4300 (3)0.2104 (2)0.0215 (7)
H170.49790.39700.26540.026*
C180.5538 (3)0.3976 (2)0.1201 (2)0.0193 (6)
C190.6132 (3)0.4486 (3)0.0408 (2)0.0219 (7)
H190.63250.4291−0.02070.026*
C200.6421 (3)0.5268 (2)0.0552 (2)0.0208 (7)
H200.68160.55900.00170.025*
C210.2826 (3)0.9510 (3)0.0819 (2)0.0215 (7)
H210.29530.91360.03200.026*
C220.3296 (3)1.0281 (2)0.0609 (2)0.0218 (7)
H220.37101.0426−0.00180.026*
C230.3147 (3)1.0847 (2)0.1346 (3)0.0205 (7)
C240.2439 (3)1.0618 (2)0.2266 (3)0.0224 (7)
H240.22691.09930.27750.027*
C250.2001 (3)0.9832 (2)0.2403 (3)0.0212 (7)
H250.15460.96900.30170.025*
C260.1996 (3)0.7820 (3)−0.0090 (3)0.0255 (7)
H260.27260.7480−0.01310.031*
C270.1732 (4)0.7973 (3)−0.0911 (3)0.0306 (8)
H270.22780.7743−0.14830.037*
C280.0646 (3)0.8472 (3)−0.0888 (3)0.0253 (7)
C29−0.0111 (3)0.8795 (3)0.0001 (3)0.0280 (8)
H29−0.08450.91400.00620.034*
C300.0226 (3)0.8603 (3)0.0787 (3)0.0278 (8)
H30−0.03070.88170.13710.033*
C31−0.0446 (3)0.9253 (3)0.3014 (3)0.0237 (7)
H31−0.01750.96590.25060.028*
C32−0.1482 (3)0.9588 (3)0.3702 (3)0.0281 (8)
H32−0.18901.01980.36510.034*
C33−0.1919 (3)0.8998 (3)0.4486 (3)0.0269 (8)
C34−0.1233 (3)0.8102 (3)0.4509 (3)0.0280 (8)
H34−0.14710.76840.50150.034*
C35−0.0205 (3)0.7837 (3)0.3785 (3)0.0231 (7)
H350.02370.72390.38270.028*
C360.0675 (3)0.6296 (3)0.2273 (3)0.0229 (7)
H360.00800.67640.21840.028*
C370.0479 (3)0.5409 (3)0.2534 (3)0.0256 (8)
H37−0.02240.52910.26120.031*
C380.1362 (3)0.4684 (2)0.2680 (2)0.0216 (7)
C390.2416 (3)0.4919 (2)0.2481 (2)0.0210 (7)
H390.30460.44570.25130.025*
C400.2520 (3)0.5823 (2)0.2239 (2)0.0198 (6)
H400.32210.59600.21380.024*
C410.4459 (3)0.7377 (2)0.1216 (2)0.0170 (6)
N10.6252 (2)0.8396 (2)0.1708 (2)0.0184 (6)
N20.6106 (3)1.0977 (3)0.2669 (4)0.0489 (11)
H2A0.67191.11190.26530.059*
H2B0.54551.13610.28960.059*
N30.7989 (2)0.6720 (2)0.0625 (2)0.0191 (6)
N41.1259 (3)0.6082 (3)−0.1450 (2)0.0350 (8)
H4A1.13380.6183−0.20430.042*
H4B1.18470.5835−0.12860.042*
N50.6625 (3)0.6635 (2)0.2825 (2)0.0199 (6)
N60.7329 (4)0.5873 (3)0.5356 (2)0.0377 (9)
H6A0.70920.62680.58000.045*
H6B0.77130.53190.54310.045*
N70.6177 (2)0.5606 (2)0.1413 (2)0.0190 (6)
N80.5179 (3)0.3224 (2)0.1102 (2)0.0236 (6)
H8A0.48110.29310.15990.028*
H8B0.53200.30390.05420.028*
N90.2186 (2)0.9262 (2)0.1713 (2)0.0196 (6)
N100.3662 (3)1.1568 (2)0.1190 (2)0.0251 (6)
H10A0.40981.16910.06250.030*
H10B0.35551.19030.16560.030*
N110.1267 (2)0.8131 (2)0.0769 (2)0.0195 (6)
N120.0350 (3)0.8655 (3)−0.1682 (3)0.0366 (8)
H12A−0.03210.8979−0.16450.044*
H12B0.08330.8448−0.22220.044*
N130.0203 (2)0.8390 (2)0.3017 (2)0.0197 (6)
N14−0.2945 (3)0.9289 (3)0.5175 (3)0.0412 (10)
H14A−0.31950.89170.56480.049*
H14B−0.33460.98460.51390.049*
N150.1660 (2)0.6529 (2)0.2140 (2)0.0193 (6)
N160.1213 (3)0.3815 (2)0.2988 (3)0.0299 (7)
H16A0.17700.33880.30670.036*
H16B0.05600.36870.31060.036*
Ni10.62871 (4)0.69875 (3)0.15544 (3)0.01710 (11)
Ni20.18322 (4)0.79166 (3)0.19613 (3)0.01683 (11)
Cl10.35627 (8)0.23887 (6)0.31722 (6)0.02547 (19)
Cl20.90118 (15)0.27828 (13)0.34939 (11)0.0716 (5)
O10.3536 (2)0.74562 (17)0.10538 (17)0.0188 (5)
O1W0.2427 (2)0.76585 (17)0.31497 (17)0.0207 (5)
H1W10.31000.75070.27480.031*
H2W10.22490.71600.34440.031*
O20.5421 (2)0.73727 (17)0.05345 (16)0.0181 (5)
O30.4495 (2)0.72752 (17)0.20747 (17)0.0191 (5)
O2W0.7793 (4)0.3796 (2)0.5453 (2)0.0571 (11)
H1W20.84310.34880.50960.086*
H2W20.73260.34400.56300.086*
O3W0.5677 (5)0.4100 (4)0.5178 (5)0.111 (2)
H1W30.51550.38980.56290.167*
H2W30.55340.41060.46660.167*
O4W0.7123 (7)0.2467 (3)0.3499 (3)0.123 (3)
H1W40.76850.26670.34960.185*
H2W40.68490.28030.30990.185*
O5WA0.1451 (6)0.8802 (4)0.4730 (4)0.0363 (14)0.50
H1W50.13030.87120.42460.054*0.50
H2W50.14470.83010.50760.054*0.50
O5WB0.7622 (7)0.1175 (5)0.5465 (5)0.0505 (18)0.50
H1WA0.72730.14820.59690.076*0.50
H2WB0.74780.06350.55790.076*0.50
O6WA0.6332 (5)0.1318 (4)0.5175 (4)0.0502 (18)0.50
H1W60.56290.13100.53500.075*0.50
H2W60.64780.16880.46890.075*0.50
O6WB0.9981 (5)0.9408 (4)0.5318 (4)0.0533 (18)0.50
H1WC1.00980.93620.58440.080*0.50
H2WD0.94770.91040.53860.080*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0196 (17)0.0245 (17)0.0278 (18)−0.0055 (14)−0.0111 (14)0.0014 (14)
C20.0176 (16)0.0197 (16)0.0283 (18)0.0018 (13)−0.0076 (14)−0.0015 (14)
C30.0219 (18)0.0227 (18)0.047 (2)−0.0037 (15)−0.0104 (17)−0.0039 (17)
C40.0177 (18)0.030 (2)0.072 (3)−0.0066 (16)−0.012 (2)−0.011 (2)
C50.0179 (17)0.0234 (18)0.045 (2)−0.0036 (14)−0.0072 (16)−0.0042 (16)
C60.0218 (17)0.0298 (19)0.0230 (17)−0.0004 (14)−0.0094 (14)−0.0033 (14)
C70.030 (2)0.033 (2)0.0204 (17)−0.0034 (16)−0.0081 (15)−0.0031 (15)
C80.0250 (18)0.0212 (17)0.0261 (18)−0.0020 (14)−0.0068 (15)−0.0050 (14)
C90.0190 (16)0.0258 (18)0.0267 (18)−0.0005 (14)−0.0103 (14)−0.0017 (14)
C100.0211 (17)0.0226 (17)0.0226 (16)−0.0058 (13)−0.0106 (14)0.0014 (13)
C110.0230 (17)0.0210 (16)0.0202 (16)−0.0067 (13)−0.0083 (14)0.0009 (13)
C120.0259 (18)0.0212 (17)0.0254 (17)−0.0065 (14)−0.0111 (15)0.0037 (14)
C130.032 (2)0.0245 (18)0.0209 (17)−0.0072 (15)−0.0125 (15)0.0017 (14)
C140.038 (2)0.0227 (18)0.0235 (17)−0.0071 (16)−0.0121 (16)−0.0028 (14)
C150.0266 (18)0.0218 (17)0.0217 (17)−0.0045 (14)−0.0086 (14)0.0010 (13)
C160.0215 (16)0.0221 (16)0.0202 (16)−0.0058 (13)−0.0092 (13)0.0000 (13)
C170.0204 (16)0.0242 (17)0.0201 (16)−0.0074 (14)−0.0067 (13)0.0027 (13)
C180.0156 (15)0.0193 (16)0.0222 (16)−0.0029 (12)−0.0065 (13)−0.0007 (13)
C190.0229 (17)0.0245 (17)0.0182 (16)−0.0047 (14)−0.0072 (13)−0.0017 (13)
C200.0212 (17)0.0215 (16)0.0182 (15)−0.0040 (13)−0.0062 (13)0.0018 (13)
C210.0224 (17)0.0237 (17)0.0195 (16)−0.0057 (14)−0.0092 (14)0.0028 (13)
C220.0244 (17)0.0221 (17)0.0195 (16)−0.0076 (14)−0.0085 (14)0.0044 (13)
C230.0164 (15)0.0187 (16)0.0259 (17)−0.0036 (12)−0.0090 (13)0.0057 (13)
C240.0248 (18)0.0203 (16)0.0213 (16)−0.0052 (14)−0.0069 (14)−0.0005 (13)
C250.0195 (16)0.0213 (16)0.0201 (16)−0.0037 (13)−0.0048 (13)0.0011 (13)
C260.0212 (17)0.0283 (19)0.0229 (17)−0.0011 (14)−0.0065 (14)0.0007 (14)
C270.031 (2)0.033 (2)0.0214 (18)−0.0005 (16)−0.0064 (16)−0.0007 (15)
C280.0305 (19)0.0231 (17)0.0257 (18)−0.0097 (15)−0.0140 (15)0.0081 (14)
C290.0231 (18)0.0297 (19)0.033 (2)−0.0033 (15)−0.0147 (16)0.0037 (15)
C300.0171 (17)0.036 (2)0.0280 (19)−0.0014 (15)−0.0067 (15)−0.0048 (16)
C310.0238 (18)0.0218 (17)0.0225 (17)−0.0061 (14)−0.0041 (14)0.0002 (13)
C320.0257 (19)0.0174 (16)0.033 (2)−0.0033 (14)−0.0025 (16)0.0018 (14)
C330.0248 (18)0.0238 (18)0.0266 (18)−0.0055 (15)−0.0019 (15)−0.0024 (14)
C340.0242 (18)0.0267 (19)0.0263 (18)−0.0057 (15)−0.0025 (15)0.0042 (15)
C350.0222 (17)0.0223 (17)0.0222 (17)−0.0043 (14)−0.0056 (14)0.0005 (13)
C360.0186 (16)0.0242 (17)0.0295 (18)−0.0047 (13)−0.0135 (14)0.0021 (14)
C370.0213 (17)0.0260 (18)0.035 (2)−0.0089 (14)−0.0152 (16)0.0023 (15)
C380.0250 (18)0.0220 (17)0.0220 (16)−0.0085 (14)−0.0114 (14)0.0011 (13)
C390.0195 (16)0.0200 (16)0.0227 (16)−0.0016 (13)−0.0086 (14)0.0001 (13)
C400.0174 (16)0.0207 (16)0.0219 (16)−0.0037 (13)−0.0076 (13)−0.0016 (13)
C410.0149 (15)0.0159 (15)0.0191 (15)−0.0019 (12)−0.0059 (12)0.0011 (12)
N10.0179 (13)0.0181 (13)0.0195 (13)−0.0040 (11)−0.0075 (11)0.0010 (11)
N20.0255 (18)0.0280 (19)0.097 (4)−0.0023 (15)−0.022 (2)−0.023 (2)
N30.0148 (13)0.0187 (14)0.0227 (14)−0.0027 (11)−0.0060 (11)−0.0003 (11)
N40.0270 (17)0.042 (2)0.0265 (17)0.0020 (15)−0.0035 (14)−0.0072 (15)
N50.0196 (14)0.0217 (14)0.0200 (14)−0.0053 (11)−0.0087 (11)0.0002 (11)
N60.067 (3)0.0260 (17)0.0275 (17)−0.0062 (17)−0.0294 (18)0.0026 (14)
N70.0192 (14)0.0194 (14)0.0190 (13)−0.0041 (11)−0.0077 (11)0.0002 (11)
N80.0257 (15)0.0251 (15)0.0216 (14)−0.0123 (13)−0.0045 (12)−0.0037 (12)
N90.0174 (13)0.0190 (14)0.0210 (14)−0.0054 (11)−0.0052 (11)0.0031 (11)
N100.0316 (17)0.0232 (15)0.0239 (15)−0.0142 (13)−0.0099 (13)0.0046 (12)
N110.0181 (14)0.0198 (14)0.0201 (14)−0.0039 (11)−0.0070 (11)0.0016 (11)
N120.045 (2)0.038 (2)0.0289 (18)−0.0063 (17)−0.0200 (16)0.0085 (15)
N130.0161 (13)0.0213 (14)0.0208 (14)−0.0052 (11)−0.0053 (11)0.0003 (11)
N140.0302 (19)0.0288 (18)0.039 (2)−0.0005 (15)0.0126 (16)0.0033 (15)
N150.0206 (14)0.0163 (13)0.0209 (14)−0.0040 (11)−0.0080 (11)0.0019 (11)
N160.0323 (18)0.0213 (15)0.044 (2)−0.0120 (13)−0.0215 (16)0.0086 (14)
Ni10.0158 (2)0.0189 (2)0.0175 (2)−0.00417 (16)−0.00708 (16)0.00114 (16)
Ni20.0153 (2)0.0167 (2)0.0176 (2)−0.00361 (16)−0.00508 (16)0.00077 (15)
Cl10.0284 (4)0.0199 (4)0.0233 (4)−0.0037 (3)−0.0047 (3)0.0000 (3)
Cl20.0797 (11)0.0871 (11)0.0457 (7)−0.0515 (9)0.0068 (7)−0.0139 (7)
O10.0166 (11)0.0220 (12)0.0186 (11)−0.0053 (9)−0.0062 (9)−0.0016 (9)
O1W0.0202 (12)0.0235 (12)0.0167 (11)−0.0054 (10)−0.0055 (9)0.0028 (9)
O20.0148 (11)0.0217 (12)0.0177 (11)−0.0044 (9)−0.0064 (9)0.0021 (9)
O30.0168 (11)0.0235 (12)0.0182 (11)−0.0058 (9)−0.0071 (9)0.0013 (9)
O2W0.096 (3)0.0306 (17)0.0274 (16)−0.0150 (18)−0.0023 (18)0.0028 (13)
O3W0.080 (4)0.072 (3)0.157 (6)−0.045 (3)−0.002 (4)0.025 (4)
O4W0.284 (9)0.069 (3)0.034 (2)−0.087 (4)−0.043 (4)0.000 (2)
O5WA0.058 (4)0.035 (3)0.021 (3)−0.018 (3)−0.013 (3)0.000 (2)
O5WB0.057 (5)0.045 (4)0.047 (4)−0.015 (4)−0.006 (4)−0.024 (3)
O6WA0.041 (4)0.034 (3)0.060 (5)−0.006 (3)−0.003 (3)0.003 (3)
O6WB0.059 (5)0.059 (5)0.055 (4)−0.023 (4)−0.028 (4)−0.003 (4)
Geometric parameters (Å, °) top
C1—N11.346 (5)C32—C331.407 (5)
C1—C21.366 (5)C32—H320.9300
C1—H10.9300C33—N141.355 (5)
C2—C31.400 (5)C33—C341.398 (5)
C2—H20.9300C34—C351.376 (5)
C3—N21.348 (5)C34—H340.9300
C3—C41.392 (6)C35—N131.350 (4)
C4—C51.365 (6)C35—H350.9300
C4—H40.9300C36—N151.339 (4)
C5—N11.349 (5)C36—C371.380 (5)
C5—H50.9300C36—H360.9300
C6—N31.354 (5)C37—C381.411 (5)
C6—C71.367 (5)C37—H370.9300
C6—H60.9300C38—N161.347 (4)
C7—C81.396 (5)C38—C391.406 (5)
C7—H70.9300C39—C401.370 (5)
C8—N41.364 (5)C39—H390.9300
C8—C91.402 (5)C40—N151.353 (4)
C9—C101.372 (5)C40—H400.9300
C9—H90.9300C41—O11.273 (4)
C10—N31.344 (4)C41—O21.291 (4)
C10—H100.9300C41—O31.298 (4)
C11—N51.342 (5)C41—Ni12.498 (3)
C11—C121.365 (5)N1—Ni12.112 (3)
C11—H110.9300N2—H2A0.8600
C12—C131.408 (5)N2—H2B0.8600
C12—H120.9300N3—Ni12.096 (3)
C13—N61.350 (5)N4—H4A0.8600
C13—C141.404 (5)N4—H4B0.8600
C14—C151.372 (5)N5—Ni12.087 (3)
C14—H140.9300N6—H6A0.8600
C15—N51.354 (5)N6—H6B0.8600
C15—H150.9300N7—Ni12.126 (3)
C16—N71.350 (4)N8—H8A0.8600
C16—C171.368 (5)N8—H8B0.8600
C16—H160.9300N9—Ni22.113 (3)
C17—C181.407 (5)N10—H10A0.8600
C17—H170.9300N10—H10B0.8600
C18—N81.352 (4)N11—Ni22.131 (3)
C18—C191.409 (5)N12—H12A0.8600
C19—C201.367 (5)N12—H12B0.8600
C19—H190.9300N13—Ni22.129 (3)
C20—N71.347 (4)N14—H14A0.8600
C20—H200.9300N14—H14B0.8600
C21—N91.361 (4)N15—Ni22.095 (3)
C21—C221.375 (5)N16—H16A0.8600
C21—H210.9300N16—H16B0.8600
C22—C231.401 (5)Ni1—O32.097 (2)
C22—H220.9300Ni1—O22.150 (2)
C23—N101.348 (4)Ni2—O12.109 (2)
C23—C241.411 (5)Ni2—O1W2.146 (2)
C24—C251.379 (5)Cl2—H1W41.7605
C24—H240.9300O1W—H1W10.8500
C25—N91.335 (5)O1W—H2W10.8502
C25—H250.9300O2W—H1W20.8501
C26—N111.347 (5)O2W—H2W20.8491
C26—C271.374 (5)O3W—H1W30.8503
C26—H260.9300O3W—H2W30.8526
C27—C281.396 (6)O4W—H1W40.8481
C27—H270.9300O4W—H2W40.8504
C28—N121.358 (5)O5WA—H1W50.8501
C28—C291.395 (6)O5WA—H2W50.8501
C29—C301.376 (5)O5WB—H1WA0.8468
C29—H290.9300O5WB—H2WB0.8478
C30—N111.338 (5)O6WA—H1W60.8500
C30—H300.9300O6WA—H2W60.8500
C31—N131.335 (5)O6WB—H1WC0.8498
C31—C321.375 (5)O6WB—H2WD0.8500
C31—H310.9300
N1—C1—C2125.3 (3)N16—C38—C37122.4 (3)
N1—C1—H1117.4C39—C38—C37116.0 (3)
C2—C1—H1117.4C40—C39—C38120.4 (3)
C1—C2—C3119.7 (3)C40—C39—H39119.8
C1—C2—H2120.2C38—C39—H39119.8
C3—C2—H2120.2N15—C40—C39123.6 (3)
N2—C3—C4123.1 (4)N15—C40—H40118.2
N2—C3—C2121.4 (4)C39—C40—H40118.2
C4—C3—C2115.5 (4)O1—C41—O2121.9 (3)
C5—C4—C3120.7 (4)O1—C41—O3122.1 (3)
C5—C4—H4119.6O2—C41—O3116.0 (3)
C3—C4—H4119.6O1—C41—Ni1172.2 (2)
N1—C5—C4124.3 (4)O2—C41—Ni159.39 (16)
N1—C5—H5117.8O3—C41—Ni157.03 (16)
C4—C5—H5117.8C1—N1—C5114.4 (3)
N3—C6—C7124.0 (3)C1—N1—Ni1122.6 (2)
N3—C6—H6118.0C5—N1—Ni1121.4 (2)
C7—C6—H6118.0C3—N2—H2A120.0
C6—C7—C8120.2 (4)C3—N2—H2B120.0
C6—C7—H7119.9H2A—N2—H2B120.0
C8—C7—H7119.9C10—N3—C6115.3 (3)
N4—C8—C7121.4 (4)C10—N3—Ni1127.2 (2)
N4—C8—C9122.3 (4)C6—N3—Ni1117.4 (2)
C7—C8—C9116.3 (3)C8—N4—H4A120.0
C10—C9—C8119.4 (3)C8—N4—H4B120.0
C10—C9—H9120.3H4A—N4—H4B120.0
C8—C9—H9120.3C11—N5—C15115.3 (3)
N3—C10—C9124.7 (3)C11—N5—Ni1121.6 (2)
N3—C10—H10117.6C15—N5—Ni1123.1 (2)
C9—C10—H10117.6C13—N6—H6A120.0
N5—C11—C12125.1 (3)C13—N6—H6B120.0
N5—C11—H11117.4H6A—N6—H6B120.0
C12—C11—H11117.4C20—N7—C16115.6 (3)
C11—C12—C13119.6 (3)C20—N7—Ni1121.5 (2)
C11—C12—H12120.2C16—N7—Ni1121.4 (2)
C13—C12—H12120.2C18—N8—H8A120.0
N6—C13—C14122.5 (4)C18—N8—H8B120.0
N6—C13—C12121.7 (4)H8A—N8—H8B120.0
C14—C13—C12115.9 (3)C25—N9—C21116.0 (3)
C15—C14—C13120.1 (3)C25—N9—Ni2124.1 (2)
C15—C14—H14119.9C21—N9—Ni2118.8 (2)
C13—C14—H14119.9C23—N10—H10A120.0
N5—C15—C14124.0 (3)C23—N10—H10B120.0
N5—C15—H15118.0H10A—N10—H10B120.0
C14—C15—H15118.0C30—N11—C26115.3 (3)
N7—C16—C17124.2 (3)C30—N11—Ni2124.7 (3)
N7—C16—H16117.9C26—N11—Ni2120.0 (2)
C17—C16—H16117.9C28—N12—H12A120.0
C16—C17—C18119.7 (3)C28—N12—H12B120.0
C16—C17—H17120.1H12A—N12—H12B120.0
C18—C17—H17120.1C31—N13—C35115.3 (3)
N8—C18—C17121.7 (3)C31—N13—Ni2123.8 (2)
N8—C18—C19122.1 (3)C35—N13—Ni2120.7 (2)
C17—C18—C19116.2 (3)C33—N14—H14A120.0
C20—C19—C18119.4 (3)C33—N14—H14B120.0
C20—C19—H19120.3H14A—N14—H14B120.0
C18—C19—H19120.3C36—N15—C40116.2 (3)
N7—C20—C19124.7 (3)C36—N15—Ni2123.0 (2)
N7—C20—H20117.6C40—N15—Ni2120.4 (2)
C19—C20—H20117.6C38—N16—H16A120.0
N9—C21—C22123.8 (3)C38—N16—H16B120.0
N9—C21—H21118.1H16A—N16—H16B120.0
C22—C21—H21118.1N5—Ni1—N397.26 (11)
C21—C22—C23119.7 (3)N5—Ni1—O3100.55 (10)
C21—C22—H22120.2N3—Ni1—O3161.83 (11)
C23—C22—H22120.2N5—Ni1—N189.17 (11)
N10—C23—C22122.0 (3)N3—Ni1—N193.18 (11)
N10—C23—C24121.4 (3)O3—Ni1—N190.67 (10)
C22—C23—C24116.5 (3)N5—Ni1—N792.86 (11)
C25—C24—C23119.3 (3)N3—Ni1—N790.83 (11)
C25—C24—H24120.3O3—Ni1—N784.74 (10)
C23—C24—H24120.3N1—Ni1—N7175.25 (11)
N9—C25—C24124.5 (3)N5—Ni1—O2162.72 (10)
N9—C25—H25117.8N3—Ni1—O299.87 (10)
C24—C25—H25117.8O3—Ni1—O262.22 (9)
N11—C26—C27124.2 (4)N1—Ni1—O292.15 (10)
N11—C26—H26117.9N7—Ni1—O284.65 (10)
C27—C26—H26117.9N5—Ni1—C41131.62 (11)
C26—C27—C28120.3 (4)N3—Ni1—C41130.59 (11)
C26—C27—H27119.9O3—Ni1—C4131.29 (10)
C28—C27—H27119.9N1—Ni1—C4194.09 (11)
N12—C28—C29121.8 (4)N7—Ni1—C4181.35 (11)
N12—C28—C27122.5 (4)O2—Ni1—C4131.10 (10)
C29—C28—C27115.7 (3)N15—Ni2—O188.93 (10)
C30—C29—C28120.1 (4)N15—Ni2—N9174.15 (11)
C30—C29—H29120.0O1—Ni2—N985.33 (10)
C28—C29—H29120.0N15—Ni2—N1392.59 (11)
N11—C30—C29124.5 (4)O1—Ni2—N13172.51 (10)
N11—C30—H30117.7N9—Ni2—N1392.98 (11)
C29—C30—H30117.7N15—Ni2—N1190.78 (11)
N13—C31—C32125.1 (3)O1—Ni2—N1190.36 (10)
N13—C31—H31117.4N9—Ni2—N1190.32 (11)
C32—C31—H31117.4N13—Ni2—N1196.96 (11)
C31—C32—C33119.3 (3)N15—Ni2—O1W87.83 (10)
C31—C32—H32120.4O1—Ni2—O1W88.61 (9)
C33—C32—H32120.4N9—Ni2—O1W90.96 (10)
N14—C33—C34122.3 (3)N13—Ni2—O1W84.12 (10)
N14—C33—C32121.6 (4)N11—Ni2—O1W178.28 (11)
C34—C33—C32116.1 (3)C41—O1—Ni2129.0 (2)
C35—C34—C33120.0 (3)Ni2—O1W—H1W187.2
C35—C34—H34120.0Ni2—O1W—H2W1108.0
C33—C34—H34120.0H1W1—O1W—H2W1107.7
N13—C35—C34124.1 (3)C41—O2—Ni189.51 (19)
N13—C35—H35117.9C41—O3—Ni191.67 (19)
C34—C35—H35117.9H1W2—O2W—H2W2107.8
N15—C36—C37124.6 (3)H1W3—O3W—H2W3107.4
N15—C36—H36117.7H1W4—O4W—H2W4107.8
C37—C36—H36117.7H1W5—O5WA—H2W5107.7
C36—C37—C38119.1 (3)H1WA—O5WB—H2WB108.2
C36—C37—H37120.4H1W6—O6WA—H2W6107.7
C38—C37—H37120.4H1WC—O6WB—H2WD107.7
N16—C38—C39121.6 (3)
N1—C1—C2—C3−0.3 (6)C6—N3—Ni1—N5−177.3 (3)
C1—C2—C3—N2−177.5 (4)C10—N3—Ni1—O3−162.3 (3)
C1—C2—C3—C41.9 (6)C6—N3—Ni1—O314.2 (5)
N2—C3—C4—C5177.0 (5)C10—N3—Ni1—N195.8 (3)
C2—C3—C4—C5−2.4 (7)C6—N3—Ni1—N1−87.8 (3)
C3—C4—C5—N11.3 (8)C10—N3—Ni1—N7−86.8 (3)
N3—C6—C7—C8−0.2 (6)C6—N3—Ni1—N789.7 (3)
C6—C7—C8—N4177.3 (4)C10—N3—Ni1—O2−171.5 (3)
C6—C7—C8—C9−0.4 (6)C6—N3—Ni1—O25.0 (3)
N4—C8—C9—C10−177.2 (4)C10—N3—Ni1—C41−166.1 (3)
C7—C8—C9—C100.4 (5)C6—N3—Ni1—C4110.4 (3)
C8—C9—C10—N30.1 (6)C1—N1—Ni1—N5−99.9 (3)
N5—C11—C12—C13−1.1 (6)C5—N1—Ni1—N565.0 (3)
C11—C12—C13—N6−179.4 (4)C1—N1—Ni1—N3162.9 (3)
C11—C12—C13—C141.2 (5)C5—N1—Ni1—N3−32.2 (3)
N6—C13—C14—C15−179.6 (4)C1—N1—Ni1—O30.6 (3)
C12—C13—C14—C15−0.2 (6)C5—N1—Ni1—O3165.5 (3)
C13—C14—C15—N5−1.1 (6)C1—N1—Ni1—O262.9 (3)
N7—C16—C17—C18−2.8 (6)C5—N1—Ni1—O2−132.3 (3)
C16—C17—C18—N8−175.2 (3)C1—N1—Ni1—C4131.8 (3)
C16—C17—C18—C194.0 (5)C5—N1—Ni1—C41−163.3 (3)
N8—C18—C19—C20176.6 (3)C20—N7—Ni1—N5−152.6 (3)
C17—C18—C19—C20−2.6 (5)C16—N7—Ni1—N542.1 (3)
C18—C19—C20—N7−0.2 (6)C20—N7—Ni1—N3−55.3 (3)
N9—C21—C22—C231.6 (6)C16—N7—Ni1—N3139.4 (3)
C21—C22—C23—N10174.7 (3)C20—N7—Ni1—O3107.1 (3)
C21—C22—C23—C24−4.5 (5)C16—N7—Ni1—O3−58.3 (3)
N10—C23—C24—C25−175.0 (3)C20—N7—Ni1—O244.6 (3)
C22—C23—C24—C254.2 (5)C16—N7—Ni1—O2−120.8 (3)
C23—C24—C25—N9−0.9 (6)C20—N7—Ni1—C4175.7 (3)
N11—C26—C27—C28−0.6 (6)C16—N7—Ni1—C41−89.6 (3)
C26—C27—C28—N12178.8 (4)O2—C41—Ni1—N5179.89 (18)
C26—C27—C28—C290.5 (6)O3—C41—Ni1—N58.0 (3)
N12—C28—C29—C30−179.3 (4)O2—C41—Ni1—N3−10.4 (2)
C27—C28—C29—C30−0.9 (6)O3—C41—Ni1—N3177.73 (18)
C28—C29—C30—N111.5 (6)O2—C41—Ni1—O3171.9 (3)
N13—C31—C32—C330.4 (6)O2—C41—Ni1—N187.37 (19)
C31—C32—C33—N14−178.9 (4)O3—C41—Ni1—N1−84.53 (19)
C31—C32—C33—C341.3 (6)O2—C41—Ni1—N7−93.98 (19)
N14—C33—C34—C35179.1 (4)O3—C41—Ni1—N794.1 (2)
C32—C33—C34—C35−1.0 (6)O3—C41—Ni1—O2−171.9 (3)
C33—C34—C35—N13−1.0 (6)C36—N15—Ni2—O1−147.6 (3)
N15—C36—C37—C380.4 (6)C40—N15—Ni2—O140.4 (3)
C36—C37—C38—N16176.1 (4)C36—N15—Ni2—N1339.8 (3)
C36—C37—C38—C39−4.2 (5)C40—N15—Ni2—N13−132.2 (3)
N16—C38—C39—C40−175.0 (3)C36—N15—Ni2—N11−57.2 (3)
C37—C38—C39—C405.3 (5)C40—N15—Ni2—N11130.8 (3)
C38—C39—C40—N15−2.7 (6)C36—N15—Ni2—O1W123.8 (3)
C2—C1—N1—C5−0.9 (5)C40—N15—Ni2—O1W−48.2 (3)
C2—C1—N1—Ni1165.0 (3)C25—N9—Ni2—O1−127.7 (3)
C4—C5—N1—C10.4 (6)C21—N9—Ni2—O140.0 (3)
C4—C5—N1—Ni1−165.7 (4)C25—N9—Ni2—N1345.0 (3)
C9—C10—N3—C6−0.7 (5)C21—N9—Ni2—N13−147.3 (3)
C9—C10—N3—Ni1175.8 (3)C25—N9—Ni2—N11142.0 (3)
C7—C6—N3—C100.7 (6)C21—N9—Ni2—N11−50.4 (3)
C7—C6—N3—Ni1−176.2 (3)C25—N9—Ni2—O1W−39.1 (3)
C12—C11—N5—C15−0.2 (5)C21—N9—Ni2—O1W128.5 (3)
C12—C11—N5—Ni1−179.2 (3)C31—N13—Ni2—N15−151.3 (3)
C14—C15—N5—C111.3 (5)C35—N13—Ni2—N1533.6 (3)
C14—C15—N5—Ni1−179.7 (3)C31—N13—Ni2—N930.5 (3)
C19—C20—N7—C161.6 (5)C35—N13—Ni2—N9−144.6 (3)
C19—C20—N7—Ni1−164.6 (3)C31—N13—Ni2—N11−60.2 (3)
C17—C16—N7—C20−0.1 (5)C35—N13—Ni2—N11124.7 (3)
C17—C16—N7—Ni1166.1 (3)C31—N13—Ni2—O1W121.1 (3)
C24—C25—N9—C21−2.0 (5)C35—N13—Ni2—O1W−54.0 (3)
C24—C25—N9—Ni2165.9 (3)C30—N11—Ni2—N15104.0 (3)
C22—C21—N9—C251.7 (5)C26—N11—Ni2—N15−79.3 (3)
C22—C21—N9—Ni2−166.9 (3)C30—N11—Ni2—O1−167.0 (3)
C29—C30—N11—C26−1.5 (6)C26—N11—Ni2—O19.7 (3)
C29—C30—N11—Ni2175.4 (3)C30—N11—Ni2—N9−81.7 (3)
C27—C26—N11—C301.0 (6)C26—N11—Ni2—N995.0 (3)
C27—C26—N11—Ni2−176.0 (3)C30—N11—Ni2—N1311.3 (3)
C32—C31—N13—C35−2.3 (6)C26—N11—Ni2—N13−172.0 (3)
C32—C31—N13—Ni2−177.7 (3)O2—C41—O1—Ni2−157.8 (2)
C34—C35—N13—C312.6 (5)O3—C41—O1—Ni223.7 (5)
C34—C35—N13—Ni2178.1 (3)N15—Ni2—O1—C41−106.2 (3)
C37—C36—N15—C402.5 (5)N9—Ni2—O1—C4172.7 (3)
C37—C36—N15—Ni2−169.8 (3)N11—Ni2—O1—C41163.0 (3)
C39—C40—N15—C36−1.3 (5)O1W—Ni2—O1—C41−18.3 (3)
C39—C40—N15—Ni2171.2 (3)O1—C41—O2—Ni1−171.0 (3)
C11—N5—Ni1—N3−58.4 (3)O3—C41—O2—Ni17.6 (3)
C15—N5—Ni1—N3122.7 (3)N5—Ni1—O2—C41−0.3 (4)
C11—N5—Ni1—O3118.0 (3)N3—Ni1—O2—C41172.03 (19)
C15—N5—Ni1—O3−61.0 (3)O3—Ni1—O2—C41−4.74 (18)
C11—N5—Ni1—N1−151.5 (3)N1—Ni1—O2—C41−94.4 (2)
C15—N5—Ni1—N129.6 (3)N7—Ni1—O2—C4182.1 (2)
C11—N5—Ni1—N732.8 (3)O1—C41—O3—Ni1170.8 (3)
C15—N5—Ni1—N7−146.1 (3)O2—C41—O3—Ni1−7.8 (3)
C11—N5—Ni1—O2114.0 (4)N5—Ni1—O3—C41−173.93 (19)
C15—N5—Ni1—O2−65.0 (5)N3—Ni1—O3—C41−5.5 (4)
C11—N5—Ni1—C41113.8 (3)N1—Ni1—O3—C4196.8 (2)
C15—N5—Ni1—C41−65.2 (3)N7—Ni1—O3—C41−82.0 (2)
C10—N3—Ni1—N56.2 (3)O2—Ni1—O3—C414.72 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···O2Wi0.852.042.807 (4)150
N2—H2B···Cl1ii0.862.443.283 (4)166
O2W—H2W2···O1Wi0.852.352.807 (4)114
N4—H4A···Cl2iii0.862.613.405 (4)153
N6—H6A···Cl1i0.862.453.303 (4)170
N8—H8B···O1iv0.862.413.218 (4)157
N8—H8B···O2iv0.862.363.118 (4)147
O5WA—H2W5···Cl2i0.852.503.314 (6)161
N10—H10A···O2v0.862.102.880 (4)151
N10—H10B···Cl1ii0.862.483.308 (3)162
O5WB—H1WA···O1Wi0.852.142.843 (7)140
O5WB—H2WB···N14vi0.852.393.175 (8)154
N12—H12B···Cl2iv0.862.733.401 (4)137
N14—H14A···Cl1vii0.862.473.318 (4)168
N16—H16B···Cl2viii0.862.543.364 (4)162
C6—H6···N10v0.932.493.352 (5)155
C26—H26···N8iv0.932.573.413 (5)151
O1W—H1W1···O30.851.682.525 (3)171
O2W—H1W2···Cl20.852.533.155 (4)132
O2W—H2W2···O3W0.852.402.820 (8)111
N6—H6B···O2W0.862.222.971 (5)145
O4W—H1W4···Cl20.851.762.591 (8)166
N8—H8A···Cl10.862.503.350 (3)169
O5WA—H1W5···O1W0.852.242.802 (6)124
O6WA—H2W6···O4W0.852.032.870 (7)170
N16—H16A···Cl10.862.453.301 (4)170
C1—H1···O30.932.433.020 (4)121
C6—H6···O20.932.583.224 (4)127
C15—H15···N10.932.573.065 (4)114
C26—H26···O10.932.362.982 (4)124
C15—H15···Cg10.932.863.559 (5)133
C22—H22···Cg1v0.932.953.764 (5)147
N4—H4B···Cg2iii0.862.843.668 (5)163
C1—H1···Cg30.932.993.653 (5)130
N12—H12B···Cg3ix0.862.923.783 (5)177
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+1, −z; (v) −x+1, −y+2, −z; (vi) x+1, y−1, z; (vii) −x, −y+1, −z+1; (viii) x−1, y, z; (ix) −x, −y+2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W1···O2Wi0.852.042.807 (4)150
N2—H2B···Cl1ii0.862.443.283 (4)166
O2W—H2W2···O1Wi0.852.352.807 (4)114
N4—H4A···Cl2iii0.862.613.405 (4)153
N6—H6A···Cl1i0.862.453.303 (4)170
N8—H8B···O1iv0.862.413.218 (4)157
N8—H8B···O2iv0.862.363.118 (4)147
O5WA—H2W5···Cl2i0.852.503.314 (6)161
N10—H10A···O2v0.862.102.880 (4)151
N10—H10B···Cl1ii0.862.483.308 (3)162
O5WB—H1WA···O1Wi0.852.142.843 (7)140
O5WB—H2WB···N14vi0.852.393.175 (8)154
N12—H12B···Cl2iv0.862.733.401 (4)137
N14—H14A···Cl1vii0.862.473.318 (4)168
N16—H16B···Cl2viii0.862.543.364 (4)162
C6—H6···N10v0.932.493.352 (5)155
C26—H26···N8iv0.932.573.413 (5)151
O1W—H1W1···O30.851.682.525 (3)171
O2W—H1W2···Cl20.852.533.155 (4)132
O2W—H2W2···O3W0.852.402.820 (8)111
N6—H6B···O2W0.862.222.971 (5)145
O4W—H1W4···Cl20.851.762.591 (8)166
N8—H8A···Cl10.862.503.350 (3)169
O5WA—H1W5···O1W0.852.242.802 (6)124
O6WA—H2W6···O4W0.852.032.870 (7)170
N16—H16A···Cl10.862.453.301 (4)170
C1—H1···O30.932.433.020 (4)121
C6—H6···O20.932.583.224 (4)127
C15—H15···N10.932.573.065 (4)114
C26—H26···O10.932.362.982 (4)124
C15—H15···Cg10.932.863.559 (5)133
C22—H22···Cg1v0.932.953.764 (5)147
N4—H4B···Cg2iii0.862.843.668 (5)163
C1—H1···Cg30.932.993.653 (5)130
N12—H12B···Cg3ix0.862.923.783 (5)177
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+1, −z; (v) −x+1, −y+2, −z; (vi) x+1, y−1, z; (vii) −x, −y+1, −z+1; (viii) x−1, y, z; (ix) −x, −y+2, −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 the Universiti Sains Malaysia for a postdoctoral research fellowship.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Jebas, S. R., Balasubramanian, T. & Slawin, A. M. Z. (2007). Acta Cryst. E63, m1624–m1626.

Judge, S. & Bever, C. (2006). Pharmacol. Ther. 111, 224–259.

Schwid, S. B., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817–821.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Strupp, M., Kalla, R., Dichgans, M., Fraitinger, T., Glasauer, S. & Brandt, T. (2004). Neurology, 62, 1623–1625.