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Acta Cryst. (2007). E63, m2421    [ doi:10.1107/S160053680704130X ]

Bis(2-phenylethylammonium) tetraaquadichloridonickel(II) dichloride dihydrate

A. H. Arkenbout, A. Meetsma and T. T. M. Palstra

Abstract top

The crystal structure of the title compound, (C8H9NH3)2[NiCl2(H2O)4]Cl2·2H2O, was determined at 100 K. The nickel(II) ion is surrounded by an octahedron in which four water molecules and two Cl atoms are coordinated. These freestanding octahedra form a hydrogen-bonding network with the ammonium group of the 2-phenylethylammonium cations and the solvent water molecules and chloride ions. This results in sheets of freestanding octahedra alternating with layers of organic material.

Comment top

There is an interest to develop new multifunctional semiconductors that are easy to process and contain magnetic components. We present here the crystal structure of the title compound, which is a solution grown system build of organic conjugated molecules and paramagnetic Ni(II) ions. Every nickel(II) ion is surrounded by an octahedron in which 4 water molecules and 2 chlorine atoms are present. These octahedra are part of a complex network of hydrogen bonds between the ammonium groups, the water molecules and the free clorine ions, which stabilize this structure. The blue crystals of the title compound loose 20% of their weight when heated up to 350 K, leaving a pink amorphous powder, suggesting the evaporation of the crystal water. The material is paramagnetic down to 5 K. This lack of magnetic ordering can be explained by the large separation between the magnetic ions (d>6.631 Å) due to which the magnetic interactions are small and thus no magnetic ordering occurs.

Related literature top

The crystal structure of the organic part of the title compound was published by Arkenbout et al. (2007). Other examples of organic–inorganic hybrids are discussed by Papavassiliou (1997) and Mitzi (1999).

For related literature, see: Allen (2002); Bondi (1964).

Experimental top

The organic part was synthesized as described as in Arkenbout et al. (2007). The (2-phenylethyl)ammonium chloride was dissolved in water with NiCl2·6H2O in an approximate molar ratio of 2:1 with a slight excess of the Ni compound to account for the difference in solubility. After slow evaporation of the water blue crystals were obtained.

Refinement top

The hydrogen atoms of the C—H and N—H bonds were generated by geometrical considerations, constrained to idealized geometries, and allowed to ride on the carrier atoms with an isotropic displacement parameter related to the equivalent displacement parameter of their carrier atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C and ammonium). The methyl-groups and ammonium were refined as rigid groups, which were allowed to rotate freely. Assigned values of bond distances: secondary C—H2 = 0.99 Å, methyl C—H3 = 0.98 Å and aromatic C—H = 0.95 Å, N—H = 0.91 Å. The hydrogen atoms of the O—H bonds were restrained to a target value of 0.84 (2) Å and their isotropic displacement parameters were set to 1.5 times the Ueq value of their parent atom.

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Perspective view of all the moieties of the asymmetric unit illustrating the configuration and the adopted numbering scheme. Displacement ellipsoids for non H-atoms are represented at 50% probability level. The H-atoms are drawn with arbitrary radii.
[Figure 2] Fig. 2. Polyhedral drawing of the crystal structure viewed down the a axis.
[Figure 3] Fig. 3. Polyhedral drawing of a portion of the crystal packing. The hydrogen bonds (red dashed lines) connect the different parts in the crystal structure.
Bis(2-phenylethylammonium) tetraaquadichloridonickel(II) dichloride dihydrate top
Crystal data top
(C8H12N1)2[NiCl2(H2O)4]Cl2·2H2OF000 = 1160
Mr = 552.98The final unit cell was obtained from the xyz centroids of 3790 reflections after integration using the SAINTPLUS software package (Bruker, 2000).
Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the finalatomic coordinates of the structure did not yield extra symmetry elements [Spek, A. L. (1988). J. Appl. Cryst. 21, 578–579; Le Page, Y. (1987). J. Appl. Cryst. 20, 264–269; Le Page, Y. (1988). J. Appl. Cryst. 21, 983–984]
Monoclinic, P21/cDx = 1.498 Mg m−3
Hall symbol: -P 2ybcMo Kα radiation
λ = 0.71073 Å
a = 7.6977 (10) ÅCell parameters from 3790 reflections
b = 29.540 (4) Åθ = 2.8–28.3º
c = 10.7808 (15) ŵ = 1.26 mm−1
β = 90.760 (2)ºT = 100 (1) K
V = 2451.2 (6) Å3Platelet, green
Z = 40.36 × 0.15 × 0.04 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4617 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2752 reflections with I > 2σ(I)
Monochromator: parallel mounted graphiteRint = 0.071
Detector resolution: 66.06 pixels mm-1θmax = 25.7º
T = 100(1) Kθmin = 2.7º
φ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		k = −36→36
Tmin = 0.625, Tmax = 0.951l = −13→12
17481 measured reflections
Refinement top
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.100  w = 1/[σ2(Fo2)]
S = 0.96(Δ/σ)max < 0.001
4617 reflectionsΔρmax = 0.49 e Å−3
300 parametersΔρmin = −0.37 e Å−3
12 restraintsExtinction correction: none
Primary atom site location: heavy-atom method
Crystal data top
(C8H12N1)2[NiCl2(H2O)4]Cl2·2H2OV = 2451.2 (6) Å3
Mr = 552.98Z = 4
Monoclinic, P21/cMo Kα
a = 7.6977 (10) ŵ = 1.26 mm−1
b = 29.540 (4) ÅT = 100 (1) K
c = 10.7808 (15) Å0.36 × 0.15 × 0.04 mm
β = 90.760 (2)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4617 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)		2752 reflections with I > 2σ(I)
Tmin = 0.625, Tmax = 0.951Rint = 0.071
17481 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04212 restraints
wR(F2) = 0.100H atoms treated by a mixture of
independent and constrained refinement
S = 0.96Δρmax = 0.49 e Å−3
4617 reflectionsΔρmin = −0.37 e Å−3
300 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.75797 (5)0.00017 (2)0.25209 (4)0.0106 (1)
Cl110.73394 (10)0.08087 (3)0.25394 (8)0.0145 (3)
Cl120.78520 (10)−0.08070 (3)0.25237 (8)0.0137 (3)
O110.7986 (3)0.00252 (9)0.0639 (3)0.0234 (10)
O121.0194 (3)0.00810 (8)0.2918 (3)0.0164 (9)
O130.4969 (3)−0.00747 (8)0.2107 (3)0.0176 (9)
O140.7171 (3)−0.00256 (9)0.4403 (2)0.0200 (9)
H110.788 (5)−0.0197 (10)0.016 (3)0.0352*
H11'0.828 (5)0.0248 (9)0.022 (3)0.0352*
H121.069 (4)−0.0170 (7)0.298 (4)0.0247*
H12'1.075 (4)0.0239 (11)0.242 (3)0.0247*
H130.441 (4)0.0152 (8)0.186 (4)0.0263*
H13'0.446 (4)−0.0198 (12)0.269 (3)0.0263*
H140.678 (5)−0.0252 (9)0.477 (3)0.0301*
H14'0.711 (5)0.0200 (9)0.487 (3)0.0301*
N20.0460 (3)0.09932 (10)0.4585 (3)0.0143 (10)
C210.0035 (4)0.14876 (12)0.4579 (3)0.0154 (11)
C220.0760 (4)0.17128 (12)0.3429 (3)0.0169 (11)
C230.0250 (4)0.22067 (12)0.3331 (3)0.0129 (11)
C240.0765 (4)0.25214 (12)0.4228 (3)0.0149 (11)
C250.0319 (4)0.29747 (12)0.4107 (4)0.0175 (11)
C26−0.0663 (4)0.31217 (12)0.3092 (3)0.0169 (11)
C27−0.1209 (4)0.28086 (12)0.2206 (3)0.0148 (11)
C28−0.0751 (4)0.23574 (12)0.2326 (3)0.0144 (11)
H20−0.014720.085230.396620.0214*
H20'0.016690.087120.532820.0214*
H20"0.161850.095560.446310.0214*
H210.053580.163230.533070.0183*
H21'−0.124170.152810.459330.0183*
H220.204290.168910.345040.0202*
H22'0.033050.155000.268340.0202*
H240.142880.242450.492830.0180*
H250.068520.318590.472170.0211*
H26−0.095710.343250.300420.0202*
H27−0.189830.290460.151780.0175*
H28−0.112460.214680.171180.0171*
N30.5437 (3)0.09956 (10)−0.0599 (3)0.0155 (10)
C310.5003 (4)0.14887 (12)−0.0633 (3)0.0150 (11)
C320.5800 (4)0.17265 (12)0.0481 (3)0.0184 (11)
C330.5255 (4)0.22157 (12)0.0587 (3)0.0145 (11)
C340.4268 (4)0.23574 (12)0.1585 (3)0.0149 (11)
C350.3802 (4)0.28090 (12)0.1721 (3)0.0155 (11)
C360.4301 (4)0.31266 (13)0.0857 (3)0.0181 (11)
C370.5282 (4)0.29877 (12)−0.0163 (3)0.0158 (11)
C380.5753 (4)0.25395 (12)−0.0296 (3)0.0132 (11)
H300.660400.09592−0.068160.0231*
H30'0.487280.08513−0.123160.0231*
H30"0.509990.087610.013770.0231*
H310.372590.15280−0.063130.0183*
H31'0.545150.16247−0.140480.0183*
H320.546010.156400.124290.0223*
H32'0.708160.171190.042400.0223*
H340.390580.214220.218380.0176*
H350.313610.289980.241330.0184*
H360.398300.343530.095100.0219*
H370.562520.32035−0.076600.0188*
H380.641770.24491−0.098950.0158*
Cl40.72994 (10)0.07568 (3)0.64530 (8)0.0146 (3)
Cl50.24825 (10)0.07499 (3)0.13985 (8)0.0151 (3)
O60.4138 (3)0.08084 (9)0.4482 (2)0.0155 (8)
H60.489 (3)0.0848 (13)0.505 (2)0.0233*
H6'0.468 (4)0.0815 (12)0.3807 (19)0.0233*
O70.9133 (3)0.08230 (9)0.9544 (3)0.0180 (9)
H70.977 (4)0.0833 (13)0.892 (2)0.0271*
H7'0.986 (4)0.0897 (13)1.009 (3)0.0271*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0120 (14)0.0184 (19)0.0124 (19)−0.0021 (12)0.0006 (12)0.0001 (14)
C210.0134 (16)0.014 (2)0.019 (2)0.0008 (14)0.0032 (16)−0.0017 (17)
C220.0158 (17)0.019 (2)0.016 (2)−0.0001 (15)0.0022 (16)−0.0003 (17)
C230.0117 (16)0.016 (2)0.011 (2)−0.0003 (14)0.0047 (15)−0.0018 (17)
C240.0138 (17)0.020 (2)0.011 (2)0.0001 (15)0.0003 (15)0.0007 (18)
C250.0146 (17)0.019 (2)0.019 (2)−0.0056 (15)0.0019 (16)−0.0027 (18)
C260.0169 (18)0.018 (2)0.016 (2)0.0015 (15)0.0031 (16)0.0034 (18)
C270.0133 (17)0.023 (2)0.008 (2)0.0002 (15)−0.0003 (15)0.0033 (17)
C280.0122 (16)0.019 (2)0.012 (2)−0.0019 (15)0.0043 (16)−0.0037 (17)
N30.0160 (15)0.0155 (18)0.015 (2)−0.0020 (12)0.0018 (13)−0.0008 (13)
C310.0148 (16)0.015 (2)0.015 (2)0.0044 (15)−0.0024 (15)−0.0025 (17)
C320.0190 (18)0.017 (2)0.019 (2)0.0013 (15)−0.0014 (16)−0.0002 (17)
C330.0114 (16)0.020 (2)0.012 (2)−0.0020 (14)−0.0047 (15)−0.0036 (17)
C340.0125 (17)0.019 (2)0.013 (2)−0.0011 (14)−0.0034 (15)0.0018 (17)
C350.0106 (16)0.021 (2)0.015 (2)−0.0018 (14)0.0008 (15)−0.0034 (18)
C360.0151 (17)0.018 (2)0.021 (2)0.0028 (15)−0.0044 (16)−0.0026 (18)
C370.0114 (17)0.021 (2)0.015 (2)−0.0038 (14)−0.0049 (15)0.0037 (18)
C380.0117 (16)0.020 (2)0.008 (2)0.0020 (14)−0.0008 (15)−0.0024 (17)
Ni10.0095 (2)0.0126 (2)0.0098 (3)−0.0001 (2)0.0005 (2)0.0010 (2)
Cl110.0146 (4)0.0134 (5)0.0155 (6)0.0001 (3)−0.0002 (4)0.0009 (4)
Cl120.0142 (4)0.0132 (5)0.0136 (5)−0.0006 (3)−0.0001 (4)0.0009 (4)
O110.0407 (15)0.0185 (17)0.0113 (18)−0.0108 (14)0.0076 (13)−0.0010 (14)
O120.0131 (12)0.0171 (16)0.0191 (18)−0.0021 (10)−0.0003 (11)0.0022 (13)
O130.0137 (12)0.0177 (16)0.0214 (18)0.0014 (11)0.0005 (11)0.0081 (13)
O140.0345 (14)0.0130 (16)0.0128 (18)−0.0047 (13)0.0066 (12)0.0001 (14)
O60.0166 (13)0.0197 (15)0.0102 (16)0.0001 (11)−0.0008 (11)−0.0002 (13)
O70.0130 (12)0.0231 (16)0.0181 (18)−0.0001 (11)0.0032 (11)0.0012 (14)
Cl40.0131 (4)0.0162 (5)0.0144 (5)−0.0013 (3)0.0011 (4)0.0001 (4)
Cl50.0143 (4)0.0160 (5)0.0150 (6)−0.0005 (3)0.0008 (4)0.0004 (4)
Geometric parameters (Å, °) top
Ni1—O132.065 (2)C24—C251.388 (5)
Ni1—O142.059 (2)C25—C261.391 (5)
Ni1—Cl122.3981 (11)C26—C271.391 (5)
Ni1—O112.058 (3)C27—C281.384 (5)
Ni1—Cl112.3912 (11)C21—H210.9900
Ni1—O122.065 (2)C21—H21'0.9900
O11—H110.84 (3)C22—H22'0.9900
O11—H11'0.83 (3)C22—H220.9900
O12—H120.84 (2)C24—H240.9500
O12—H12'0.83 (3)C25—H250.9500
O13—H130.84 (3)C26—H260.9500
O13—H13'0.83 (3)C27—H270.9500
O14—H14'0.84 (3)C28—H280.9500
O14—H140.84 (3)C31—C321.514 (5)
O6—H60.85 (2)C32—C331.510 (5)
O6—H6'0.84 (2)C33—C381.406 (5)
O7—H7'0.84 (3)C33—C341.390 (5)
O7—H70.84 (3)C34—C351.390 (5)
N2—C211.497 (5)C35—C361.380 (5)
N2—H20"0.9100C36—C371.404 (5)
N2—H200.9100C37—C381.381 (5)
N2—H20'0.9100C31—H310.9900
N3—C311.495 (5)C31—H31'0.9900
N3—H300.9100C32—H320.9900
N3—H30'0.9100C32—H32'0.9900
N3—H30"0.9100C34—H340.9500
C21—C221.520 (5)C35—H350.9500
C22—C231.514 (5)C36—H360.9500
C23—C281.394 (5)C37—H370.9500
C23—C241.395 (5)C38—H380.9500
Ni1···H30'i3.4300C31···H383.0600
Ni1···H7ii3.57 (3)C32···H28iii2.9700
Ni1···H20iii3.4300C33···H28iii3.0300
Ni1···H6'3.57 (3)C34···H24ix2.8800
Cl4···N2iii3.255 (3)C35···H24ix2.7300
Cl4···O143.198 (3)C35···H31'viii2.9000
Cl4···O13iv3.097 (3)C36···H21ix3.0300
Cl4···O63.213 (2)C36···H27iii3.0700
Cl4···C21iii3.645 (3)C36···H24ix2.9100
Cl5···N33.235 (3)C37···H27iii2.8200
Cl5···O133.185 (3)C37···H21'xi3.0500
Cl5···O11i3.190 (3)C37···H22ix3.0400
Cl5···O12v3.125 (3)C37···H34ix3.0600
Cl11···C21iii3.611 (3)C38···H31'2.9600
Cl11···O143.183 (3)C38···H27iii2.8600
Cl11···O63.255 (2)H6···Cl42.39 (2)
Cl11···N2iii3.285 (3)H6···H36viii2.4400
Cl11···O133.215 (3)H6···H14iv2.19 (5)
Cl11···O113.135 (3)H6···H14'2.58 (5)
Cl11···O123.097 (3)H6'···H20"2.5000
Cl12···O133.127 (3)H6'···H14iv2.54 (4)
Cl12···O143.120 (3)H6'···Cl112.48 (3)
Cl12···C31i3.595 (3)H6'···Ni13.57 (3)
Cl12···N2iv3.406 (3)H6'···Cl53.09 (2)
Cl12···O123.208 (3)H11···Cl5i2.36 (3)
Cl12···N3i3.300 (3)H11'···H7vii2.51 (5)
Cl12···O113.192 (3)H11'···O7vii1.97 (3)
Cl12···O7ii3.240 (3)H11'···H7'vii2.28 (5)
Cl4···H20'iii2.5500H12···Cl4ii2.40 (3)
Cl4···H14'2.37 (3)H12'···Cl5iii2.30 (3)
Cl4···H62.39 (2)H12'···H20iii2.5600
Cl4···H13'iv2.33 (3)H13···Cl52.36 (3)
Cl5···H132.36 (3)H13'···Cl4iv2.33 (3)
Cl5···H12'v2.30 (3)H13'···H30'i2.5500
Cl5···H6'3.09 (2)H14···H6iv2.19 (5)
Cl5···H30"2.4700H14···O6iv1.97 (3)
Cl5···H11i2.36 (3)H14···H6'iv2.54 (4)
Cl11···H20iii2.4600H14···H20"iv2.5500
Cl11···H14'3.10 (3)H14'···Cl42.37 (3)
Cl11···H133.06 (3)H14'···H62.58 (5)
Cl11···H6'2.48 (3)H20···Cl11v2.4600
Cl11···H30"3.1000H20···Ni1v3.4300
Cl11···H323.0000H20···H22'2.5100
Cl11···H12'3.12 (3)H20···H12'v2.5600
Cl11···H11'3.09 (3)H20···O12v2.5600
Cl12···H122.92 (3)H20'···Cl4v2.5500
Cl12···H143.05 (3)H20'···Cl12iv2.7600
Cl12···H20'iv2.7600H20"···O61.9900
Cl12···H113.12 (3)H20"···H6'2.5000
Cl12···H7ii2.42 (3)H20"···H222.4500
Cl12···H36vi3.1300H20"···H14iv2.5500
Cl12···H30'i2.5100H21···H242.4800
O6···O14iv2.800 (4)H21···C27viii2.9500
O6···Cl43.213 (2)H21···C36viii3.0300
O6···Cl113.255 (2)H21···C242.8900
O6···N22.887 (3)H21'···C37x3.0500
O11···O132.843 (4)H21'···H37x2.5600
O11···O7vii2.785 (4)H22···H20"2.4500
O11···O122.974 (4)H22···H342.4000
O11···Cl123.192 (3)H22···C37viii3.0400
O11···Cl5i3.190 (3)H22'···H202.5100
O11···Cl113.135 (3)H22'···H282.3300
O12···N2iii3.244 (4)H24···C34viii2.8800
O12···O142.859 (3)H24···C35viii2.7300
O12···Cl4ii3.205 (3)H24···C36viii2.9100
O12···Cl5iii3.125 (3)H24···H212.4800
O12···O112.974 (4)H24···C212.9900
O12···Cl113.097 (3)H25···H31viii2.5200
O12···Cl123.208 (3)H26···H7xii2.4500
O13···N3i3.182 (4)H26···O7xii2.7600
O13···O142.985 (4)H27···C38v2.8600
O13···Cl53.185 (3)H27···C37v2.8200
O13···Cl123.127 (3)H27···C36v3.0700
O13···Cl4iv3.097 (3)H28···C32v2.9700
O13···Cl113.215 (3)H28···H32'v2.3300
O13···O112.843 (4)H28···H22'2.3300
O14···Cl43.198 (3)H28···C25ix3.0500
O14···O6iv2.800 (4)H28···C33v3.0300
O14···Cl123.120 (3)H30···O7vii2.0000
O14···O132.985 (4)H30···H7vii2.5100
O14···Cl113.183 (3)H30···H32'2.5500
O14···O122.859 (3)H30'···Ni1i3.4300
O6···H14iv1.97 (3)H30'···H13'i2.5500
O6···H20"1.9900H30'···Cl12i2.5100
O6···H36viii2.7400H30'···O13i2.4800
O11···H12'2.92 (3)H30'···Cl4vii3.1500
O12···H20iii2.5600H30"···H322.3700
O13···H30'i2.4800H30"···Cl113.1000
O14···H13'2.82 (3)H30"···Cl52.4700
N2···Cl12iv3.406 (3)H31···H25ix2.5200
N2···O62.887 (3)H31···C25ix3.0200
N2···O12v3.244 (4)H31'···C35ix2.9000
N2···Cl11v3.285 (3)H31'···C382.9600
N2···Cl4v3.255 (3)H31'···H382.5800
N3···Cl12i3.300 (3)H31'···H35ix2.5900
N3···O13i3.182 (4)H32···H30"2.3700
N3···Cl53.235 (3)H32···H342.3300
N3···O7vii2.893 (3)H32···Cl113.0000
C21···Cl11v3.611 (3)H32'···C25xi3.0300
C21···Cl4v3.645 (3)H32'···H28iii2.3300
C24···C28viii3.571 (5)H32'···H302.5500
C28···C24ix3.571 (5)H34···C37viii3.0600
C31···Cl12i3.595 (3)H34···H322.3300
C34···C38viii3.550 (5)H34···H222.4000
C38···C34ix3.550 (5)H34···C223.0600
C21···H242.9900H34···C233.0900
C22···H343.0600H35···C263.0900
C23···H343.0900H35···H31'viii2.5900
C24···H352.9200H35···C242.9200
C24···H212.8900H35···C252.8600
C25···H32'x3.0300H36···O6ix2.7400
C25···H31viii3.0200H36···Cl12xiii3.1300
C25···H28viii3.0500H36···H6ix2.4400
C25···H352.8600H37···H21'xi2.5600
C26···H38x2.9900H38···C28xi2.9100
C26···H353.0900H38···C27xi2.7900
C27···H21ix2.9500H38···C313.0600
C27···H38x2.7900H38···H31'2.5800
C28···H38x2.9100H38···C26xi2.9900
Cl12—Ni1—O1291.59 (7)H21—C21—H21'108.00
Cl12—Ni1—O1388.64 (7)C22—C21—H21'110.00
Cl12—Ni1—O1488.52 (8)N2—C21—H21110.00
O11—Ni1—O1292.30 (11)C22—C21—H21110.00
O11—Ni1—O1387.18 (11)N2—C21—H21'110.00
O11—Ni1—O14179.68 (11)C23—C22—H22109.00
O12—Ni1—O13179.44 (12)C21—C22—H22'109.00
O12—Ni1—O1487.79 (11)C23—C22—H22'109.00
O13—Ni1—O1492.73 (11)C21—C22—H22109.00
Cl11—Ni1—Cl12179.21 (3)H22—C22—H22'108.00
Cl11—Ni1—O1189.28 (8)C25—C24—H24120.00
Cl11—Ni1—O1287.73 (7)C23—C24—H24120.00
Cl11—Ni1—O1392.04 (7)C26—C25—H25120.00
Cl11—Ni1—O1491.03 (8)C24—C25—H25120.00
Cl12—Ni1—O1191.17 (8)C25—C26—H26120.00
Ni1—O11—H11'128 (2)C27—C26—H26120.00
H11—O11—H11'108 (3)C28—C27—H27120.00
Ni1—O11—H11125 (2)C26—C27—H27120.00
H12—O12—H12'108 (3)C27—C28—H28119.00
Ni1—O12—H12111 (2)C23—C28—H28119.00
Ni1—O12—H12'116 (2)N3—C31—C32110.2 (3)
H13—O13—H13'110 (3)C31—C32—C33113.2 (3)
Ni1—O13—H13'111 (2)C32—C33—C34120.2 (3)
Ni1—O13—H13118 (2)C34—C33—C38118.4 (3)
Ni1—O14—H14124 (2)C32—C33—C38121.4 (3)
Ni1—O14—H14'125 (2)C33—C34—C35121.0 (3)
H14—O14—H14'109 (3)C34—C35—C36120.5 (3)
H6—O6—H6'106 (2)C35—C36—C37119.2 (3)
H7—O7—H7'99 (3)C36—C37—C38120.4 (3)
C21—N2—H20'109.00C33—C38—C37120.5 (3)
C21—N2—H20"109.00C32—C31—H31110.00
H20—N2—H20"109.00C32—C31—H31'110.00
H20'—N2—H20"110.00N3—C31—H31110.00
C21—N2—H20109.00N3—C31—H31'110.00
H20—N2—H20'109.00H31—C31—H31'108.00
C31—N3—H30"109.00H32—C32—H32'108.00
H30—N3—H30'109.00C31—C32—H32'109.00
H30'—N3—H30"109.00C31—C32—H32109.00
C31—N3—H30109.00C33—C32—H32109.00
H30—N3—H30"109.00C33—C32—H32'109.00
C31—N3—H30'110.00C33—C34—H34120.00
N2—C21—C22110.4 (3)C35—C34—H34119.00
C21—C22—C23112.4 (3)C34—C35—H35120.00
C24—C23—C28118.4 (3)C36—C35—H35120.00
C22—C23—C28120.1 (3)C37—C36—H36120.00
C22—C23—C24121.5 (3)C35—C36—H36120.00
C23—C24—C25120.7 (3)C36—C37—H37120.00
C24—C25—C26120.4 (3)C38—C37—H37120.00
C25—C26—C27119.3 (3)C37—C38—H38120.00
C26—C27—C28120.1 (3)C33—C38—H38120.00
C23—C28—C27121.2 (3)
N2—C21—C22—C23175.8 (2)N3—C31—C32—C33−173.6 (2)
C21—C22—C23—C2462.1 (4)C31—C32—C33—C34115.0 (3)
C21—C22—C23—C28−118.2 (3)C31—C32—C33—C38−66.3 (4)
C22—C23—C24—C25178.5 (3)C32—C33—C34—C35177.9 (3)
C28—C23—C24—C25−1.3 (5)C38—C33—C34—C35−0.9 (5)
C22—C23—C28—C27−178.9 (3)C32—C33—C38—C37−178.2 (3)
C24—C23—C28—C270.8 (5)C34—C33—C38—C370.6 (5)
C23—C24—C25—C260.5 (5)C33—C34—C35—C360.6 (5)
C24—C25—C26—C270.7 (5)C34—C35—C36—C370.2 (5)
C25—C26—C27—C28−1.1 (5)C35—C36—C37—C38−0.5 (5)
C26—C27—C28—C230.4 (5)C36—C37—C38—C330.1 (5)
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z+1; (iii) x+1, y, z; (iv) −x+1, −y, −z+1; (v) x−1, y, z; (vi) −x+1, y−1/2, −z+1/2; (vii) x, y, z−1; (viii) x, −y+1/2, z+1/2; (ix) x, −y+1/2, z−1/2; (x) x−1, −y+1/2, z+1/2; (xi) x+1, −y+1/2, z−1/2; (xii) x−1, −y+1/2, z−1/2; (xiii) −x+1, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···Cl40.85 (2)2.39 (2)3.213 (2)164 (3)
O6—H6'···Cl110.84 (2)2.48 (3)3.255 (2)154 (2)
O11—H11···Cl5i0.84 (3)2.36 (3)3.190 (3)172 (3)
O11—H11'···O7vii0.83 (3)1.97 (3)2.785 (4)169 (3)
O12—H12···Cl4ii0.84 (2)2.40 (3)3.205 (3)163 (3)
O12—H12'···Cl5iii0.83 (3)2.30 (3)3.125 (3)168 (3)
O13—H13···Cl50.84 (3)2.36 (3)3.185 (3)171 (3)
O13—H13'···Cl4iv0.83 (3)2.33 (3)3.097 (3)153 (3)
O14—H14···O6iv0.84 (3)1.97 (3)2.800 (4)176 (3)
O14—H14'···Cl40.84 (3)2.37 (3)3.198 (3)169 (3)
N2—H20···Cl11v0.91002.46003.285 (3)151.00
N2—H20···O12v0.91002.56003.244 (4)133.00
N2—H20'···Cl4v0.91002.55003.255 (3)134.00
N2—H20'···Cl12iv0.91002.76003.406 (3)129.00
N2—H20"···O60.91001.99002.887 (3)170.00
N3—H30···O7vii0.91002.00002.893 (3)166.00
N3—H30'···Cl12i0.91002.51003.300 (3)146.00
N3—H30'···O13i0.91002.48003.182 (4)134.00
N3—H30"···Cl50.91002.47003.235 (3)141.00
Symmetry codes: (i) −x+1, −y, −z; (vii) x, y, z−1; (ii) −x+2, −y, −z+1; (iii) x+1, y, z; (iv) −x+1, −y, −z+1; (v) x−1, y, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···Cl40.85 (2)2.39 (2)3.213 (2)164 (3)
O6—H6'···Cl110.84 (2)2.48 (3)3.255 (2)154 (2)
O11—H11···Cl5i0.84 (3)2.36 (3)3.190 (3)172 (3)
O11—H11'···O7ii0.83 (3)1.97 (3)2.785 (4)169 (3)
O12—H12···Cl4iii0.84 (2)2.40 (3)3.205 (3)163 (3)
O12—H12'···Cl5iv0.83 (3)2.30 (3)3.125 (3)168 (3)
O13—H13···Cl50.84 (3)2.36 (3)3.185 (3)171 (3)
O13—H13'···Cl4v0.83 (3)2.33 (3)3.097 (3)153 (3)
O14—H14···O6v0.84 (3)1.97 (3)2.800 (4)176 (3)
O14—H14'···Cl40.84 (3)2.37 (3)3.198 (3)169 (3)
N2—H20···Cl11vi0.91002.46003.285 (3)151.00
N2—H20···O12vi0.91002.56003.244 (4)133.00
N2—H20'···Cl4vi0.91002.55003.255 (3)134.00
N2—H20'···Cl12v0.91002.76003.406 (3)129.00
N2—H20"···O60.91001.99002.887 (3)170.00
N3—H30···O7ii0.91002.00002.893 (3)166.00
N3—H30'···Cl12i0.91002.51003.300 (3)146.00
N3—H30'···O13i0.91002.48003.182 (4)134.00
N3—H30"···Cl50.91002.47003.235 (3)141.00
Symmetry codes: (i) −x+1, −y, −z; (ii) x, y, z−1; (iii) −x+2, −y, −z+1; (iv) x+1, y, z; (v) −x+1, −y, −z+1; (vi) x−1, y, z.
Acknowledgements top

We thank J. Baas for technical assistance, O. D. Jurchescu for discussions and the NanoNed for funding.

references
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