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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m144.
Published online 2010 January 13. doi:  10.1107/S1600536810000802
PMCID: PMC2979795

Tris(1,10-phenanthroline)nickel(II) dichromate tetra­hydrate

Abstract

The asymmetric unit of the title compound, [Ni(C12H8N2)3][Cr2O7]·4H2O, contains one cation, one anion and four water mol­ecules, three of which are disordered over two sites with equal occupancies. In the cation, the metal centre is coordinated by six N atoms from three 1,10-phenanthroline ligands in a distorted octa­hedral geometry. The [Cr2O7]2− anion exhibits a staggered conformation. The crystal packing is stabilized by inter­molecular O—H(...)O hydrogen bonds and π–π inter­actions, evidenced by short distances of 3.531 (5) Å between the centroids of aromatic rings.

Related literature

For related structures, see: Ejsmont et al. (2002 [triangle]); Suescun et al. (1999 [triangle]); Wang et al. (2007 [triangle]); Wiehl et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m144-scheme1.jpg

Experimental

Crystal data

  • [Ni(C12H8N2)3][Cr2O7]·4H2O
  • M r = 887.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m144-efi1.jpg
  • a = 26.899 (2) Å
  • b = 17.8121 (16) Å
  • c = 17.3656 (18) Å
  • β = 105.274 (2)°
  • V = 8026.5 (13) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.06 mm−1
  • T = 298 K
  • 0.14 × 0.12 × 0.11 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.866, T max = 0.892
  • 21223 measured reflections
  • 7229 independent reflections
  • 2790 reflections with I > 2σ(I)
  • R int = 0.129

Refinement

  • R[F 2 > 2σ(F 2)] = 0.077
  • wR(F 2) = 0.218
  • S = 1.06
  • 7229 reflections
  • 532 parameters
  • H-atom parameters constrained
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000802/cv2680sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000802/cv2680Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Metal complexes containing the chromate(VI) or dichromate(VI) anions, CrO42- or Cr2O72-, attract attention owing to their various properties (Ejsmont et al., 2002). 1,10-Phenanthroline (phen), which is the parent of an important class of chelating agents, has been widely used in the construction of supramolecular architectures. Some Nickel phenanthroline complexes have been synthesized and reported (Suescun et al., 1999; Wang et al., 2007; Wiehl et al., 2008). As a continuation of these studies, I now report the crystal structure of the title complex.

The title structure (Fig. 1) is build up of one Ni atom, three coordination phenanthroline ligand, dichromate and four free water molecules. Ni center is coordinated with six N atoms from three 1,10-phenanthroline ligands, presenting a distorted octahedral geometry. The Ni—N and Cr—O bond lengths are in the ranges 2.064 (7)–2.115 (7) and 1.583 (7)–1.786 (6) Å, respectively. The bond angles O—Cr—O, N—Ni—N are in the ranges of 107.1 (3)–111.4 (4) and 78.6 (3)–168.9 (3) °, respectively. The mean Cr—O bond lengths and O—Cr—O bond angles are similar to the reported earlier (Ejsmont et al., 2002).

The crystal packing is stabilized by intermolecular O—H···O hydrogen bonds (Table 1) and π-π interactions evidenced by short distance of 3.531 (5) Å between the centroids of aromatic rings.

Experimental

All commercially obtained reagent-grade chemicals were used without further purication. A mixture of NiCl2 (0.1 mmol, 0.014 g), 1,10-phenanthroline (0.1 mmol, 0.018 g), K2CrO4 (0.1 mmol, 0.019 g) and H3BO3 (0.1 mmol, 0.006 g) were added into 20 ml water with 20%(v/v) ethanol and heated for 12 h at 140 °. The solution was obtained by filtration after cooling the reaction to room temperature. Yellow block single crystals suitable for X-ray measurements were obtained after a few weeks.

Refinement

All H atoms were geometrically positioned (C—H 0.93 Å, O—H 0.85 Å) and refined using a riding model, with Uiso (H) =1.2–1.5 Ueq of the parent atom.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. The lattice water molecules and H atoms are omitted for clarity.

Crystal data

[Ni(C12H8N2)3][Cr2O7]·4H2OF(000) = 3632
Mr = 887.39Dx = 1.469 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 26.899 (2) ÅCell parameters from 1859 reflections
b = 17.8121 (16) Åθ = 2.5–25.1°
c = 17.3656 (18) ŵ = 1.06 mm1
β = 105.274 (2)°T = 298 K
V = 8026.5 (13) Å3Block, yellow
Z = 80.14 × 0.12 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer7229 independent reflections
Radiation source: fine-focus sealed tube2790 reflections with I > 2σ(I)
graphiteRint = 0.129
[var phi] and ω scansθmax = 25.2°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −32→31
Tmin = 0.866, Tmax = 0.892k = −17→21
21223 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0732P)2] where P = (Fo2 + 2Fc2)/3
7229 reflections(Δ/σ)max = 0.001
532 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = −0.37 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Cr10.82179 (6)0.55759 (10)0.64402 (9)0.0650 (5)
Cr20.72271 (6)0.63263 (9)0.68533 (9)0.0587 (5)
Ni10.63211 (4)0.33221 (7)0.65097 (6)0.0490 (4)
N10.6607 (3)0.3733 (5)0.5584 (4)0.0494 (18)
N20.6566 (3)0.2337 (4)0.6091 (4)0.0509 (19)
N30.6977 (3)0.3555 (4)0.7406 (4)0.054 (2)
N40.6129 (3)0.2824 (4)0.7479 (4)0.060 (2)
N50.5576 (3)0.3205 (5)0.5728 (4)0.058 (2)
N60.5977 (3)0.4336 (4)0.6700 (4)0.056 (2)
O10.8457 (3)0.5751 (4)0.5699 (4)0.090 (2)
O20.8657 (3)0.5494 (5)0.7250 (4)0.118 (3)
O30.7903 (3)0.4816 (4)0.6280 (5)0.110 (3)
O40.7807 (2)0.6314 (4)0.6536 (4)0.078 (2)
O50.7274 (2)0.5758 (4)0.7583 (4)0.079 (2)
O60.7148 (3)0.7165 (4)0.7117 (4)0.092 (2)
O70.6742 (2)0.6079 (4)0.6147 (4)0.084 (2)
O80.6132 (3)0.7723 (5)0.6890 (6)0.156 (4)
H8C0.64490.76230.69450.187*
H8D0.60850.81890.67910.187*
O90.5502 (5)0.7309 (8)0.7989 (9)0.099 (5)0.50
H9C0.56930.74270.76890.119*0.50
H9D0.51910.73050.77080.119*0.25
H9A0.55370.76270.83650.119*0.25
O100.9278 (6)0.5528 (10)0.5059 (12)0.149 (7)0.50
H10C0.90070.56080.52100.179*0.50
H10D0.92130.56190.45620.179*0.50
O110.9181 (7)0.5812 (11)0.3454 (13)0.161 (8)0.50
H11C0.89300.56220.31050.193*0.50
H11D0.94290.55000.35340.193*0.50
O120.5385 (6)0.1208 (10)0.3729 (11)0.142 (7)0.50
H12C0.53530.11940.42020.171*0.50
H12D0.54180.16630.36020.171*0.25
H12A0.51260.10070.34050.171*0.25
O130.5318 (8)0.0721 (11)0.6833 (14)0.187 (9)0.50
H13C0.56310.06540.70870.225*0.50
H13D0.53010.07580.63390.225*0.50
O140.5251 (8)0.0848 (12)0.5311 (14)0.189 (9)0.50
H14C0.49290.07620.52100.227*0.50
H14D0.53990.04540.52050.227*0.50
C10.6671 (3)0.4424 (6)0.5391 (6)0.059 (3)
H10.66090.48050.57200.071*
C20.6829 (3)0.4620 (6)0.4709 (6)0.067 (3)
H20.68700.51210.45870.080*
C30.6920 (3)0.4070 (7)0.4237 (6)0.063 (3)
H30.70240.41900.37820.076*
C40.6862 (3)0.3333 (6)0.4419 (5)0.055 (2)
C50.6716 (3)0.3183 (6)0.5123 (5)0.051 (2)
C60.6965 (3)0.2689 (7)0.3962 (6)0.066 (3)
H60.70620.27690.34920.079*
C70.6924 (4)0.2002 (7)0.4203 (6)0.067 (3)
H70.69850.16050.38920.080*
C80.6788 (3)0.1839 (6)0.4934 (6)0.057 (3)
C90.6681 (3)0.2430 (6)0.5386 (5)0.050 (2)
C100.6762 (3)0.1114 (6)0.5231 (6)0.069 (3)
H100.68210.07000.49410.083*
C110.6650 (4)0.1016 (6)0.5956 (6)0.070 (3)
H110.66340.05400.61660.085*
C120.6564 (3)0.1647 (7)0.6352 (6)0.064 (3)
H120.64980.15810.68480.077*
C130.7396 (4)0.3902 (5)0.7369 (6)0.062 (3)
H130.74330.40360.68690.074*
C140.7796 (4)0.4087 (6)0.8048 (6)0.073 (3)
H140.80930.43290.80010.088*
C150.7732 (4)0.3897 (6)0.8774 (6)0.073 (3)
H150.79860.40260.92320.088*
C160.7301 (4)0.3520 (6)0.8846 (6)0.065 (3)
C170.6925 (4)0.3355 (5)0.8137 (6)0.058 (2)
C180.6481 (4)0.2968 (5)0.8176 (6)0.056 (2)
C190.6411 (4)0.2738 (6)0.8903 (6)0.063 (3)
C200.6802 (5)0.2927 (6)0.9619 (6)0.076 (3)
H200.67630.27751.01120.092*
C210.7208 (5)0.3306 (6)0.9587 (6)0.081 (3)
H210.74450.34421.00610.097*
C220.5978 (5)0.2301 (6)0.8885 (6)0.075 (3)
H220.59270.21260.93630.090*
C230.5630 (4)0.2125 (6)0.8191 (6)0.075 (3)
H230.53450.18260.81800.090*
C240.5722 (4)0.2416 (6)0.7488 (6)0.071 (3)
H240.54820.23150.70050.085*
C250.5391 (4)0.2646 (6)0.5224 (6)0.066 (3)
H250.56030.22400.51960.079*
C260.4877 (4)0.2658 (7)0.4726 (6)0.074 (3)
H260.47580.22700.43670.089*
C270.4568 (4)0.3230 (7)0.4781 (6)0.070 (3)
H270.42300.32380.44630.084*
C280.4749 (4)0.3814 (6)0.5310 (6)0.060 (3)
C290.5256 (4)0.3790 (6)0.5769 (5)0.053 (2)
C300.5460 (4)0.4384 (6)0.6284 (5)0.054 (2)
C310.5155 (4)0.5002 (6)0.6345 (6)0.060 (3)
C320.4630 (4)0.4995 (7)0.5871 (7)0.073 (3)
H320.44170.53970.59080.088*
C330.4445 (4)0.4443 (7)0.5394 (7)0.075 (3)
H330.41030.44620.50980.090*
C340.5386 (4)0.5586 (6)0.6846 (6)0.070 (3)
H340.51930.60030.69140.084*
C350.5904 (4)0.5541 (6)0.7243 (6)0.072 (3)
H350.60660.59360.75610.086*
C360.6175 (4)0.4912 (6)0.7162 (6)0.063 (3)
H360.65200.48860.74480.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cr10.0721 (11)0.0780 (13)0.0503 (10)−0.0063 (10)0.0256 (9)−0.0105 (9)
Cr20.0673 (10)0.0675 (11)0.0454 (9)−0.0016 (9)0.0223 (8)−0.0058 (8)
Ni10.0473 (7)0.0651 (8)0.0354 (6)0.0018 (6)0.0123 (5)−0.0019 (6)
N10.051 (4)0.058 (5)0.042 (5)0.001 (4)0.016 (4)0.003 (4)
N20.054 (5)0.058 (6)0.041 (5)0.000 (4)0.013 (4)0.003 (4)
N30.053 (5)0.067 (6)0.043 (5)0.005 (4)0.016 (4)−0.002 (4)
N40.061 (5)0.076 (6)0.046 (5)−0.005 (5)0.019 (4)0.002 (4)
N50.057 (5)0.073 (6)0.043 (5)−0.005 (5)0.013 (4)−0.003 (4)
N60.058 (5)0.069 (6)0.043 (5)0.005 (4)0.019 (4)−0.003 (4)
O10.092 (5)0.115 (6)0.077 (5)0.004 (4)0.049 (4)−0.003 (4)
O20.098 (6)0.171 (8)0.073 (5)0.031 (6)0.004 (5)−0.021 (5)
O30.133 (7)0.097 (6)0.124 (7)−0.032 (5)0.075 (6)−0.032 (5)
O40.078 (4)0.090 (5)0.077 (5)0.006 (4)0.040 (4)−0.002 (4)
O50.084 (5)0.097 (5)0.063 (4)0.005 (4)0.031 (4)0.014 (4)
O60.110 (6)0.071 (5)0.109 (6)0.002 (4)0.055 (5)−0.014 (4)
O70.074 (5)0.104 (6)0.063 (5)−0.007 (4)0.001 (4)−0.005 (4)
O80.119 (7)0.154 (9)0.176 (10)0.007 (6)0.006 (7)−0.031 (7)
O90.088 (10)0.107 (12)0.106 (12)0.001 (9)0.032 (9)−0.014 (10)
O100.122 (14)0.174 (19)0.18 (2)−0.008 (13)0.084 (14)−0.032 (15)
O110.146 (16)0.156 (18)0.18 (2)0.018 (14)0.048 (15)−0.010 (15)
O120.145 (15)0.133 (16)0.143 (17)0.005 (13)0.029 (13)−0.005 (13)
O130.161 (19)0.18 (2)0.21 (2)0.002 (16)0.024 (18)−0.033 (17)
O140.167 (19)0.17 (2)0.21 (2)−0.006 (16)0.019 (18)0.003 (18)
C10.060 (6)0.069 (8)0.049 (6)0.005 (6)0.017 (5)−0.003 (6)
C20.064 (7)0.076 (8)0.060 (7)−0.004 (6)0.013 (6)0.010 (6)
C30.063 (7)0.081 (8)0.049 (6)−0.002 (6)0.023 (5)0.010 (6)
C40.049 (5)0.071 (7)0.044 (6)0.001 (5)0.011 (5)0.006 (6)
C50.046 (5)0.070 (7)0.040 (5)0.002 (5)0.014 (4)−0.003 (5)
C60.065 (7)0.089 (9)0.048 (6)0.002 (6)0.020 (5)−0.002 (6)
C70.073 (7)0.079 (8)0.051 (7)0.000 (6)0.021 (5)−0.014 (6)
C80.054 (6)0.068 (8)0.050 (6)0.004 (5)0.017 (5)−0.003 (6)
C90.048 (6)0.064 (7)0.043 (6)0.003 (5)0.020 (5)0.002 (5)
C100.066 (7)0.075 (8)0.063 (7)0.008 (6)0.012 (6)−0.013 (6)
C110.077 (7)0.066 (8)0.065 (7)0.002 (6)0.011 (6)0.005 (6)
C120.067 (6)0.075 (8)0.050 (6)0.003 (6)0.017 (5)0.004 (6)
C130.064 (7)0.069 (7)0.051 (6)0.004 (6)0.013 (6)−0.003 (5)
C140.069 (7)0.075 (8)0.065 (8)−0.005 (6)−0.001 (6)−0.006 (6)
C150.081 (8)0.072 (8)0.053 (7)0.005 (7)−0.007 (6)−0.009 (6)
C160.078 (7)0.065 (7)0.049 (7)0.009 (6)0.012 (6)−0.004 (5)
C170.063 (6)0.064 (7)0.043 (6)0.010 (6)0.009 (5)−0.006 (5)
C180.065 (7)0.067 (7)0.041 (6)0.010 (6)0.020 (5)0.002 (5)
C190.074 (7)0.066 (7)0.053 (7)0.012 (6)0.023 (6)0.000 (6)
C200.096 (9)0.083 (8)0.048 (7)0.009 (7)0.015 (7)0.001 (6)
C210.096 (9)0.084 (9)0.054 (7)0.007 (7)0.006 (7)−0.004 (6)
C220.091 (8)0.087 (9)0.057 (7)0.020 (7)0.037 (7)0.005 (6)
C230.070 (7)0.090 (8)0.071 (8)0.002 (6)0.029 (7)0.020 (7)
C240.070 (7)0.088 (8)0.057 (7)0.002 (6)0.023 (6)0.004 (6)
C250.065 (7)0.079 (8)0.057 (7)0.001 (6)0.020 (6)0.000 (6)
C260.069 (8)0.092 (9)0.061 (7)−0.013 (7)0.014 (6)0.004 (6)
C270.058 (7)0.092 (9)0.057 (7)−0.003 (7)0.010 (6)0.016 (7)
C280.053 (7)0.075 (8)0.053 (7)0.000 (6)0.019 (6)0.009 (6)
C290.051 (6)0.069 (8)0.043 (6)0.003 (6)0.020 (5)0.006 (5)
C300.056 (7)0.067 (7)0.045 (6)0.004 (6)0.024 (5)0.006 (5)
C310.055 (7)0.074 (8)0.055 (6)0.006 (6)0.023 (6)0.001 (6)
C320.065 (8)0.088 (9)0.072 (8)0.018 (7)0.027 (7)0.007 (7)
C330.060 (7)0.094 (9)0.068 (8)0.008 (7)0.012 (6)0.012 (7)
C340.074 (8)0.081 (8)0.064 (7)0.015 (7)0.033 (6)0.003 (6)
C350.082 (8)0.070 (8)0.065 (7)0.004 (7)0.024 (7)−0.012 (6)
C360.060 (6)0.073 (8)0.058 (7)0.008 (6)0.019 (5)−0.004 (6)

Geometric parameters (Å, °)

Cr1—O31.583 (7)C6—C71.307 (12)
Cr1—O21.587 (7)C6—H60.9300
Cr1—O11.614 (6)C7—C81.440 (12)
Cr1—O41.753 (6)C7—H70.9300
Cr2—O61.593 (7)C8—C91.389 (12)
Cr2—O71.599 (6)C8—C101.398 (13)
Cr2—O51.600 (6)C10—C111.381 (13)
Cr2—O41.786 (6)C10—H100.9300
Ni1—N32.064 (7)C11—C121.370 (12)
Ni1—N22.072 (7)C11—H110.9300
Ni1—N42.084 (7)C12—H120.9300
Ni1—N12.088 (7)C13—C141.411 (12)
Ni1—N62.094 (8)C13—H130.9300
Ni1—N52.115 (7)C14—C151.359 (13)
N1—C11.298 (11)C14—H140.9300
N1—C51.346 (10)C15—C161.375 (13)
N2—C121.310 (11)C15—H150.9300
N2—C91.350 (10)C16—C171.402 (12)
N3—C131.301 (10)C16—C211.426 (14)
N3—C171.361 (11)C17—C181.396 (12)
N4—C241.319 (11)C18—C191.386 (12)
N4—C181.351 (11)C19—C221.395 (13)
N5—C251.332 (11)C19—C201.442 (13)
N5—C291.364 (11)C20—C211.296 (13)
N6—C361.324 (11)C20—H200.9300
N6—C301.391 (10)C21—H210.9300
O8—H8C0.8502C22—C231.353 (13)
O8—H8D0.8500C22—H220.9300
O9—H9C0.8500C23—C241.407 (12)
O9—H9D0.8501C23—H230.9300
O9—H9A0.8500C24—H240.9300
O10—H10C0.8502C25—C261.425 (12)
O10—H10D0.8500C25—H250.9300
O11—H11C0.8500C26—C271.335 (13)
O11—H11D0.8501C26—H260.9300
O12—H12C0.8500C27—C281.388 (13)
O12—H12D0.8500C27—H270.9300
O12—H12A0.8499C28—C291.388 (12)
O13—H13C0.8498C28—C331.416 (13)
O13—H13D0.8498C29—C301.401 (12)
O14—H14C0.8500C30—C311.393 (12)
O14—H14D0.8500C31—C341.393 (13)
C1—C21.405 (12)C31—C321.434 (13)
C1—H10.9300C32—C331.298 (13)
C2—C31.342 (12)C32—H320.9300
C2—H20.9300C33—H330.9300
C3—C41.369 (12)C34—C351.386 (12)
C3—H30.9300C34—H340.9300
C4—C51.404 (11)C35—C361.364 (12)
C4—C61.463 (12)C35—H350.9300
C5—C91.428 (12)C36—H360.9300
O3—Cr1—O2108.4 (5)C8—C9—C5119.3 (8)
O3—Cr1—O1109.5 (4)C11—C10—C8119.8 (10)
O2—Cr1—O1111.4 (4)C11—C10—H10120.1
O3—Cr1—O4109.7 (4)C8—C10—H10120.1
O2—Cr1—O4109.0 (4)C12—C11—C10117.5 (10)
O1—Cr1—O4108.9 (3)C12—C11—H11121.3
O6—Cr2—O7109.6 (4)C10—C11—H11121.3
O6—Cr2—O5110.7 (4)N2—C12—C11125.4 (9)
O7—Cr2—O5108.1 (4)N2—C12—H12117.3
O6—Cr2—O4107.1 (3)C11—C12—H12117.3
O7—Cr2—O4111.3 (3)N3—C13—C14123.3 (10)
O5—Cr2—O4110.1 (3)N3—C13—H13118.4
N3—Ni1—N298.5 (3)C14—C13—H13118.4
N3—Ni1—N479.7 (3)C15—C14—C13117.6 (10)
N2—Ni1—N495.3 (3)C15—C14—H14121.2
N3—Ni1—N195.5 (3)C13—C14—H14121.2
N2—Ni1—N179.1 (3)C14—C15—C16121.5 (10)
N4—Ni1—N1172.1 (3)C14—C15—H15119.3
N3—Ni1—N691.9 (3)C16—C15—H15119.3
N2—Ni1—N6168.5 (3)C15—C16—C17116.9 (10)
N4—Ni1—N691.5 (3)C15—C16—C21124.5 (11)
N1—Ni1—N695.0 (3)C17—C16—C21118.6 (10)
N3—Ni1—N5168.9 (3)N3—C17—C18118.2 (8)
N2—Ni1—N591.5 (3)N3—C17—C16122.5 (9)
N4—Ni1—N594.7 (3)C18—C17—C16119.2 (9)
N1—Ni1—N591.1 (3)N4—C18—C19121.9 (9)
N6—Ni1—N578.6 (3)N4—C18—C17117.2 (9)
C1—N1—C5118.2 (8)C19—C18—C17120.9 (10)
C1—N1—Ni1129.1 (7)C18—C19—C22117.3 (10)
C5—N1—Ni1112.7 (6)C18—C19—C20118.2 (10)
C12—N2—C9116.9 (8)C22—C19—C20124.4 (10)
C12—N2—Ni1129.9 (7)C21—C20—C19121.0 (11)
C9—N2—Ni1112.6 (6)C21—C20—H20119.5
C13—N3—C17118.2 (8)C19—C20—H20119.5
C13—N3—Ni1129.6 (7)C20—C21—C16121.8 (11)
C17—N3—Ni1112.0 (6)C20—C21—H21119.1
C24—N4—C18118.9 (8)C16—C21—H21119.1
C24—N4—Ni1128.9 (7)C23—C22—C19121.7 (10)
C18—N4—Ni1112.3 (6)C23—C22—H22119.1
C25—N5—C29118.3 (8)C19—C22—H22119.1
C25—N5—Ni1128.4 (7)C22—C23—C24116.8 (10)
C29—N5—Ni1113.3 (6)C22—C23—H23121.6
C36—N6—C30117.0 (8)C24—C23—H23121.6
C36—N6—Ni1129.8 (7)N4—C24—C23123.3 (10)
C30—N6—Ni1113.2 (6)N4—C24—H24118.4
Cr1—O4—Cr2131.4 (4)C23—C24—H24118.4
H8C—O8—H8D108.7N5—C25—C26121.4 (10)
H9C—O9—H9D108.3N5—C25—H25119.3
H9C—O9—H9A109.9C26—C25—H25119.3
H9D—O9—H9A109.9C27—C26—C25119.5 (10)
H10C—O10—H10D108.6C27—C26—H26120.3
H11C—O11—H11D107.4C25—C26—H26120.3
H12C—O12—H12D108.8C26—C27—C28120.1 (10)
H12C—O12—H12A110.6C26—C27—H27119.9
H12D—O12—H12A110.6C28—C27—H27119.9
H13C—O13—H13D108.5C29—C28—C27118.5 (10)
H14C—O14—H14D108.3C29—C28—C33118.1 (10)
N1—C1—C2123.0 (9)C27—C28—C33123.4 (11)
N1—C1—H1118.5N5—C29—C28122.1 (9)
C2—C1—H1118.5N5—C29—C30117.6 (9)
C3—C2—C1118.5 (10)C28—C29—C30120.3 (10)
C3—C2—H2120.7N6—C30—C31122.6 (9)
C1—C2—H2120.7N6—C30—C29117.1 (9)
C2—C3—C4120.6 (9)C31—C30—C29120.3 (10)
C2—C3—H3119.7C34—C31—C30117.5 (10)
C4—C3—H3119.7C34—C31—C32125.0 (11)
C3—C4—C5117.3 (9)C30—C31—C32117.4 (10)
C3—C4—C6125.2 (9)C33—C32—C31121.7 (11)
C5—C4—C6117.4 (10)C33—C32—H32119.1
N1—C5—C4122.3 (9)C31—C32—H32119.1
N1—C5—C9116.7 (8)C32—C33—C28122.1 (11)
C4—C5—C9120.9 (9)C32—C33—H33118.9
C7—C6—C4121.0 (10)C28—C33—H33118.9
C7—C6—H6119.5C35—C34—C31119.5 (10)
C4—C6—H6119.5C35—C34—H34120.3
C6—C7—C8122.3 (10)C31—C34—H34120.3
C6—C7—H7118.9C36—C35—C34119.5 (10)
C8—C7—H7118.9C36—C35—H35120.3
C9—C8—C10117.0 (9)C34—C35—H35120.3
C9—C8—C7119.0 (9)N6—C36—C35123.9 (10)
C10—C8—C7124.0 (10)N6—C36—H36118.0
N2—C9—C8123.5 (9)C35—C36—H36118.0
N2—C9—C5117.1 (8)
N3—Ni1—N1—C1−74.9 (8)C10—C8—C9—N21.3 (13)
N2—Ni1—N1—C1−172.5 (8)C7—C8—C9—N2−177.8 (8)
N4—Ni1—N1—C1−127 (2)C10—C8—C9—C5178.2 (8)
N6—Ni1—N1—C117.4 (8)C7—C8—C9—C5−0.9 (13)
N5—Ni1—N1—C196.1 (8)N1—C5—C9—N2−3.0 (11)
N3—Ni1—N1—C5107.9 (6)C4—C5—C9—N2176.4 (7)
N2—Ni1—N1—C510.3 (5)N1—C5—C9—C8179.9 (7)
N4—Ni1—N1—C556 (2)C4—C5—C9—C8−0.7 (13)
N6—Ni1—N1—C5−159.8 (6)C9—C8—C10—C11−1.9 (13)
N5—Ni1—N1—C5−81.1 (6)C7—C8—C10—C11177.2 (9)
N3—Ni1—N2—C1283.5 (8)C8—C10—C11—C120.5 (14)
N4—Ni1—N2—C123.2 (8)C9—N2—C12—C11−2.5 (13)
N1—Ni1—N2—C12177.5 (8)Ni1—N2—C12—C11167.9 (7)
N6—Ni1—N2—C12−122.6 (15)C10—C11—C12—N21.9 (15)
N5—Ni1—N2—C12−91.7 (8)C17—N3—C13—C14−0.6 (14)
N3—Ni1—N2—C9−105.8 (6)Ni1—N3—C13—C14173.6 (7)
N4—Ni1—N2—C9173.9 (6)N3—C13—C14—C15−0.9 (15)
N1—Ni1—N2—C9−11.8 (6)C13—C14—C15—C161.9 (15)
N6—Ni1—N2—C948.2 (17)C14—C15—C16—C17−1.4 (15)
N5—Ni1—N2—C979.0 (6)C14—C15—C16—C21−179.8 (10)
N2—Ni1—N3—C1384.9 (8)C13—N3—C17—C18−178.6 (8)
N4—Ni1—N3—C13178.7 (8)Ni1—N3—C17—C186.3 (10)
N1—Ni1—N3—C135.1 (8)C13—N3—C17—C161.1 (13)
N6—Ni1—N3—C13−90.1 (8)Ni1—N3—C17—C16−174.0 (7)
N5—Ni1—N3—C13−121.0 (16)C15—C16—C17—N3−0.2 (14)
N2—Ni1—N3—C17−100.7 (6)C21—C16—C17—N3178.3 (9)
N4—Ni1—N3—C17−6.8 (6)C15—C16—C17—C18179.5 (9)
N1—Ni1—N3—C17179.5 (6)C21—C16—C17—C18−2.0 (14)
N6—Ni1—N3—C1784.3 (6)C24—N4—C18—C19−4.1 (13)
N5—Ni1—N3—C1753.5 (19)Ni1—N4—C18—C19175.1 (7)
N3—Ni1—N4—C24−174.3 (9)C24—N4—C18—C17175.5 (8)
N2—Ni1—N4—C24−76.7 (8)Ni1—N4—C18—C17−5.3 (10)
N1—Ni1—N4—C24−122 (2)N3—C17—C18—N4−0.6 (13)
N6—Ni1—N4—C2494.0 (8)C16—C17—C18—N4179.7 (8)
N5—Ni1—N4—C2415.3 (8)N3—C17—C18—C19179.0 (8)
N3—Ni1—N4—C186.6 (6)C16—C17—C18—C19−0.7 (14)
N2—Ni1—N4—C18104.2 (6)N4—C18—C19—C224.7 (14)
N1—Ni1—N4—C1859 (3)C17—C18—C19—C22−174.8 (9)
N6—Ni1—N4—C18−85.1 (6)N4—C18—C19—C20−178.9 (8)
N5—Ni1—N4—C18−163.8 (6)C17—C18—C19—C201.6 (14)
N3—Ni1—N5—C25−151.4 (15)C18—C19—C20—C210.5 (15)
N2—Ni1—N5—C253.0 (8)C22—C19—C20—C21176.6 (10)
N4—Ni1—N5—C25−92.4 (8)C19—C20—C21—C16−3.3 (17)
N1—Ni1—N5—C2582.2 (8)C15—C16—C21—C20−177.5 (10)
N6—Ni1—N5—C25177.0 (8)C17—C16—C21—C204.1 (16)
N3—Ni1—N5—C2928.3 (19)C18—C19—C22—C23−2.0 (15)
N2—Ni1—N5—C29−177.3 (6)C20—C19—C22—C23−178.2 (9)
N4—Ni1—N5—C2987.3 (6)C19—C22—C23—C24−1.1 (15)
N1—Ni1—N5—C29−98.1 (6)C18—N4—C24—C230.6 (14)
N6—Ni1—N5—C29−3.3 (6)Ni1—N4—C24—C23−178.4 (7)
N3—Ni1—N6—C368.1 (8)C22—C23—C24—N41.9 (15)
N2—Ni1—N6—C36−146.1 (13)C29—N5—C25—C261.1 (13)
N4—Ni1—N6—C3687.8 (8)Ni1—N5—C25—C26−179.2 (6)
N1—Ni1—N6—C36−87.6 (8)N5—C25—C26—C27−1.9 (14)
N5—Ni1—N6—C36−177.7 (8)C25—C26—C27—C280.9 (14)
N3—Ni1—N6—C30−170.3 (6)C26—C27—C28—C290.7 (14)
N2—Ni1—N6—C3035.4 (18)C26—C27—C28—C33179.3 (9)
N4—Ni1—N6—C30−90.6 (6)C25—N5—C29—C280.6 (12)
N1—Ni1—N6—C3094.0 (6)Ni1—N5—C29—C28−179.2 (6)
N5—Ni1—N6—C303.9 (6)C25—N5—C29—C30−178.1 (8)
O3—Cr1—O4—Cr227.0 (7)Ni1—N5—C29—C302.1 (9)
O2—Cr1—O4—Cr2−91.5 (6)C27—C28—C29—N5−1.5 (13)
O1—Cr1—O4—Cr2146.8 (5)C33—C28—C29—N5179.9 (8)
O6—Cr2—O4—Cr1159.5 (5)C27—C28—C29—C30177.2 (8)
O7—Cr2—O4—Cr1−80.7 (6)C33—C28—C29—C30−1.5 (13)
O5—Cr2—O4—Cr139.1 (6)C36—N6—C30—C31−0.6 (12)
C5—N1—C1—C22.4 (13)Ni1—N6—C30—C31178.0 (7)
Ni1—N1—C1—C2−174.6 (6)C36—N6—C30—C29177.3 (8)
N1—C1—C2—C3−0.2 (14)Ni1—N6—C30—C29−4.1 (9)
C1—C2—C3—C4−0.3 (14)N5—C29—C30—N61.3 (11)
C2—C3—C4—C5−1.4 (13)C28—C29—C30—N6−177.4 (7)
C2—C3—C4—C6−178.0 (8)N5—C29—C30—C31179.2 (8)
C1—N1—C5—C4−4.3 (12)C28—C29—C30—C310.5 (13)
Ni1—N1—C5—C4173.3 (6)N6—C30—C31—C340.1 (13)
C1—N1—C5—C9175.2 (8)C29—C30—C31—C34−177.8 (8)
Ni1—N1—C5—C9−7.3 (9)N6—C30—C31—C32178.5 (8)
C3—C4—C5—N13.8 (13)C29—C30—C31—C320.7 (13)
C6—C4—C5—N1−179.4 (7)C34—C31—C32—C33177.4 (10)
C3—C4—C5—C9−175.6 (8)C30—C31—C32—C33−1.0 (14)
C6—C4—C5—C91.2 (12)C31—C32—C33—C280.0 (16)
C3—C4—C6—C7176.4 (9)C29—C28—C33—C321.2 (15)
C5—C4—C6—C7−0.1 (13)C27—C28—C33—C32−177.3 (10)
C4—C6—C7—C8−1.5 (15)C30—C31—C34—C351.6 (14)
C6—C7—C8—C92.0 (14)C32—C31—C34—C35−176.8 (9)
C6—C7—C8—C10−177.0 (9)C31—C34—C35—C36−2.7 (15)
C12—N2—C9—C80.8 (13)C30—N6—C36—C35−0.5 (13)
Ni1—N2—C9—C8−171.3 (7)Ni1—N6—C36—C35−178.9 (7)
C12—N2—C9—C5−176.2 (7)C34—C35—C36—N62.2 (15)
Ni1—N2—C9—C511.8 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O14—H14D···O10i0.852.062.91 (3)177
O14—H14C···O10ii0.851.752.60 (3)176
O13—H13D···O140.851.762.61 (3)179
O13—H13C···O2iii0.851.982.83 (2)176
O12—H12D···O9iv0.852.162.99 (2)165
O12—H12C···O140.852.112.93 (3)165
O10—H10D···O110.851.932.78 (3)171
O10—H10C···O10.851.912.751 (17)172
O9—H9A···O12v0.852.242.99 (2)147
O9—H9D···O9vi0.851.942.78 (3)176
O9—H9C···O80.852.112.962 (17)177
O8—H8D···O11vii0.851.922.76 (2)167
O8—H8C···O60.852.002.836 (11)168

Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) x−1/2, y−1/2, z; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x, −y+1, z−1/2; (v) x, −y+1, z+1/2; (vi) −x+1, y, −z+3/2; (vii) −x+3/2, −y+3/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2680).

References

  • Bruker (2000). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ejsmont, K., Wasielewski, M. & Zaleski, J. (2002). Acta Cryst. E58, m200–m202.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Suescun, L., Mombrú, A. W. & Mariezcurrena, R. A. (1999). Acta Cryst. C55, 1991–1993.
  • Wang, J.-J., Li, D.-S., Tang, L., Fu, F., Guo, L. & Zhang, Z.-L. (2007). Z. Kristallogr. New Cryst. Struct.222, 61–63.
  • Wiehl, L., Schreuer, J. & Haussuhl, E. (2008). Z. Kristallogr. New Cryst. Struct.223, 82–84.

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