metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Poly[[bis­­[μ2-1,2-bis­­(pyridin-4-yl)ethene-κ2N:N′]bis­­(thio­cyanato-κN)cobalt(II)] 1,2-bis­­(pyridin-4-yl)ethene monosolvate dihydrate]

aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth-Strasse 2, 24118 Kiel, Germany
*Correspondence e-mail: swoehlert@ac.uni-kiel.de

(Received 25 July 2013; accepted 29 July 2013; online 10 August 2013)

The asymmetric unit of the title compound, {[Co(NCS)2(C12H10N2)2]·C12H10N2·2H2O}n, consists of two independent CoII cations, four distinct thio­cyanate anions, six 1,2-bis­(pyridin-4-yl)ethene (4-bpe) mol­ecules and four lattice water mol­ecules. The CoII cations are each coordinated by two N-bonded thio­cyanate anions and four 4-bpe ligands within a slightly distorted CoN6 octa­hedron. The two independent CoII cations are linked by the 4-bpe ligands into two distinct layers, parallel to the ac and bc planes, that inter­penetrate. From this arrangement, channels are formed in which non-coordinated 4-bpe and lattice water mol­ecules are hydrogen-bonded into chains that elongate in the c-axis direction.

Related literature

For the background to this work, see: Wöhlert et al. (2011[Wöhlert, S., Boeckmann, J., Wriedt, M. & Näther, C. (2011). Angew. Chem. Int. Ed. 50, 6920-6923.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(NCS)2(C12H10N2)2]·C12H10N2·2H2O

  • Mr = 757.78

  • Orthorhombic, P n n 2

  • a = 22.3698 (11) Å

  • b = 22.4296 (16) Å

  • c = 15.3707 (7) Å

  • V = 7712.2 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.60 mm−1

  • T = 170 K

  • 0.09 × 0.05 × 0.03 mm

Data collection
  • Stoe IPDS-1 diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe, 2008[Stoe (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.849, Tmax = 0.971

  • 34972 measured reflections

  • 9556 independent reflections

  • 7608 reflections with I > 2σ(I)

  • Rint = 0.054

  • θmax = 22.4°

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.108

  • S = 1.04

  • 9556 reflections

  • 919 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.35 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4369 Friedel pairs

  • Absolute structure parameter: 0.06 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H2O1⋯O3 0.84 2.00 2.825 (8) 169
O2—H2O2⋯O4 0.84 2.09 2.818 (8) 144
O3—H2O3⋯N91 0.84 2.15 2.933 (9) 156
O4—H1O4⋯N110 0.84 2.14 2.885 (9) 148
O1—H1O1⋯N90i 0.84 2.07 2.877 (10) 160
O2—H1O2⋯N111ii 0.84 2.03 2.858 (10) 170
O4—H2O4⋯O2iii 0.84 2.10 2.844 (8) 147
Symmetry codes: (i) -x+2, -y+1, z-1; (ii) x, y, z+1; (iii) -x+1, -y+1, z.

Data collection: X-AREA (Stoe, 2008[Stoe (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2011[Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In our ongoing project on the synthesis, structures and properties of coordination polymers based on transition metal(II) thio- and selenocyanates we investigated compounds with 1,2-bis(pyridin-4-yl)ethene (4-bpe) as co-ligand (Wöhlert et al., 2011). In the course of these investigations crystals of the title compound were obtained that were characterized by single-crystal X-ray diffraction.

The asymmetric unit of the title compound consists of two crystallographic independent cobalt(II) cations (Co1 and Co2), four distinct thiocyanato anions, six 4-bpe ligands and four water molecules (Figs. 1–3). Each cobalt cation is coordinated by two N-bonded thiocyanato anions and four 1,2-bis(4-pyridin-4-yl)ethene (4-bpe) ligands within slightly distorted octahedra. The CoN6 distances ranges from 2.067 (4) Å to 2.185 (5) Å with angles around the cobalt(II) cations between 87.46 (16) to 93.77 (18)° and 176.95 (16) to 179.22 (18)°. In the crystal structure the cobalt(II) cations are linked by the 4-bpe ligands into layers. There are two kinds of layers. Those based on Co1 are parallel to the a/c-plane, whereas those based on Co2 parallel to the b/c-plane. These layers interpenetrate to form channels that elongate along the c-axis. Within these channels additional non-coordinating 4-bpe ligands and water molecules are embedded that are hydrogen bonded into chains (Table 1).

Related literature top

For the background to this work, see: Wöhlert et al. (2011).

Experimental top

Co(NCS)2 and 1,2-bis(pyridin-4-yl)ethene were obtained from Alfa Aesar and Sigma Aldrich. All chemicals were used without further purification. 0.15 mmol (28 mg) Co(NCS)2 and 0.6 mmol (108 mg) 1,2-bis(pyridin-4-yl)ethene were reacted in 1 ml H2O in a closed test-tube at 120 °C for three days. On cooling red block-shaped single crystals of the title compound were obtained.

Refinement top

All H atoms were positions with idealized geometry and were refined isotropic with Uiso(H) = 1.2 Ueq(C) using a riding model with C—H = 0.95 Å. The O—H hydrogen atoms were located in a difference map, their bond lengths were set to ideal values of 0.84 Å and finally they were refined with Uiso(H) = 1.5 Ueq(O) using a riding model. The absolute structure was determined on the basis of 4369 Friedel pairs. Because of the large unit-cell parameters and the relatively large width of the reflection profiles diffraction data were measured to theta of only 22.4°

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Environment of Co1 with labeling and displacement ellipsoids drawn at the 50% probability level. [Symmetry codes: (i) x - 1/2, -y + 1/2, z + 1/2; (ii) x + 1/2, - y + 1/2, z + 1/2.]
[Figure 2] Fig. 2. Environment of Co2 with labeling and displacement ellipsoids drawn at the 50% probability level. [Symmetry codes: (iii) -x - 3/2, y - 1/2, z - 1/2; (iv) -x + 3/2, y - 1/2, z + 1/2.]
[Figure 3] Fig. 3. View of the non-coordinated 1,2-bis(pyridin-4-yl)ethene ligands and the water molecules with labeling and displacement ellipsoids drawn at the 50% probability level.
[Figure 4] Fig. 4. Crystal structure of the title compound with view along the c-axis (orange = cobalt, blue = nitrogen, yellow = sulfur, grey = carbon, white = hydrogen).
Poly[[bis[µ2-1,2-bis(pyridin-4-yl)ethene-κ2N:N']bis(thiocyanato-κN)cobalt(II)] 1,2-bis(pyridin-4-yl)ethene monosolvate dihydrate] top
Crystal data top
[Co(NCS)2(C12H10N2)2]·C12H10N2·2H2OF(000) = 3144
Mr = 757.78Dx = 1.305 Mg m3
Orthorhombic, Pnn2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 -2nCell parameters from 34972 reflections
a = 22.3698 (11) Åθ = 1.6–22.4°
b = 22.4296 (16) ŵ = 0.60 mm1
c = 15.3707 (7) ÅT = 170 K
V = 7712.2 (8) Å3Block, red
Z = 80.09 × 0.05 × 0.03 mm
Data collection top
Stoe IPDS-1
diffractometer
9556 independent reflections
Radiation source: fine-focus sealed tube7608 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ scanθmax = 22.4°, θmin = 1.6°
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe, 2008)
h = 2324
Tmin = 0.849, Tmax = 0.971k = 2424
34972 measured reflectionsl = 1516
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0477P)2 + 5.5114P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
9556 reflectionsΔρmax = 0.23 e Å3
919 parametersΔρmin = 0.35 e Å3
1 restraintAbsolute structure: Flack (1983), 4369 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (2)
Crystal data top
[Co(NCS)2(C12H10N2)2]·C12H10N2·2H2OV = 7712.2 (8) Å3
Mr = 757.78Z = 8
Orthorhombic, Pnn2Mo Kα radiation
a = 22.3698 (11) ŵ = 0.60 mm1
b = 22.4296 (16) ÅT = 170 K
c = 15.3707 (7) Å0.09 × 0.05 × 0.03 mm
Data collection top
Stoe IPDS-1
diffractometer
9556 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe, 2008)
7608 reflections with I > 2σ(I)
Tmin = 0.849, Tmax = 0.971Rint = 0.054
34972 measured reflectionsθmax = 22.4°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.108Δρmax = 0.23 e Å3
S = 1.04Δρmin = 0.35 e Å3
9556 reflectionsAbsolute structure: Flack (1983), 4369 Friedel pairs
919 parametersAbsolute structure parameter: 0.06 (2)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.74806 (2)0.26235 (3)1.03062 (6)0.02261 (17)
Co20.75553 (3)0.23789 (2)1.04067 (5)0.02213 (17)
N10.74285 (18)0.1698 (2)1.0203 (3)0.0334 (12)
C10.7421 (2)0.1186 (3)1.0282 (4)0.0347 (13)
S10.74027 (11)0.04599 (6)1.03888 (18)0.0737 (6)
N20.75022 (18)0.35535 (18)1.0409 (4)0.0316 (9)
C20.7492 (2)0.40689 (19)1.0366 (4)0.0254 (10)
S20.74847 (9)0.47821 (6)1.02980 (16)0.0560 (4)
N30.66189 (19)0.24203 (17)1.0426 (4)0.0324 (10)
C30.6104 (2)0.2494 (2)1.0418 (4)0.0284 (12)
S30.53951 (6)0.26009 (11)1.03899 (18)0.0754 (6)
N40.84792 (18)0.23491 (18)1.0373 (4)0.0335 (10)
C40.8991 (2)0.2401 (2)1.0385 (4)0.0296 (12)
S40.97128 (6)0.24874 (8)1.03817 (17)0.0605 (5)
N100.8173 (2)0.2646 (2)0.9323 (3)0.0276 (12)
C100.8632 (2)0.3026 (3)0.9388 (4)0.0322 (14)
H100.86020.33460.97890.039*
C110.9143 (2)0.2974 (3)0.8904 (4)0.0330 (15)
H110.94620.32480.89860.040*
C120.9197 (3)0.2517 (3)0.8285 (4)0.0294 (14)
C130.8705 (3)0.2140 (3)0.8203 (4)0.0377 (15)
H130.87140.18260.77890.045*
C140.8213 (2)0.2215 (3)0.8708 (4)0.0331 (14)
H140.78820.19550.86270.040*
C150.9730 (3)0.2412 (3)0.7771 (5)0.0416 (17)
H150.96990.21450.72940.050*
C161.0256 (2)0.2660 (3)0.7918 (5)0.0353 (14)
H161.02920.29240.83990.042*
C171.0791 (2)0.2553 (3)0.7377 (4)0.0288 (13)
C181.1289 (2)0.2931 (3)0.7447 (4)0.0336 (14)
H181.12900.32430.78650.040*
C191.1784 (3)0.2850 (3)0.6902 (4)0.0342 (15)
H191.21110.31190.69400.041*
C201.1344 (2)0.2022 (2)0.6300 (4)0.0311 (14)
H201.13690.16950.59100.037*
C211.0843 (2)0.2080 (2)0.6797 (4)0.0288 (14)
H211.05290.17970.67470.035*
N111.1806 (2)0.2407 (2)0.6334 (3)0.0256 (11)
N300.6761 (2)0.2686 (2)0.9370 (3)0.0265 (12)
C300.6315 (2)0.2294 (2)0.9442 (4)0.0307 (14)
H300.63540.19770.98490.037*
C310.5796 (2)0.2328 (3)0.8950 (4)0.0295 (14)
H310.54840.20460.90310.035*
C320.5738 (2)0.2772 (3)0.8344 (4)0.0279 (13)
C330.6202 (2)0.3179 (3)0.8254 (4)0.0327 (14)
H330.61780.34920.78400.039*
C340.6705 (2)0.3119 (3)0.8781 (4)0.0283 (14)
H340.70210.33980.87180.034*
C350.5200 (2)0.2831 (2)0.7799 (4)0.0321 (13)
H350.52120.31040.73270.038*
C360.4699 (2)0.2524 (3)0.7928 (5)0.0334 (15)
H360.46820.22780.84310.040*
C370.4169 (3)0.2531 (2)0.7362 (4)0.0306 (15)
C380.3736 (2)0.2096 (2)0.7459 (4)0.0324 (13)
H380.37700.18090.79100.039*
C390.3252 (2)0.2082 (3)0.6894 (4)0.0304 (14)
H390.29610.17780.69670.037*
C400.3598 (2)0.2911 (2)0.6183 (4)0.0314 (14)
H400.35490.32030.57400.038*
C410.4089 (2)0.2953 (2)0.6713 (4)0.0297 (14)
H410.43700.32660.66370.036*
N310.3177 (2)0.2478 (2)0.6253 (3)0.0276 (12)
N500.7533 (2)0.1692 (2)1.1388 (3)0.0286 (12)
C500.7075 (3)0.1619 (2)1.1948 (4)0.0321 (15)
H500.67900.19311.19960.039*
C510.6994 (3)0.1122 (2)1.2451 (4)0.0330 (14)
H510.66590.10941.28280.040*
C520.7406 (3)0.0659 (2)1.2405 (4)0.0303 (15)
C530.7884 (3)0.0727 (2)1.1856 (4)0.0358 (15)
H530.81800.04241.18160.043*
C540.7935 (3)0.1243 (2)1.1358 (4)0.0310 (14)
H540.82680.12811.09790.037*
C550.7300 (3)0.0120 (2)1.2907 (5)0.0346 (15)
H550.69790.01241.33120.042*
C560.7619 (3)0.0377 (2)1.2841 (5)0.0319 (13)
H560.79280.03841.24180.038*
C570.7533 (3)0.0918 (3)1.3371 (4)0.0278 (14)
C580.7057 (2)0.0992 (2)1.3930 (4)0.0279 (13)
H580.67550.06961.39650.033*
C590.7020 (3)0.1506 (2)1.4447 (4)0.0313 (14)
H590.66920.15481.48340.038*
C600.7886 (3)0.1875 (2)1.3839 (4)0.0309 (14)
H600.81780.21821.37990.037*
C610.7942 (3)0.1382 (2)1.3309 (4)0.0295 (13)
H610.82600.13601.29010.035*
N510.7432 (2)0.1940 (2)1.4414 (3)0.0253 (11)
N700.7484 (2)0.1683 (2)0.9427 (3)0.0250 (11)
C700.7095 (3)0.1230 (2)0.9541 (4)0.0311 (14)
H700.68150.12581.00030.037*
C710.7083 (2)0.0737 (2)0.9029 (4)0.0267 (13)
H710.68080.04240.91460.032*
C720.7477 (3)0.0694 (3)0.8331 (4)0.0336 (16)
C730.7863 (3)0.1166 (3)0.8190 (4)0.0339 (15)
H730.81290.11620.77090.041*
C740.7859 (3)0.1653 (2)0.8765 (4)0.0334 (15)
H740.81330.19700.86750.040*
C750.7502 (3)0.0165 (2)0.7759 (5)0.0321 (16)
H750.76900.02080.72090.039*
C760.7277 (3)0.0368 (2)0.7965 (5)0.0361 (15)
H760.70670.04050.85000.043*
C770.7334 (3)0.0901 (3)0.7416 (4)0.0278 (14)
C780.6960 (3)0.1386 (2)0.7543 (4)0.0341 (15)
H780.66700.13830.79950.041*
C790.7017 (3)0.1882 (3)0.6995 (4)0.0348 (15)
H790.67550.22110.70780.042*
C800.7796 (2)0.1444 (2)0.6259 (4)0.0294 (14)
H800.80920.14640.58170.035*
C810.7763 (3)0.0937 (2)0.6770 (4)0.0314 (14)
H810.80330.06170.66780.038*
N710.7421 (2)0.19110 (19)0.6365 (3)0.0274 (12)
N900.9622 (4)0.5853 (3)0.6652 (5)0.078 (2)
C900.9232 (5)0.5839 (4)0.5997 (7)0.083 (3)
H900.88160.58490.61240.100*
C910.9417 (4)0.5811 (3)0.5125 (6)0.071 (2)
H910.91310.57880.46690.085*
C921.0029 (4)0.5817 (3)0.4937 (6)0.070 (3)
C931.0415 (5)0.5825 (4)0.5614 (6)0.093 (3)
H931.08340.58230.55170.112*
C941.0188 (5)0.5837 (5)0.6452 (7)0.102 (3)
H941.04670.58340.69180.123*
C951.0271 (4)0.5785 (4)0.4014 (7)0.078 (3)
H951.06900.57270.39570.094*
C960.9982 (4)0.5825 (3)0.3325 (6)0.064 (2)
H960.95640.58900.33690.077*
C971.0247 (3)0.5778 (3)0.2423 (5)0.0526 (18)
C980.9905 (4)0.5977 (4)0.1744 (6)0.078 (2)
H980.95210.61450.18420.093*
C991.0135 (4)0.5925 (4)0.0903 (6)0.083 (3)
H990.98910.60540.04340.100*
C1001.0998 (4)0.5517 (4)0.1381 (7)0.069 (2)
H1001.13820.53530.12650.083*
C1011.0804 (4)0.5545 (3)0.2233 (6)0.066 (2)
H1011.10540.54050.26890.079*
N911.0670 (3)0.5709 (3)0.0715 (5)0.0666 (18)
N1100.5768 (3)0.4377 (3)0.4991 (5)0.0718 (19)
C1100.5986 (4)0.4907 (5)0.4782 (7)0.092 (3)
H1100.61310.51510.52410.111*
C1110.6016 (4)0.5132 (4)0.3949 (6)0.082 (3)
H1110.61830.55150.38480.098*
C1120.5807 (3)0.4802 (4)0.3272 (5)0.059 (2)
C1130.5584 (4)0.4241 (4)0.3453 (6)0.071 (2)
H1130.54430.39930.29960.085*
C1140.5566 (4)0.4041 (4)0.4320 (6)0.073 (2)
H1140.54060.36570.44390.087*
C1150.5834 (3)0.5061 (4)0.2376 (7)0.072 (2)
H1150.59100.54760.23310.087*
C1160.5764 (4)0.4776 (4)0.1677 (7)0.076 (3)
H1160.56840.43620.17330.091*
C1170.5792 (3)0.5015 (4)0.0763 (6)0.068 (2)
C1180.5797 (3)0.5619 (4)0.0584 (5)0.068 (2)
H1180.57970.59030.10420.081*
C1190.5803 (4)0.5808 (4)0.0309 (6)0.072 (2)
H1190.57980.62230.04320.087*
C1200.5804 (4)0.4843 (5)0.0766 (6)0.079 (3)
H1200.58070.45620.12280.095*
C1210.5790 (4)0.4635 (4)0.0068 (7)0.084 (3)
H1210.57780.42170.01680.101*
N1110.5815 (3)0.5428 (3)0.0968 (5)0.0731 (19)
O11.0450 (3)0.4249 (2)0.1485 (4)0.0807 (17)
H1O11.05160.41880.20150.121*
H2O11.05060.46050.13350.121*
O20.5698 (2)0.5514 (2)0.7185 (4)0.0801 (17)
H1O20.57400.55330.77270.120*
H2O20.58150.51650.70810.120*
O31.0756 (3)0.5449 (3)0.1151 (4)0.0800 (18)
H1O31.11300.54810.11650.120*
H2O31.06210.55130.06500.120*
O40.5535 (3)0.4292 (2)0.6832 (4)0.0746 (17)
H1O40.56300.41700.63350.112*
H2O40.51650.42710.67430.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0163 (3)0.0301 (3)0.0215 (4)0.0034 (3)0.0018 (4)0.0021 (4)
Co20.0295 (3)0.0160 (3)0.0209 (4)0.0024 (3)0.0006 (4)0.0022 (4)
N10.026 (2)0.039 (3)0.035 (3)0.007 (2)0.003 (2)0.000 (2)
C10.027 (3)0.058 (4)0.019 (3)0.007 (3)0.002 (3)0.002 (3)
S10.1349 (17)0.0268 (8)0.0595 (11)0.0010 (10)0.0109 (15)0.0057 (11)
N20.0234 (19)0.041 (3)0.031 (3)0.008 (2)0.001 (3)0.002 (3)
C20.032 (2)0.020 (3)0.024 (3)0.010 (2)0.002 (3)0.002 (3)
S20.0806 (10)0.0353 (8)0.0520 (11)0.0042 (8)0.0020 (11)0.0065 (10)
N30.047 (3)0.022 (2)0.028 (3)0.0009 (19)0.004 (3)0.001 (2)
C30.028 (3)0.035 (3)0.022 (3)0.005 (2)0.004 (3)0.002 (3)
S30.0335 (8)0.1385 (17)0.0543 (13)0.0099 (10)0.0016 (12)0.0021 (14)
N40.032 (2)0.031 (2)0.038 (3)0.0063 (19)0.007 (3)0.001 (2)
C40.044 (3)0.024 (3)0.021 (3)0.002 (2)0.005 (4)0.004 (3)
S40.0302 (7)0.0890 (13)0.0623 (12)0.0098 (7)0.0049 (12)0.0077 (12)
N100.017 (3)0.037 (3)0.029 (3)0.000 (2)0.002 (2)0.001 (2)
C100.027 (3)0.038 (3)0.032 (4)0.002 (3)0.002 (3)0.001 (3)
C110.018 (3)0.042 (4)0.039 (4)0.004 (3)0.007 (3)0.000 (3)
C120.024 (4)0.050 (4)0.014 (3)0.001 (3)0.000 (3)0.002 (3)
C130.032 (3)0.051 (4)0.030 (4)0.001 (3)0.006 (3)0.008 (3)
C140.026 (3)0.045 (4)0.029 (4)0.008 (3)0.001 (3)0.000 (3)
C150.047 (4)0.051 (4)0.027 (4)0.002 (3)0.003 (4)0.007 (3)
C160.032 (3)0.050 (4)0.024 (3)0.010 (3)0.004 (3)0.004 (3)
C170.024 (3)0.035 (3)0.027 (4)0.006 (3)0.003 (3)0.005 (3)
C180.030 (3)0.047 (4)0.024 (3)0.004 (3)0.003 (3)0.007 (3)
C190.031 (3)0.043 (4)0.029 (4)0.006 (3)0.006 (3)0.004 (3)
C200.025 (3)0.035 (3)0.034 (4)0.005 (3)0.003 (3)0.004 (3)
C210.022 (3)0.024 (3)0.041 (4)0.002 (2)0.008 (3)0.003 (3)
N110.021 (3)0.033 (3)0.022 (3)0.003 (2)0.004 (2)0.002 (2)
N300.016 (3)0.040 (3)0.024 (3)0.000 (2)0.003 (2)0.002 (2)
C300.033 (3)0.029 (3)0.030 (4)0.005 (3)0.002 (3)0.009 (3)
C310.012 (3)0.044 (4)0.032 (4)0.003 (2)0.007 (2)0.002 (3)
C320.020 (3)0.039 (3)0.025 (3)0.001 (3)0.008 (3)0.004 (3)
C330.031 (3)0.044 (4)0.023 (3)0.002 (3)0.011 (3)0.008 (3)
C340.012 (3)0.041 (3)0.031 (4)0.002 (2)0.000 (2)0.005 (3)
C350.023 (3)0.044 (3)0.029 (3)0.000 (2)0.010 (3)0.002 (3)
C360.022 (3)0.043 (4)0.035 (4)0.006 (2)0.009 (3)0.001 (3)
C370.025 (4)0.031 (3)0.036 (4)0.004 (3)0.005 (3)0.001 (3)
C380.032 (3)0.044 (4)0.021 (3)0.002 (3)0.002 (3)0.005 (3)
C390.025 (3)0.031 (3)0.036 (4)0.004 (2)0.003 (3)0.003 (3)
C400.039 (3)0.027 (3)0.028 (4)0.002 (3)0.007 (3)0.006 (3)
C410.017 (3)0.034 (3)0.039 (4)0.009 (2)0.011 (3)0.001 (3)
N310.028 (3)0.026 (3)0.028 (3)0.004 (2)0.002 (2)0.001 (2)
N500.039 (3)0.023 (3)0.024 (3)0.006 (2)0.001 (2)0.003 (2)
C500.041 (4)0.026 (3)0.029 (4)0.009 (3)0.005 (3)0.005 (3)
C510.044 (3)0.027 (3)0.028 (3)0.012 (3)0.010 (3)0.005 (3)
C520.053 (4)0.014 (3)0.024 (3)0.001 (3)0.001 (3)0.008 (3)
C530.051 (4)0.016 (3)0.041 (4)0.006 (3)0.001 (3)0.001 (3)
C540.036 (3)0.022 (3)0.035 (4)0.005 (2)0.001 (3)0.002 (3)
C550.041 (4)0.034 (4)0.029 (3)0.001 (3)0.003 (4)0.012 (3)
C560.042 (3)0.028 (3)0.026 (3)0.003 (3)0.008 (3)0.007 (3)
C570.038 (4)0.028 (3)0.018 (3)0.003 (3)0.001 (3)0.002 (2)
C580.038 (3)0.019 (3)0.027 (4)0.000 (2)0.001 (3)0.006 (2)
C590.038 (3)0.034 (4)0.022 (4)0.008 (3)0.000 (3)0.001 (3)
C600.039 (3)0.020 (3)0.033 (4)0.008 (2)0.003 (3)0.007 (3)
C610.046 (3)0.028 (3)0.015 (3)0.000 (3)0.003 (3)0.005 (3)
N510.036 (3)0.021 (3)0.019 (3)0.006 (2)0.001 (2)0.0029 (19)
N700.033 (3)0.020 (3)0.023 (3)0.004 (2)0.002 (2)0.0025 (19)
C700.037 (3)0.032 (4)0.024 (4)0.003 (3)0.003 (3)0.003 (3)
C710.035 (3)0.014 (3)0.031 (4)0.004 (2)0.002 (3)0.007 (2)
C720.044 (4)0.033 (4)0.023 (3)0.003 (3)0.005 (3)0.008 (3)
C730.044 (3)0.034 (3)0.024 (4)0.007 (3)0.008 (3)0.006 (2)
C740.053 (4)0.014 (3)0.033 (4)0.001 (3)0.002 (3)0.003 (3)
C750.044 (3)0.030 (3)0.022 (4)0.005 (3)0.000 (3)0.010 (3)
C760.049 (4)0.023 (3)0.036 (4)0.005 (3)0.005 (3)0.011 (3)
C770.034 (3)0.029 (4)0.020 (3)0.005 (3)0.000 (3)0.004 (3)
C780.047 (4)0.027 (3)0.028 (4)0.004 (3)0.011 (3)0.005 (3)
C790.038 (3)0.038 (4)0.029 (4)0.008 (3)0.004 (3)0.003 (3)
C800.031 (3)0.027 (3)0.030 (4)0.006 (2)0.009 (3)0.005 (3)
C810.038 (3)0.024 (3)0.032 (4)0.005 (2)0.003 (3)0.005 (3)
N710.037 (3)0.018 (3)0.027 (3)0.000 (2)0.002 (2)0.007 (2)
N900.087 (5)0.086 (5)0.060 (5)0.020 (4)0.014 (5)0.016 (4)
C900.097 (7)0.086 (6)0.067 (7)0.042 (5)0.010 (6)0.009 (5)
C910.095 (6)0.056 (5)0.062 (6)0.022 (4)0.002 (5)0.003 (4)
C920.103 (7)0.040 (4)0.068 (6)0.011 (4)0.038 (5)0.012 (4)
C930.091 (7)0.135 (9)0.054 (7)0.007 (6)0.011 (6)0.003 (5)
C940.109 (9)0.122 (9)0.075 (8)0.005 (7)0.007 (7)0.002 (6)
C950.082 (7)0.058 (5)0.095 (8)0.001 (5)0.004 (6)0.011 (5)
C960.072 (5)0.049 (5)0.072 (6)0.003 (4)0.015 (5)0.001 (4)
C970.064 (5)0.042 (4)0.052 (5)0.008 (3)0.013 (4)0.002 (3)
C980.083 (6)0.088 (6)0.062 (7)0.021 (5)0.011 (5)0.004 (5)
C990.088 (7)0.104 (7)0.057 (7)0.026 (5)0.004 (5)0.021 (5)
C1000.059 (5)0.064 (5)0.085 (7)0.015 (4)0.002 (5)0.012 (5)
C1010.078 (6)0.066 (5)0.055 (6)0.002 (4)0.016 (5)0.004 (4)
N910.066 (4)0.073 (4)0.060 (5)0.007 (3)0.015 (4)0.006 (3)
N1100.078 (5)0.080 (5)0.058 (5)0.008 (4)0.005 (4)0.011 (4)
C1100.092 (7)0.111 (8)0.074 (8)0.010 (6)0.017 (6)0.004 (6)
C1110.098 (7)0.097 (7)0.050 (6)0.013 (5)0.005 (5)0.017 (5)
C1120.043 (4)0.094 (6)0.041 (5)0.008 (4)0.011 (4)0.011 (5)
C1130.076 (6)0.083 (6)0.055 (6)0.009 (5)0.004 (5)0.004 (5)
C1140.080 (6)0.063 (5)0.076 (7)0.010 (4)0.013 (5)0.012 (5)
C1150.043 (4)0.094 (6)0.080 (7)0.006 (4)0.000 (5)0.011 (6)
C1160.063 (6)0.077 (6)0.088 (8)0.005 (5)0.011 (5)0.007 (6)
C1170.042 (4)0.100 (7)0.061 (6)0.009 (4)0.007 (4)0.032 (5)
C1180.053 (4)0.103 (7)0.047 (6)0.029 (4)0.002 (4)0.001 (4)
C1190.071 (6)0.084 (6)0.063 (7)0.027 (4)0.003 (5)0.006 (5)
C1200.083 (6)0.099 (8)0.055 (6)0.003 (5)0.016 (5)0.002 (5)
C1210.087 (6)0.089 (7)0.077 (8)0.015 (5)0.000 (5)0.006 (6)
N1110.078 (5)0.082 (5)0.059 (5)0.024 (4)0.007 (4)0.018 (4)
O10.119 (5)0.065 (3)0.059 (4)0.021 (3)0.018 (3)0.010 (3)
O20.096 (4)0.087 (4)0.057 (4)0.026 (3)0.008 (3)0.004 (3)
O30.078 (4)0.102 (5)0.060 (4)0.025 (3)0.012 (3)0.009 (3)
O40.085 (4)0.081 (4)0.058 (4)0.027 (3)0.005 (3)0.006 (3)
Geometric parameters (Å, º) top
Co1—N12.086 (5)C59—N511.341 (7)
Co1—N22.093 (4)C59—H590.9500
Co1—N31i2.145 (5)C60—N511.354 (7)
Co1—N302.163 (5)C60—C611.380 (8)
Co1—N102.165 (5)C60—H600.9500
Co1—N11ii2.185 (5)C61—H610.9500
Co2—N42.068 (4)N51—Co2vii2.159 (5)
Co2—N32.097 (4)N70—C741.320 (8)
Co2—N502.157 (5)N70—C701.348 (7)
Co2—N51iii2.159 (5)C70—C711.358 (8)
Co2—N71iv2.170 (4)C70—H700.9500
Co2—N702.175 (5)C71—C721.393 (8)
N1—C11.155 (6)C71—H710.9500
C1—S11.637 (6)C72—C731.384 (8)
N2—C21.158 (5)C72—C751.476 (9)
C2—S21.603 (5)C73—C741.404 (8)
N3—C31.163 (6)C73—H730.9500
C3—S31.605 (5)C74—H740.9500
N4—C41.152 (5)C75—C761.336 (8)
C4—S41.626 (5)C75—H750.9500
N10—C101.338 (7)C76—C771.468 (8)
N10—C141.353 (8)C76—H760.9500
C10—C111.368 (8)C77—C811.384 (8)
C10—H100.9500C77—C781.388 (8)
C11—C121.404 (9)C78—C791.401 (8)
C11—H110.9500C78—H780.9500
C12—C131.394 (8)C79—N711.327 (8)
C12—C151.450 (9)C79—H790.9500
C13—C141.357 (8)C80—N711.351 (7)
C13—H130.9500C80—C811.383 (8)
C14—H140.9500C80—H800.9500
C15—C161.322 (8)C81—H810.9500
C15—H150.9500N71—Co2viii2.170 (4)
C16—C171.477 (8)N90—C941.304 (12)
C16—H160.9500N90—C901.332 (12)
C17—C211.392 (8)C90—C911.405 (12)
C17—C181.404 (8)C90—H900.9500
C18—C191.400 (8)C91—C921.399 (11)
C18—H180.9500C91—H910.9500
C19—N111.324 (7)C92—C931.352 (12)
C19—H190.9500C92—C951.520 (13)
C20—N111.347 (7)C93—C941.385 (14)
C20—C211.362 (8)C93—H930.9500
C20—H200.9500C94—H940.9500
C21—H210.9500C95—C961.243 (11)
N11—Co1v2.185 (5)C95—H950.9500
N30—C341.334 (7)C96—C971.511 (11)
N30—C301.335 (7)C96—H960.9500
C30—C311.388 (8)C97—C981.370 (11)
C30—H300.9500C97—C1011.382 (10)
C31—C321.370 (8)C98—C991.396 (12)
C31—H310.9500C98—H980.9500
C32—C331.390 (8)C99—N911.324 (10)
C32—C351.472 (8)C99—H990.9500
C33—C341.391 (8)C100—N911.330 (10)
C33—H330.9500C100—C1011.382 (12)
C34—H340.9500C100—H1000.9500
C35—C361.330 (8)C101—H1010.9500
C35—H350.9500N110—C1101.323 (11)
C36—C371.471 (8)N110—C1141.356 (11)
C36—H360.9500C110—C1111.378 (13)
C37—C381.382 (8)C110—H1100.9500
C37—C411.387 (8)C111—C1121.361 (12)
C38—C391.388 (8)C111—H1110.9500
C38—H380.9500C112—C1131.381 (11)
C39—N311.336 (7)C112—C1151.495 (12)
C39—H390.9500C113—C1141.406 (12)
C40—N311.356 (7)C113—H1130.9500
C40—C411.372 (8)C114—H1140.9500
C40—H400.9500C115—C1161.260 (11)
C41—H410.9500C115—H1150.9500
N31—Co1vi2.145 (5)C116—C1171.505 (12)
N50—C501.348 (7)C116—H1160.9500
N50—C541.351 (7)C117—C1211.367 (12)
C50—C511.367 (8)C117—C1181.383 (10)
C50—H500.9500C118—C1191.437 (11)
C51—C521.391 (8)C118—H1180.9500
C51—H510.9500C119—N1111.323 (11)
C52—C531.372 (8)C119—H1190.9500
C52—C551.453 (8)C120—N1111.349 (11)
C53—C541.391 (8)C120—C1211.365 (13)
C53—H530.9500C120—H1200.9500
C54—H540.9500C121—H1210.9500
C55—C561.328 (7)O1—H1O10.8401
C55—H550.9500O1—H2O10.8402
C56—C571.475 (8)O2—H1O20.8401
C56—H560.9500O2—H2O20.8399
C57—C581.379 (8)O3—H1O30.8400
C57—C611.388 (8)O3—H2O30.8401
C58—C591.402 (8)O4—H1O40.8403
C58—H580.9500O4—H2O40.8403
N1—Co1—N2178.12 (15)C55—C56—C57125.4 (6)
N1—Co1—N31i89.22 (17)C55—C56—H56117.3
N2—Co1—N31i92.16 (19)C57—C56—H56117.3
N1—Co1—N3088.41 (18)C58—C57—C61117.5 (5)
N2—Co1—N3090.18 (19)C58—C57—C56123.0 (5)
N31i—Co1—N30177.31 (18)C61—C57—C56119.6 (5)
N1—Co1—N1090.58 (18)C57—C58—C59119.9 (5)
N2—Co1—N1090.75 (19)C57—C58—H58120.1
N31i—Co1—N1087.49 (16)C59—C58—H58120.1
N30—Co1—N1093.80 (18)N51—C59—C58122.3 (5)
N1—Co1—N11ii89.15 (18)N51—C59—H59118.8
N2—Co1—N11ii89.56 (19)C58—C59—H59118.8
N31i—Co1—N11ii90.45 (19)N51—C60—C61122.6 (5)
N30—Co1—N11ii88.24 (15)N51—C60—H60118.7
N10—Co1—N11ii177.9 (2)C61—C60—H60118.7
N4—Co2—N3179.1 (2)C60—C61—C57120.0 (6)
N4—Co2—N5091.03 (19)C60—C61—H61120.0
N3—Co2—N5089.90 (18)C57—C61—H61120.0
N4—Co2—N51iii89.52 (19)C59—N51—C60117.5 (5)
N3—Co2—N51iii89.54 (18)C59—N51—Co2vii119.8 (4)
N50—Co2—N51iii179.19 (18)C60—N51—Co2vii121.8 (4)
N4—Co2—N71iv90.96 (19)C74—N70—C70118.2 (5)
N3—Co2—N71iv88.98 (19)C74—N70—Co2121.5 (4)
N50—Co2—N71iv92.88 (19)C70—N70—Co2119.9 (4)
N51iii—Co2—N71iv87.70 (13)N70—C70—C71123.5 (5)
N4—Co2—N7091.86 (19)N70—C70—H70118.3
N3—Co2—N7088.19 (18)C71—C70—H70118.3
N50—Co2—N7088.26 (13)C70—C71—C72119.3 (5)
N51iii—Co2—N7091.14 (18)C70—C71—H71120.3
N71iv—Co2—N70176.94 (16)C72—C71—H71120.3
C1—N1—Co1169.4 (5)C73—C72—C71117.5 (5)
N1—C1—S1179.4 (5)C73—C72—C75119.9 (6)
C2—N2—Co1172.0 (5)C71—C72—C75122.5 (6)
N2—C2—S2179.3 (6)C72—C73—C74119.5 (6)
C3—N3—Co2174.2 (4)C72—C73—H73120.2
N3—C3—S3179.0 (7)C74—C73—H73120.2
C4—N4—Co2171.9 (4)N70—C74—C73121.9 (6)
N4—C4—S4178.5 (6)N70—C74—H74119.1
C10—N10—C14117.2 (5)C73—C74—H74119.1
C10—N10—Co1120.8 (4)C76—C75—C72124.3 (7)
C14—N10—Co1121.1 (4)C76—C75—H75117.8
N10—C10—C11123.1 (6)C72—C75—H75117.8
N10—C10—H10118.5C75—C76—C77124.0 (6)
C11—C10—H10118.5C75—C76—H76118.0
C10—C11—C12120.2 (5)C77—C76—H76118.0
C10—C11—H11119.9C81—C77—C78118.3 (5)
C12—C11—H11119.9C81—C77—C76121.4 (5)
C13—C12—C11115.9 (5)C78—C77—C76120.3 (6)
C13—C12—C15120.2 (6)C77—C78—C79118.9 (6)
C11—C12—C15123.9 (6)C77—C78—H78120.6
C14—C13—C12120.9 (6)C79—C78—H78120.6
C14—C13—H13119.6N71—C79—C78122.7 (5)
C12—C13—H13119.6N71—C79—H79118.7
N10—C14—C13122.8 (5)C78—C79—H79118.7
N10—C14—H14118.6N71—C80—C81122.4 (5)
C13—C14—H14118.6N71—C80—H80118.8
C16—C15—C12124.8 (6)C81—C80—H80118.8
C16—C15—H15117.6C80—C81—C77119.5 (5)
C12—C15—H15117.6C80—C81—H81120.2
C15—C16—C17123.9 (6)C77—C81—H81120.2
C15—C16—H16118.1C79—N71—C80118.2 (5)
C17—C16—H16118.1C79—N71—Co2viii123.2 (4)
C21—C17—C18116.4 (5)C80—N71—Co2viii118.2 (4)
C21—C17—C16123.5 (5)C94—N90—C90117.2 (9)
C18—C17—C16120.1 (5)N90—C90—C91121.9 (9)
C19—C18—C17120.1 (5)N90—C90—H90119.0
C19—C18—H18119.9C91—C90—H90119.0
C17—C18—H18119.9C92—C91—C90119.0 (9)
N11—C19—C18121.6 (5)C92—C91—H91120.5
N11—C19—H19119.2C90—C91—H91120.5
C18—C19—H19119.2C93—C92—C91117.7 (8)
N11—C20—C21123.3 (5)C93—C92—C95119.5 (8)
N11—C20—H20118.3C91—C92—C95122.7 (9)
C21—C20—H20118.3C92—C93—C94118.9 (10)
C20—C21—C17120.0 (5)C92—C93—H93120.5
C20—C21—H21120.0C94—C93—H93120.5
C17—C21—H21120.0N90—C94—C93125.1 (11)
C19—N11—C20118.5 (5)N90—C94—H94117.4
C19—N11—Co1v121.8 (4)C93—C94—H94117.4
C20—N11—Co1v118.8 (4)C96—C95—C92127.3 (10)
C34—N30—C30117.7 (5)C96—C95—H95116.3
C34—N30—Co1124.7 (4)C92—C95—H95116.3
C30—N30—Co1117.3 (4)C95—C96—C97124.9 (8)
N30—C30—C31123.0 (5)C95—C96—H96117.5
N30—C30—H30118.5C97—C96—H96117.5
C31—C30—H30118.5C98—C97—C101117.8 (8)
C32—C31—C30119.3 (5)C98—C97—C96117.2 (7)
C32—C31—H31120.3C101—C97—C96125.0 (7)
C30—C31—H31120.3C97—C98—C99118.2 (8)
C31—C32—C33118.3 (5)C97—C98—H98120.9
C31—C32—C35122.0 (5)C99—C98—H98120.9
C33—C32—C35119.7 (5)N91—C99—C98124.5 (8)
C32—C33—C34118.9 (5)N91—C99—H99117.8
C32—C33—H33120.6C98—C99—H99117.8
C34—C33—H33120.6N91—C100—C101122.7 (8)
N30—C34—C33122.8 (5)N91—C100—H100118.6
N30—C34—H34118.6C101—C100—H100118.6
C33—C34—H34118.6C100—C101—C97120.1 (8)
C36—C35—C32123.8 (6)C100—C101—H101120.0
C36—C35—H35118.1C97—C101—H101120.0
C32—C35—H35118.1C99—N91—C100116.7 (7)
C35—C36—C37125.8 (6)C110—N110—C114116.1 (8)
C35—C36—H36117.1N110—C110—C111124.8 (9)
C37—C36—H36117.1N110—C110—H110117.6
C38—C37—C41117.9 (5)C111—C110—H110117.6
C38—C37—C36119.6 (5)C112—C111—C110119.7 (9)
C41—C37—C36122.5 (5)C112—C111—H111120.2
C37—C38—C39119.6 (5)C110—C111—H111120.2
C37—C38—H38120.2C111—C112—C113117.7 (8)
C39—C38—H38120.2C111—C112—C115118.6 (8)
N31—C39—C38123.0 (5)C113—C112—C115123.7 (8)
N31—C39—H39118.5C112—C113—C114119.5 (8)
C38—C39—H39118.5C112—C113—H113120.2
N31—C40—C41123.8 (5)C114—C113—H113120.2
N31—C40—H40118.1N110—C114—C113122.1 (8)
C41—C40—H40118.1N110—C114—H114118.9
C40—C41—C37119.0 (5)C113—C114—H114118.9
C40—C41—H41120.5C116—C115—C112125.7 (9)
C37—C41—H41120.5C116—C115—H115117.2
C39—N31—C40116.6 (5)C112—C115—H115117.2
C39—N31—Co1vi121.4 (4)C115—C116—C117127.6 (10)
C40—N31—Co1vi121.7 (4)C115—C116—H116116.2
C50—N50—C54115.8 (5)C117—C116—H116116.2
C50—N50—Co2123.5 (4)C121—C117—C118117.1 (8)
C54—N50—Co2119.6 (4)C121—C117—C116120.5 (8)
N50—C50—C51124.1 (5)C118—C117—C116122.4 (9)
N50—C50—H50117.9C117—C118—C119118.7 (8)
C51—C50—H50117.9C117—C118—H118120.7
C50—C51—C52119.5 (6)C119—C118—H118120.7
C50—C51—H51120.3N111—C119—C118122.7 (8)
C52—C51—H51120.3N111—C119—H119118.6
C53—C52—C51117.7 (5)C118—C119—H119118.6
C53—C52—C55123.2 (6)N111—C120—C121123.3 (9)
C51—C52—C55119.1 (6)N111—C120—H120118.3
C52—C53—C54119.6 (5)C121—C120—H120118.3
C52—C53—H53120.2C120—C121—C117121.4 (9)
C54—C53—H53120.2C120—C121—H121119.3
N50—C54—C53123.2 (6)C117—C121—H121119.3
N50—C54—H54118.4C119—N111—C120116.8 (8)
C53—C54—H54118.4H1O1—O1—H2O1113.1
C56—C55—C52124.7 (6)H1O2—O2—H2O2101.6
C56—C55—H55117.6H1O3—O3—H2O3111.6
C52—C55—H55117.6H1O4—O4—H2O494.8
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x+3/2, y1/2, z1/2; (iv) x+3/2, y1/2, z+1/2; (v) x+1/2, y+1/2, z1/2; (vi) x1/2, y+1/2, z1/2; (vii) x+3/2, y+1/2, z+1/2; (viii) x+3/2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H2O1···O30.842.002.825 (8)169
O2—H2O2···O40.842.092.818 (8)144
O3—H2O3···N910.842.152.933 (9)156
O4—H1O4···N1100.842.142.885 (9)148
O1—H1O1···N90ix0.842.072.877 (10)160
O2—H1O2···N111x0.842.032.858 (10)170
O4—H2O4···O2xi0.842.102.844 (8)147
Symmetry codes: (ix) x+2, y+1, z1; (x) x, y, z+1; (xi) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H2O1···O30.842.002.825 (8)169
O2—H2O2···O40.842.092.818 (8)144
O3—H2O3···N910.842.152.933 (9)156
O4—H1O4···N1100.842.142.885 (9)148
O1—H1O1···N90i0.842.072.877 (10)160
O2—H1O2···N111ii0.842.032.858 (10)170
O4—H2O4···O2iii0.842.102.844 (8)147
Symmetry codes: (i) x+2, y+1, z1; (ii) x, y, z+1; (iii) x+1, y+1, z.
 

Acknowledgements

We gratefully acknowledge financial support by the DFG (project No. NA 720/5–1) and the State of Schleswig-Holstein. We thank Professor Dr Wolfgang Bensch for access to his experimental facility.

References

First citationBrandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationStoe (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.
First citationWöhlert, S., Boeckmann, J., Wriedt, M. & Näther, C. (2011). Angew. Chem. Int. Ed. 50, 6920–6923.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds