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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 9| September 2013| Pages m498-m499

cis-Di­aqua­tetra­kis­(1-butyl-1H-imidazole-κN3)nickel(II) dichloride

aDepartment of Physics, S. M. K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, bDepartment of Chemistry, Pondicherry University, Pondicherry 605 014, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
*Correspondence e-mail: a_sp59@yahoo.in

(Received 16 July 2013; accepted 10 August 2013; online 17 August 2013)

In the title compound, [Ni(C7H12N2)4(H2O)2]Cl2, the nickel(II) ion has a distorted octa­hedral coordination environment. It is surrounded by three N atoms and one O atom occupying the equatorial plane, and one N and one O atom in the axial positions. The imidazole ring systems are inclined to one another with dihedral angles varying between 38.3 (4) and 74.1 (4)°. In the crystal, mol­ecules are linked via O—H⋯Cl hydrogen bonds involving one Cl anion and the water mol­ecule in the equatorial plane, forming an inversion dimer-like arrangement. The water mol­ecule in the axial position is hydrogen-bonded to both Cl anions. There are also a number of C—H⋯Cl hydrogen bonds present, forming a three-dimensional structure. All four alkyl chains are disordered over two positions with refined occupancy ratios of 0.395 (15):0.605 (15), 0.658 (14):0.342 (14), 0.332 (11):0.668 (11) and 0.622 (12):0.378 (12).

Related literature

For biological and pharmaceutical properties of imidazoles and imidazole-containing compounds, see: Roman et al. (2007[Roman, G., Riley, J. G., Vlahakis, J. Z., Kinobe, R. T., Brien, J. F., Nakatsu, K. & Szarek, W. A. (2007). Bioorg. Med. Chem. 15, 3225-3234.]); Nanterment et al. (2004[Nanterment, P. G., Barrow, J. C., Lindsley, S. R., Young, M., Mao, S., Carroll, S., Bailey, C., Bosserman, M., Colussi, D., McMasters, D. R., Vacca, J. P. & Selnick, H. G. (2004). Bioorg. Med. Chem. Lett. 14, 2141-2145.]); Congiu et al. (2008[Congiu, C., Cocco, M. T. & Onnis, V. (2008). Bioorg. Med. Chem. Lett. 18, 989-993.]); Venkatesan et al. (2008[Venkatesan, A. M., Agarwal, A., Abe, T., Ushirogochi, H. O., Santos, D., Li, Z., Francisco, G., Lin, Y. I., Peterson, P. J., Yang, Y., Weiss, W. J., Shales, D. M. & Mansour, T. S. (2008). Bioorg. Med. Chem. 16, 1890-1902.]); Bhatnagar et al. (2011[Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. Pharm. Tech. Res. 3, 268-282.]); Puratchikody & Doble (2007[Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.]); Gaonkar et al. (2009[Gaonkar, S. L., Rai, K. M. L. & Shetty, N. S. (2009). Med. Chem. Res. 18, 221-230.]). For applications of imidazole and its derivatives in the construction of metal–organic frameworks, see: Huang et al. (2008[Huang, X.-F., Fu, D.-W. & Xiong, R.-G. (2008). Cryst. Growth Des. 8, 1795-1797.], 2011[Huang, Z.-J., Tang, J.-N., Luo, Z.-R., Wang, D.-Y. & Wei, H. (2011). Acta Cryst. E67, m408.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C7H12N2)4(H2O)2]Cl2

  • Mr = 662.39

  • Monoclinic, P 21 /n

  • a = 8.533 (5) Å

  • b = 24.952 (5) Å

  • c = 17.641 (5) Å

  • β = 101.277 (5)°

  • V = 3684 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.71 mm−1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Oxford Xcalibur diffractometer with Eos detector

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.790, Tmax = 0.816

  • 32409 measured reflections

  • 6451 independent reflections

  • 4027 reflections with I > 2σ(I)

  • Rint = 0.113

Refinement
  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.233

  • S = 1.04

  • 6451 reflections

  • 530 parameters

  • 707 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.69 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯Cl2i 0.84 (4) 2.35 (4) 3.165 (4) 164 (7)
O1—H1B⋯Cl1 0.84 (4) 2.37 (4) 3.185 (5) 166 (4)
O2—H2A⋯Cl2 0.86 (4) 2.43 (4) 3.250 (4) 160 (5)
O2—H2B⋯Cl2i 0.84 (6) 2.30 (5) 3.127 (4) 169 (5)
C3—H3⋯Cl2 0.93 2.67 3.593 (6) 171
C4—H4⋯Cl2 0.93 2.70 3.565 (8) 155
C5—H5⋯Cl1ii 0.93 2.72 3.640 (8) 173
C9—H9⋯Cl1 0.93 2.65 3.566 (7) 170
C10—H10⋯Cl1 0.93 2.67 3.562 (7) 160
C11—H11⋯Cl1iii 0.93 2.79 3.722 (7) 177
Symmetry codes: (i) -x, -y+1, -z; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Imidazoles have been reported to serve as useful building blocks for the synthesis of diverse classes of bioactive molecules. In addition, imidazole-containing compounds exhibit a wide spectrum of pharmaceutical properties such as pesticides, fungicides, antibacterial, anti-inflammatory, anti-tubercular, anti-diabetic, antimalarial and antitumour (Roman et al., 2007; Nanterment et al., 2004; Congiu et al., 2008; Venkatesan et al., 2008; Bhatnagar et al., 2011; Puratchikody & Doble 2007).

Knowledge of the detailed coordination behaviour of imidazoles and their limitation in the possible use in complexes with specific catalytic activity is of great current importance. Imidazoles, namely 1,3-diazacyclopenta-2,4-diene and its derivatives, have found a wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal–organic frameworks (Huang et al., 2008, 2011).

The chemistry of imidazole occupies an extremely important position within the family of five-membered heterocyclic compounds. Synthesis of imidazole derivatives has attracted great interest in recent years due to their broad spectrum of biological activities (Gaonkar et al., 2009). This paper describes the synthesis and crystal structure of the nickel(II) complex of the imidazole ligand 1-butyl-1H-imidazole.

The molecular structure of the title compound is illustrated in Fig. 1. The nickel(II) ion has a distorted octahedral coordination environment. It is surrounded by four N and two O atoms; an N and an O atom are in the axial positions, and the other three N atoms and an O atom are in the equatorial plane. The imidazole ring (N1/N2/C1–C3) makes dihedral angles of 44.7 (4)°, 38.3 (4)° and 74.1 (4)° with the other three imidazole rings (N3/N4/C4–C6), (N5/N6/C7–C9) and (N7/N8/C10–C12), respectively.

In the crystal, molecules are linked via O—H···Cl hydrogen bonds, involving one Cl- anion (Cl2) and the water molecule (O2) in the equatorial plane, to form an inversion dimer-like arrangement. The water molecule in the axial position (O1) is hydrogen-bonded to both Cl- anions. There are a number of C—H···Cl interactions present forming a three-dimensional structure. Details are given in Table 1.

Related literature top

For biological and pharmaceutical properties of imidazoles and imidazole-containing compounds, see: Roman et al. (2007); Nanterment et al. (2004); Congiu et al. (2008); Venkatesan et al. (2008); Bhatnagar et al. (2011); Puratchikody & Doble (2007); Gaonkar et al. (2009). For applications of imidazole and its derivatives in the construction of metal–organic frameworks, see: Huang et al. (2008, 2011).

Experimental top

NiCl2.6H2O (6.0 g) was dissolved in warm ethanol (3 ml). The solution was cooled in ice while adding slowly a solution of 1-butylimidazole (5.0 g in 5.6 ml EtOH); the reaction is quite exothermic. Cold ethanol (15 ml) was then added to initiate crystallization. The colourless crystalline solid was filtered and kept cold for 10 min then washed with two 5 ml portions of ethanol and dried in air.

Refinement top

Thy water H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93–0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl and = 1.2Ueq(C) for other H atoms. The four alkyl chains are disordered over two positions with refined occupancy ratios of 0.395 (15):0.605 (15); 0.658 (14):0.342 (14); 0.332 (11):0.668 (11); 0.622 (12):0.378 (12).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level. The H atoms have been omitted for clarity. The minor fraction of the disordered alkyl chains are indicated by dashed bonds and a suffix ' to the atom label.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the c axis. The O—H···Cl hydrogen bonds are shown as dashed lines [symmetry code (i): -x, -y+1, -z].
cis-Diaquatetrakis(1-butyl-1H-imidazole-κN3)nickel(II) dichloride top
Crystal data top
[Ni(C7H12N2)4(H2O)2]Cl2F(000) = 1416
Mr = 662.39Dx = 1.194 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6451 reflections
a = 8.533 (5) Åθ = 3.5–25.0°
b = 24.952 (5) ŵ = 0.71 mm1
c = 17.641 (5) ÅT = 293 K
β = 101.277 (5)°Block, colourless
V = 3684 (3) Å30.30 × 0.30 × 0.25 mm
Z = 4
Data collection top
Oxford Xcalibur
diffractometer with Eos detector
6451 independent reflections
Radiation source: fine-focus sealed tube4027 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.113
ω and ϕ scanθmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
h = 1010
Tmin = 0.790, Tmax = 0.816k = 2929
32409 measured reflectionsl = 2020
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)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.233H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.1168P)2 + 1.3167P]
where P = (Fo2 + 2Fc2)/3
6451 reflections(Δ/σ)max = 0.001
530 parametersΔρmax = 0.77 e Å3
707 restraintsΔρmin = 0.69 e Å3
Crystal data top
[Ni(C7H12N2)4(H2O)2]Cl2V = 3684 (3) Å3
Mr = 662.39Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.533 (5) ŵ = 0.71 mm1
b = 24.952 (5) ÅT = 293 K
c = 17.641 (5) Å0.30 × 0.30 × 0.25 mm
β = 101.277 (5)°
Data collection top
Oxford Xcalibur
diffractometer with Eos detector
6451 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
4027 reflections with I > 2σ(I)
Tmin = 0.790, Tmax = 0.816Rint = 0.113
32409 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.077707 restraints
wR(F2) = 0.233H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.77 e Å3
6451 reflectionsΔρmin = 0.69 e Å3
530 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 esds 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*/UeqOcc. (<1)
Ni10.11087 (7)0.36734 (2)0.08946 (4)0.0436 (2)
O10.2011 (5)0.35389 (15)0.0154 (2)0.0582 (12)
O20.0477 (4)0.42750 (14)0.0292 (2)0.0524 (11)
N10.2901 (5)0.42634 (17)0.1112 (3)0.0510 (14)
N20.4118 (6)0.50391 (18)0.1091 (3)0.0670 (19)
N30.0141 (5)0.37746 (17)0.1882 (3)0.0485 (12)
N40.1056 (9)0.4062 (2)0.2792 (4)0.103 (3)
N50.0736 (5)0.31456 (17)0.0473 (3)0.0502 (14)
N60.2252 (6)0.2556 (2)0.0259 (3)0.0745 (17)
N70.2726 (5)0.31154 (17)0.1466 (3)0.0510 (14)
N80.4466 (8)0.2478 (3)0.1766 (4)0.093 (2)
C10.4446 (6)0.4179 (3)0.1014 (4)0.067 (2)
C20.5172 (7)0.4648 (3)0.1000 (4)0.075 (2)
C30.2771 (6)0.4780 (2)0.1144 (4)0.0590 (19)
C40.0356 (9)0.4189 (3)0.2200 (4)0.075 (2)
C50.1008 (8)0.3523 (3)0.2850 (4)0.077 (2)
C60.0246 (7)0.3351 (2)0.2305 (3)0.064 (2)
C70.2319 (6)0.3209 (2)0.0543 (4)0.067 (2)
C80.3219 (7)0.2835 (3)0.0117 (4)0.077 (3)
C90.0765 (7)0.2748 (3)0.0015 (4)0.066 (2)
C100.3326 (8)0.2677 (2)0.1224 (4)0.069 (2)
C110.4640 (8)0.2782 (3)0.2388 (4)0.086 (3)
C120.3546 (7)0.3179 (3)0.2213 (4)0.071 (2)
C13'0.442 (3)0.5613 (5)0.1021 (11)0.087 (3)0.605 (15)
C14'0.453 (2)0.5875 (6)0.1800 (10)0.107 (3)0.605 (15)
C15'0.469 (3)0.6486 (6)0.1729 (10)0.121 (4)0.605 (15)
C16'0.534 (3)0.6707 (7)0.2533 (10)0.142 (5)0.605 (15)
C170.200 (2)0.4441 (7)0.3185 (11)0.135 (4)0.622 (12)
C180.3681 (19)0.4258 (7)0.3220 (13)0.147 (4)0.622 (12)
C190.439 (2)0.4703 (8)0.3679 (13)0.168 (4)0.622 (12)
C200.6165 (19)0.4634 (10)0.3481 (14)0.186 (6)0.622 (12)
C210.261 (3)0.2083 (5)0.0753 (9)0.101 (4)0.658 (14)
C220.284 (2)0.1570 (5)0.0313 (10)0.121 (4)0.658 (14)
C230.152 (3)0.1463 (7)0.0311 (13)0.165 (4)0.658 (14)
C240.159 (4)0.0888 (8)0.0465 (15)0.206 (7)0.658 (14)
C25'0.5629 (19)0.2053 (6)0.1663 (12)0.143 (4)0.668 (11)
C26'0.530 (2)0.1573 (7)0.2172 (12)0.173 (4)0.668 (11)
C27'0.370 (2)0.1356 (7)0.1799 (16)0.195 (5)0.668 (11)
C28'0.425 (3)0.0816 (7)0.1589 (16)0.224 (6)0.668 (11)
C24'0.001 (5)0.1041 (15)0.054 (2)0.186 (7)0.342 (14)
C250.522 (4)0.1950 (9)0.177 (2)0.143 (5)0.332 (11)
C260.453 (4)0.1712 (9)0.1018 (19)0.169 (5)0.332 (11)
C270.345 (4)0.1242 (14)0.106 (3)0.198 (5)0.332 (11)
C280.407 (6)0.0763 (11)0.067 (3)0.213 (7)0.332 (11)
C19'0.374 (3)0.4539 (16)0.2983 (16)0.161 (4)0.378 (12)
C130.421 (5)0.5635 (7)0.1108 (17)0.088 (4)0.395 (15)
C140.518 (3)0.5825 (8)0.1868 (15)0.093 (4)0.395 (15)
C150.549 (3)0.6419 (8)0.1878 (18)0.116 (4)0.395 (15)
C160.419 (4)0.6745 (9)0.211 (2)0.141 (6)0.395 (15)
C17'0.086 (3)0.4468 (10)0.3464 (13)0.127 (5)0.378 (12)
C18'0.246 (3)0.4415 (13)0.3706 (14)0.141 (4)0.378 (12)
C22'0.208 (4)0.1701 (10)0.0654 (16)0.109 (4)0.342 (14)
C20'0.532 (3)0.4663 (18)0.325 (2)0.175 (6)0.378 (12)
C21'0.289 (4)0.2223 (9)0.0909 (15)0.094 (4)0.342 (14)
C23'0.094 (4)0.1407 (13)0.006 (2)0.145 (5)0.342 (14)
Cl10.26436 (18)0.23800 (7)0.07888 (10)0.0737 (6)
Cl20.10336 (19)0.54034 (6)0.11212 (10)0.0692 (6)
H13D0.541700.566500.084100.1040*0.605 (15)
H14C0.544500.573500.216000.1280*0.605 (15)
H14D0.357600.579300.200100.1280*0.605 (15)
H15C0.542100.657000.138600.1460*0.605 (15)
H30.183500.495400.119800.0710*
H40.024100.453900.203700.0910*
H50.142400.331400.319900.0930*
H60.001000.299500.222300.0770*
H70.269700.347000.083900.0810*
H80.430600.277800.008700.0920*
H90.013600.261400.017400.0790*
H100.299200.252800.073600.0830*
H110.536300.273500.285100.1030*
H120.337700.345300.254600.0850*
H13C0.356700.577400.064800.1040*0.605 (15)
H20B0.644200.428200.363200.2790*0.622 (12)
H20C0.652700.467700.293400.2790*0.622 (12)
H21A0.174300.202800.102900.1220*0.658 (14)
H21B0.357300.215000.113400.1220*0.658 (14)
H22A0.380600.160100.010700.1450*0.658 (14)
H22B0.296500.127000.067000.1450*0.658 (14)
H23A0.161500.166900.076600.1980*0.658 (14)
H23B0.051100.155500.016400.1980*0.658 (14)
H24A0.073600.079200.088300.3090*0.658 (14)
H24B0.148400.069100.001000.3090*0.658 (14)
H24C0.259600.080500.060200.3090*0.658 (14)
H25C0.671600.218000.182800.1720*0.668 (11)
H25D0.547800.194600.112500.1720*0.668 (11)
H26C0.611600.130100.219400.2080*0.668 (11)
H26D0.528200.169300.269400.2080*0.668 (11)
H27C0.321600.156200.134800.2330*0.668 (11)
H27D0.297700.133300.215700.2330*0.668 (11)
H28D0.333500.060600.135800.3370*0.668 (11)
H28E0.480500.063900.204600.3370*0.668 (11)
H28F0.494600.085700.122800.3370*0.668 (11)
H15D0.366300.664500.151900.1460*0.605 (15)
H16D0.549500.708700.250200.2130*0.605 (15)
H16E0.634200.653800.274300.2130*0.605 (15)
H16F0.459100.663500.286200.2130*0.605 (15)
H17A0.206700.478200.291800.1620*0.622 (12)
H17B0.142100.449900.370800.1620*0.622 (12)
H18A0.365700.391600.348200.1770*0.622 (12)
H18B0.431800.422100.270300.1770*0.622 (12)
H19A0.400100.466000.423000.2020*0.622 (12)
H19B0.408500.505600.352700.2020*0.622 (12)
H20A0.666500.489800.375000.2790*0.622 (12)
H10.490600.384600.096600.0810*
H1A0.192 (9)0.3804 (14)0.045 (3)0.0870*
H1B0.208 (8)0.3255 (12)0.040 (3)0.0870*
H20.622000.469900.093800.0910*
H2A0.086 (7)0.4568 (14)0.043 (3)0.0780*
H2B0.005 (7)0.435 (2)0.005 (3)0.0780*
H13A0.314200.578300.103500.1060*0.395 (15)
H13B0.470100.575900.068800.1060*0.395 (15)
H14A0.461300.573600.227800.1120*0.395 (15)
H14B0.619200.563700.197000.1120*0.395 (15)
H15A0.648100.649200.223400.1400*0.395 (15)
H15B0.561500.653000.136700.1400*0.395 (15)
H16A0.445600.711800.210300.2120*0.395 (15)
H16B0.406900.664400.262000.2120*0.395 (15)
H16C0.320100.668100.175200.2120*0.395 (15)
H17C0.001000.437100.388100.1530*0.378 (12)
H17D0.069500.482900.329200.1530*0.378 (12)
H18C0.254000.466700.411700.1690*0.378 (12)
H18D0.260200.405500.388900.1690*0.378 (12)
H19C0.388400.423300.263600.1930*0.378 (12)
H19D0.342100.484400.270900.1930*0.378 (12)
H20D0.617500.468600.280900.2630*0.378 (12)
H20E0.522100.499800.352400.2630*0.378 (12)
H20F0.554300.438300.358700.2630*0.378 (12)
H21C0.259400.235400.138000.1130*0.342 (14)
H21D0.404100.219300.098500.1130*0.342 (14)
H22C0.300700.147100.069400.1310*0.342 (14)
H22D0.164800.161500.110900.1310*0.342 (14)
H23C0.070400.172100.026400.1740*0.342 (14)
H23D0.011000.141300.036700.1740*0.342 (14)
H24D0.094400.122000.079300.2790*0.342 (14)
H24E0.027900.072200.028900.2790*0.342 (14)
H24F0.064800.094600.090600.2790*0.342 (14)
H25A0.637200.198500.182400.1720*0.332 (11)
H25B0.499500.173100.218700.1720*0.332 (11)
H26A0.538500.159800.076800.2030*0.332 (11)
H26B0.392200.198500.069500.2030*0.332 (11)
H27A0.236600.132700.080500.2380*0.332 (11)
H27B0.343700.115900.160000.2380*0.332 (11)
H28A0.344000.045200.073300.3180*0.332 (11)
H28B0.516400.069800.091000.3180*0.332 (11)
H28C0.399300.083800.013400.3180*0.332 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0345 (4)0.0485 (4)0.0474 (4)0.0012 (3)0.0071 (3)0.0018 (3)
O10.063 (2)0.060 (2)0.055 (2)0.010 (2)0.020 (2)0.0009 (18)
O20.0412 (19)0.059 (2)0.058 (2)0.0088 (17)0.0125 (17)0.0086 (18)
N10.038 (2)0.052 (2)0.062 (3)0.0019 (18)0.007 (2)0.007 (2)
N20.051 (3)0.064 (3)0.085 (4)0.018 (2)0.011 (3)0.001 (3)
N30.045 (2)0.052 (2)0.050 (2)0.0002 (19)0.013 (2)0.0101 (19)
N40.161 (6)0.079 (4)0.092 (4)0.027 (4)0.080 (4)0.021 (3)
N50.034 (2)0.056 (2)0.059 (3)0.0009 (18)0.005 (2)0.004 (2)
N60.061 (3)0.094 (3)0.066 (3)0.027 (3)0.006 (3)0.025 (3)
N70.043 (2)0.058 (3)0.048 (2)0.0035 (19)0.001 (2)0.006 (2)
N80.086 (4)0.105 (4)0.089 (4)0.052 (4)0.018 (4)0.027 (3)
C10.039 (3)0.071 (3)0.095 (5)0.002 (3)0.020 (3)0.009 (3)
C20.043 (3)0.088 (4)0.099 (5)0.014 (3)0.023 (4)0.004 (4)
C30.045 (3)0.058 (3)0.074 (4)0.001 (2)0.012 (3)0.002 (3)
C40.106 (5)0.061 (3)0.070 (4)0.006 (4)0.044 (4)0.009 (3)
C50.076 (4)0.098 (4)0.066 (4)0.005 (4)0.033 (4)0.032 (3)
C60.072 (4)0.059 (3)0.062 (4)0.001 (3)0.017 (3)0.019 (3)
C70.033 (3)0.076 (4)0.092 (5)0.000 (3)0.009 (3)0.011 (3)
C80.036 (3)0.098 (5)0.094 (5)0.010 (3)0.003 (3)0.012 (4)
C90.050 (3)0.086 (4)0.064 (4)0.010 (3)0.018 (3)0.022 (3)
C100.075 (4)0.074 (4)0.059 (3)0.018 (3)0.013 (3)0.001 (3)
C110.050 (4)0.127 (6)0.073 (4)0.013 (4)0.006 (3)0.020 (4)
C120.065 (4)0.086 (4)0.055 (3)0.007 (3)0.002 (3)0.001 (3)
C13'0.084 (7)0.081 (5)0.098 (6)0.017 (5)0.021 (6)0.007 (5)
C14'0.116 (7)0.094 (5)0.109 (6)0.015 (6)0.015 (6)0.010 (5)
C15'0.129 (8)0.097 (6)0.135 (7)0.003 (7)0.018 (7)0.022 (6)
C16'0.147 (10)0.115 (8)0.154 (9)0.012 (8)0.007 (9)0.032 (7)
C170.149 (7)0.150 (7)0.124 (7)0.016 (6)0.075 (6)0.004 (6)
C180.138 (7)0.154 (8)0.150 (8)0.006 (6)0.028 (6)0.007 (6)
C190.151 (7)0.193 (8)0.169 (8)0.019 (7)0.052 (7)0.008 (7)
C200.153 (9)0.219 (12)0.193 (12)0.015 (10)0.053 (10)0.011 (11)
C210.099 (7)0.100 (6)0.100 (6)0.025 (6)0.008 (6)0.036 (5)
C220.130 (7)0.100 (5)0.133 (7)0.020 (6)0.024 (6)0.035 (5)
C230.170 (8)0.150 (7)0.171 (8)0.010 (7)0.025 (6)0.006 (7)
C240.215 (13)0.174 (9)0.220 (12)0.001 (10)0.019 (11)0.039 (10)
C25'0.140 (7)0.142 (7)0.153 (8)0.068 (5)0.044 (6)0.022 (6)
C26'0.184 (8)0.138 (6)0.194 (8)0.045 (6)0.030 (7)0.029 (6)
C27'0.194 (8)0.174 (8)0.213 (9)0.027 (6)0.033 (7)0.001 (7)
C28'0.241 (11)0.187 (9)0.234 (12)0.035 (9)0.021 (10)0.018 (9)
C24'0.187 (12)0.170 (11)0.190 (11)0.010 (10)0.012 (10)0.021 (10)
C250.147 (9)0.128 (7)0.156 (9)0.056 (6)0.033 (7)0.021 (6)
C260.169 (9)0.162 (8)0.177 (9)0.033 (7)0.034 (8)0.008 (7)
C270.201 (9)0.184 (9)0.206 (10)0.011 (7)0.032 (8)0.000 (7)
C280.226 (14)0.183 (10)0.220 (14)0.012 (11)0.023 (12)0.013 (11)
C19'0.154 (7)0.173 (8)0.158 (8)0.009 (7)0.037 (6)0.006 (7)
C130.091 (8)0.081 (5)0.094 (8)0.019 (5)0.020 (7)0.007 (6)
C140.089 (8)0.091 (6)0.098 (7)0.011 (6)0.016 (6)0.008 (6)
C150.119 (8)0.100 (6)0.126 (8)0.013 (6)0.014 (7)0.012 (6)
C160.151 (11)0.119 (9)0.150 (11)0.012 (9)0.021 (10)0.014 (9)
C17'0.140 (8)0.138 (8)0.112 (8)0.019 (8)0.047 (7)0.016 (7)
C18'0.144 (7)0.156 (8)0.134 (8)0.016 (7)0.053 (6)0.028 (7)
C22'0.117 (8)0.102 (7)0.108 (8)0.011 (7)0.023 (7)0.032 (6)
C20'0.151 (9)0.203 (11)0.176 (12)0.014 (11)0.043 (9)0.002 (11)
C21'0.091 (8)0.096 (7)0.092 (8)0.025 (6)0.008 (6)0.026 (6)
C23'0.152 (9)0.134 (8)0.145 (9)0.001 (7)0.020 (7)0.007 (7)
Cl10.0533 (9)0.0964 (12)0.0703 (10)0.0051 (8)0.0091 (8)0.0347 (9)
Cl20.0697 (10)0.0651 (9)0.0807 (11)0.0139 (7)0.0345 (9)0.0187 (8)
Geometric parameters (Å, º) top
Ni1—O12.164 (4)C12—H120.9300
Ni1—O22.157 (4)C13—H13B0.9700
Ni1—N12.103 (5)C13—H13A0.9700
Ni1—N32.084 (5)C13'—H13D0.9700
Ni1—N52.075 (5)C13'—H13C0.9700
Ni1—N72.077 (5)C14—H14A0.9700
O1—H1B0.84 (4)C14—H14B0.9700
O1—H1A0.84 (4)C14'—H14D0.9700
O2—H2A0.86 (4)C14'—H14C0.9700
O2—H2B0.84 (6)C15—H15B0.9700
N1—C11.379 (7)C15—H15A0.9700
N1—C31.296 (7)C15'—H15C0.9700
N2—C31.338 (7)C15'—H15D0.9700
N2—C13'1.465 (14)C16—H16B0.9600
N2—C131.489 (18)C16—H16C0.9600
N2—C21.358 (8)C16—H16A0.9600
N3—C41.287 (9)C16'—H16D0.9600
N3—C61.371 (7)C16'—H16E0.9600
N4—C171.497 (19)C16'—H16F0.9600
N4—C41.339 (10)C17—H17A0.9700
N4—C17'1.54 (2)C17—H17B0.9700
N4—C51.349 (9)C17'—H17C0.9700
N5—C71.389 (7)C17'—H17D0.9700
N5—C91.311 (9)C18—H18A0.9700
N6—C81.349 (8)C18—H18B0.9700
N6—C91.346 (8)C18'—H18C0.9700
N6—C211.463 (15)C18'—H18D0.9700
N6—C21'1.43 (3)C19—H19A0.9700
N7—C121.375 (9)C19—H19B0.9700
N7—C101.314 (7)C19'—H19C0.9700
N8—C101.320 (10)C19'—H19D0.9700
N8—C251.47 (3)C20—H20C0.9600
N8—C111.318 (10)C20—H20A0.9600
N8—C25'1.488 (18)C20—H20B0.9600
C1—C21.327 (10)C20'—H20D0.9600
C5—C61.333 (9)C20'—H20F0.9600
C7—C81.342 (9)C20'—H20E0.9600
C11—C121.355 (10)C21—H21B0.9700
C13—C141.51 (4)C21—H21A0.9700
C13'—C14'1.51 (2)C21'—H21C0.9700
C14—C151.51 (3)C21'—H21D0.9700
C14'—C15'1.54 (2)C22—H22A0.9700
C15—C161.50 (4)C22—H22B0.9700
C15'—C16'1.52 (2)C22'—H22C0.9700
C17—C181.52 (2)C22'—H22D0.9700
C17'—C18'1.51 (4)C23—H23A0.9700
C18—C191.56 (3)C23—H23B0.9700
C18'—C19'1.54 (4)C23'—H23C0.9700
C19—C201.50 (3)C23'—H23D0.9700
C19'—C20'1.54 (4)C24—H24A0.9600
C21—C221.53 (2)C24—H24B0.9600
C21'—C22'1.50 (4)C24—H24C0.9600
C22—C231.44 (3)C24'—H24D0.9600
C22'—C23'1.48 (4)C24'—H24E0.9700
C23—C241.46 (3)C24'—H24F0.9500
C23'—C24'1.50 (5)C25—H25A0.9700
C25—C261.47 (5)C25—H25B0.9700
C25'—C26'1.56 (3)C25'—H25D0.9700
C26—C271.50 (4)C25'—H25C0.9700
C26'—C27'1.50 (3)C26—H26B0.9700
C27—C281.53 (6)C26—H26A0.9700
C27'—C28'1.50 (3)C26'—H26C0.9700
C1—H10.9300C26'—H26D0.9700
C2—H20.9300C27—H27B0.9800
C3—H30.9300C27—H27A0.9700
C4—H40.9300C27'—H27D0.9700
C5—H50.9300C27'—H27C0.9700
C6—H60.9300C28—H28A0.9600
C7—H70.9300C28—H28C0.9500
C8—H80.9300C28—H28B0.9600
C9—H90.9300C28'—H28E0.9600
C10—H100.9300C28'—H28F0.9600
C11—H110.9300C28'—H28D0.9600
O1—Ni1—O288.88 (14)C16'—C15'—H15D110.00
O1—Ni1—N184.08 (17)H15C—C15'—H15D108.00
O1—Ni1—N3176.94 (16)C15—C16—H16B110.00
O1—Ni1—N588.11 (17)C15—C16—H16C109.00
O1—Ni1—N789.84 (17)H16A—C16—H16B110.00
O2—Ni1—N188.08 (16)H16A—C16—H16C109.00
O2—Ni1—N390.84 (16)H16B—C16—H16C109.00
O2—Ni1—N584.62 (16)C15—C16—H16A110.00
O2—Ni1—N7177.31 (16)H16E—C16'—H16F109.00
N1—Ni1—N398.95 (18)C15'—C16'—H16D110.00
N1—Ni1—N5169.4 (2)C15'—C16'—H16E110.00
N1—Ni1—N789.44 (17)C15'—C16'—H16F109.00
N3—Ni1—N588.84 (19)H16D—C16'—H16E109.00
N3—Ni1—N790.56 (19)H16D—C16'—H16F110.00
N5—Ni1—N797.70 (17)H17A—C17—H17B108.00
H1A—O1—H1B111 (5)N4—C17—H17A108.00
Ni1—O1—H1A114 (4)N4—C17—H17B108.00
Ni1—O1—H1B130 (4)C18—C17—H17A109.00
Ni1—O2—H2A134 (4)C18—C17—H17B108.00
Ni1—O2—H2B98 (4)C18'—C17'—H17C111.00
H2A—O2—H2B108 (5)C18'—C17'—H17D111.00
Ni1—N1—C1123.3 (4)N4—C17'—H17D112.00
Ni1—N1—C3129.7 (4)N4—C17'—H17C112.00
C1—N1—C3104.4 (5)H17C—C17'—H17D109.00
C2—N2—C13'124.1 (11)C17—C18—H18A111.00
C2—N2—C3105.0 (5)C17—C18—H18B111.00
C3—N2—C13121.6 (17)H18A—C18—H18B109.00
C2—N2—C13133.4 (17)C19—C18—H18B111.00
C3—N2—C13'130.3 (11)C19—C18—H18A111.00
C4—N3—C6104.3 (5)C19'—C18'—H18C110.00
Ni1—N3—C6122.6 (3)C17'—C18'—H18D111.00
Ni1—N3—C4132.8 (4)C17'—C18'—H18C111.00
C4—N4—C17'116.5 (11)C19'—C18'—H18D110.00
C5—N4—C17127.3 (9)H18C—C18'—H18D109.00
C4—N4—C17125.1 (8)H19A—C19—H19B109.00
C4—N4—C5106.5 (6)C18—C19—H19A110.00
C5—N4—C17'126.8 (10)C18—C19—H19B110.00
Ni1—N5—C9129.2 (4)C20—C19—H19A111.00
Ni1—N5—C7125.3 (4)C20—C19—H19B111.00
C7—N5—C9104.5 (5)C18'—C19'—H19C110.00
C8—N6—C21'121.3 (14)C20'—C19'—H19D110.00
C8—N6—C9106.8 (5)C18'—C19'—H19D110.00
C8—N6—C21129.2 (11)C20'—C19'—H19C110.00
C9—N6—C21'130.4 (15)H19C—C19'—H19D108.00
C9—N6—C21123.5 (11)C19—C20—H20A109.00
Ni1—N7—C10131.6 (5)H20B—C20—H20C109.00
C10—N7—C12104.5 (5)C19—C20—H20B109.00
Ni1—N7—C12123.6 (4)C19—C20—H20C110.00
C10—N8—C25127.0 (15)H20A—C20—H20B109.00
C10—N8—C25'126.5 (10)H20A—C20—H20C109.00
C10—N8—C11109.5 (7)C19'—C20'—H20F109.00
C11—N8—C25'122.9 (10)H20D—C20'—H20E110.00
C11—N8—C25122.4 (15)C19'—C20'—H20E109.00
N1—C1—C2109.2 (6)C19'—C20'—H20D110.00
N2—C2—C1108.0 (5)H20E—C20'—H20F109.00
N1—C3—N2113.3 (5)H20D—C20'—H20F110.00
N3—C4—N4112.7 (6)N6—C21—H21B109.00
N4—C5—C6106.2 (6)N6—C21—H21A109.00
N3—C6—C5110.4 (5)H21A—C21—H21B108.00
N5—C7—C8109.3 (5)C22—C21—H21A109.00
N6—C8—C7107.2 (5)C22—C21—H21B109.00
N5—C9—N6112.0 (5)N6—C21'—H21D112.00
N7—C10—N8110.9 (6)H21C—C21'—H21D110.00
N8—C11—C12105.7 (6)C22'—C21'—H21C112.00
N7—C12—C11109.4 (6)C22'—C21'—H21D112.00
N2—C13—C14110.5 (19)N6—C21'—H21C112.00
N2—C13'—C14'109.1 (13)C21—C22—H22A109.00
C13—C14—C15113 (2)C21—C22—H22B109.00
C13'—C14'—C15'110.3 (13)C23—C22—H22A109.00
C14—C15—C16114 (2)C23—C22—H22B109.00
C14'—C15'—C16'107.8 (14)H22A—C22—H22B108.00
N4—C17—C18115.3 (14)C21'—C22'—H22C100.00
N4—C17'—C18'101.0 (18)C21'—C22'—H22D100.00
C17—C18—C19105.8 (14)C23'—C22'—H22C100.00
C17'—C18'—C19'106 (2)C23'—C22'—H22D100.00
C18—C19—C20105.9 (17)H22C—C22'—H22D104.00
C18'—C19'—C20'108 (2)H23A—C23—H23B108.00
N6—C21—C22113.9 (12)C22—C23—H23A111.00
N6—C21'—C22'101 (2)C22—C23—H23B111.00
C21—C22—C23112.6 (15)C24—C23—H23A111.00
C21'—C22'—C23'148 (3)C24—C23—H23B111.00
C22—C23—C24105.7 (19)C24'—C23'—H23C93.00
C22'—C23'—C24'170 (3)C24'—C23'—H23D93.00
N8—C25—C26105 (2)C22'—C23'—H23D93.00
N8—C25'—C26'106.2 (13)C22'—C23'—H23C93.00
C25—C26—C27114 (3)H23C—C23'—H23D103.00
C25'—C26'—C27'106.1 (16)C23—C24—H24A110.00
C26—C27—C28109 (3)C23—C24—H24B109.00
C26'—C27'—C28'97.5 (16)H24A—C24—H24C110.00
N1—C1—H1125.00H24B—C24—H24C110.00
C2—C1—H1125.00C23—C24—H24C109.00
N2—C2—H2126.00H24A—C24—H24B109.00
C1—C2—H2126.00C23'—C24'—H24F110.00
N1—C3—H3123.00H24E—C24'—H24F110.00
N2—C3—H3123.00H24D—C24'—H24E109.00
N3—C4—H4124.00H24D—C24'—H24F110.00
N4—C4—H4124.00C23'—C24'—H24D109.00
N4—C5—H5127.00C23'—C24'—H24E109.00
C6—C5—H5127.00N8—C25—H25B111.00
N3—C6—H6125.00C26—C25—H25A110.00
C5—C6—H6125.00C26—C25—H25B111.00
N5—C7—H7125.00H25A—C25—H25B109.00
C8—C7—H7125.00N8—C25—H25A111.00
N6—C8—H8126.00H25C—C25'—H25D109.00
C7—C8—H8126.00N8—C25'—H25D111.00
N5—C9—H9124.00N8—C25'—H25C111.00
N6—C9—H9124.00C26'—C25'—H25C110.00
N7—C10—H10124.00C26'—C25'—H25D110.00
N8—C10—H10125.00C25—C26—H26B109.00
N8—C11—H11127.00C25—C26—H26A109.00
C12—C11—H11127.00H26A—C26—H26B108.00
N7—C12—H12125.00C27—C26—H26A109.00
C11—C12—H12125.00C27—C26—H26B108.00
N2—C13—H13B109.00C25'—C26'—H26C111.00
C14—C13—H13A110.00C27'—C26'—H26D110.00
C14—C13—H13B110.00H26C—C26'—H26D109.00
H13A—C13—H13B108.00C25'—C26'—H26D110.00
N2—C13—H13A109.00C27'—C26'—H26C111.00
H13C—C13'—H13D108.00H27A—C27—H27B108.00
N2—C13'—H13D110.00C28—C27—H27A110.00
N2—C13'—H13C110.00C28—C27—H27B110.00
C14'—C13'—H13C110.00C26—C27—H27A110.00
C14'—C13'—H13D110.00C26—C27—H27B110.00
C13—C14—H14B109.00C26'—C27'—H27C112.00
C13—C14—H14A109.00C26'—C27'—H27D112.00
H14A—C14—H14B108.00C28'—C27'—H27C112.00
C15—C14—H14A109.00C28'—C27'—H27D112.00
C15—C14—H14B109.00H27C—C27'—H27D110.00
C13'—C14'—H14C110.00C27—C28—H28B109.00
C15'—C14'—H14D109.00C27—C28—H28C109.00
H14C—C14'—H14D108.00H28A—C28—H28B109.00
C13'—C14'—H14D110.00H28A—C28—H28C110.00
C15'—C14'—H14C110.00H28B—C28—H28C110.00
H15A—C15—H15B108.00C27—C28—H28A109.00
C16—C15—H15A109.00H28E—C28'—H28F110.00
C16—C15—H15B109.00C27'—C28'—H28D109.00
C14—C15—H15A109.00C27'—C28'—H28E109.00
C14—C15—H15B109.00C27'—C28'—H28F109.00
C14'—C15'—H15C110.00H28D—C28'—H28E109.00
C14'—C15'—H15D110.00H28D—C28'—H28F110.00
C16'—C15'—H15C110.00
O1—Ni1—N1—C145.5 (5)C6—N3—C4—N40.9 (8)
O2—Ni1—N1—C1134.6 (5)C4—N3—C6—C51.9 (7)
N3—Ni1—N1—C1134.9 (5)Ni1—N3—C4—N4173.1 (5)
N7—Ni1—N1—C144.4 (5)Ni1—N3—C6—C5172.8 (4)
O1—Ni1—N1—C3113.5 (6)C5—N4—C4—N30.5 (9)
O2—Ni1—N1—C324.4 (6)C17—N4—C4—N3168.7 (10)
N3—Ni1—N1—C366.1 (6)C4—N4—C5—C61.6 (8)
N7—Ni1—N1—C3156.6 (6)C4—N4—C17—C18125.2 (14)
O2—Ni1—N3—C437.4 (6)C5—N4—C17—C1841 (2)
N1—Ni1—N3—C450.8 (6)C17—N4—C5—C6169.5 (11)
N5—Ni1—N3—C4122.0 (6)C7—N5—C9—N60.1 (7)
N7—Ni1—N3—C4140.3 (6)Ni1—N5—C9—N6168.8 (4)
O2—Ni1—N3—C6135.6 (4)Ni1—N5—C7—C8171.7 (4)
N1—Ni1—N3—C6136.2 (4)C9—N5—C7—C82.2 (7)
N5—Ni1—N3—C651.0 (4)C21—N6—C8—C7175.2 (9)
N7—Ni1—N3—C646.7 (4)C9—N6—C21—C2299.0 (18)
O1—Ni1—N5—C7140.3 (5)C21—N6—C9—N5174.5 (8)
O2—Ni1—N5—C751.3 (5)C8—N6—C9—N52.3 (8)
N3—Ni1—N5—C739.7 (5)C8—N6—C21—C2271.4 (19)
N7—Ni1—N5—C7130.1 (5)C9—N6—C8—C73.6 (8)
O1—Ni1—N5—C926.5 (6)C12—N7—C10—N81.1 (7)
O2—Ni1—N5—C9115.5 (6)Ni1—N7—C10—N8172.4 (5)
N3—Ni1—N5—C9153.5 (6)Ni1—N7—C12—C11172.8 (4)
N7—Ni1—N5—C963.1 (6)C10—N7—C12—C111.4 (7)
O1—Ni1—N7—C1032.4 (5)C10—N8—C11—C120.5 (8)
N1—Ni1—N7—C10116.4 (5)C11—N8—C25'—C26'76.8 (14)
N3—Ni1—N7—C10144.6 (5)C25'—N8—C11—C12168.7 (10)
N5—Ni1—N7—C1055.7 (6)C25'—N8—C10—N7167.3 (9)
O1—Ni1—N7—C12140.1 (5)C11—N8—C10—N70.4 (9)
N1—Ni1—N7—C1256.0 (5)C10—N8—C25'—C26'117.1 (14)
N3—Ni1—N7—C1242.9 (5)N1—C1—C2—N20.2 (8)
N5—Ni1—N7—C12131.8 (5)N4—C5—C6—N32.2 (8)
Ni1—N1—C1—C2164.1 (5)N5—C7—C8—N63.7 (8)
C3—N1—C1—C20.6 (8)N8—C11—C12—N71.2 (8)
Ni1—N1—C3—N2163.3 (4)N2—C13'—C14'—C15'174.7 (16)
C1—N1—C3—N21.3 (8)C13'—C14'—C15'—C16'161.5 (19)
C13'—N2—C2—C1172.9 (10)N4—C17—C18—C19177.8 (14)
C13'—N2—C3—N1172.7 (11)C17—C18—C19—C20160.4 (17)
C3—N2—C2—C11.0 (7)N6—C21—C22—C2353 (2)
C2—N2—C3—N11.5 (8)C21—C22—C23—C24158.1 (19)
C2—N2—C13'—C14'113.4 (15)N8—C25'—C26'—C27'68.5 (17)
C3—N2—C13'—C14'76.8 (19)C25'—C26'—C27'—C28'115.7 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···Cl2i0.84 (4)2.35 (4)3.165 (4)164 (7)
O1—H1B···Cl10.84 (4)2.37 (4)3.185 (5)166 (4)
O2—H2A···Cl20.86 (4)2.43 (4)3.250 (4)160 (5)
O2—H2B···Cl2i0.84 (6)2.30 (5)3.127 (4)169 (5)
C3—H3···Cl20.932.673.593 (6)171
C4—H4···Cl20.932.703.565 (8)155
C5—H5···Cl1ii0.932.723.640 (8)173
C9—H9···Cl10.932.653.566 (7)170
C10—H10···Cl10.932.673.562 (7)160
C11—H11···Cl1iii0.932.793.722 (7)177
Symmetry codes: (i) x, y+1, z; (ii) x1/2, y+1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···Cl2i0.84 (4)2.35 (4)3.165 (4)164 (7)
O1—H1B···Cl10.84 (4)2.37 (4)3.185 (5)166 (4)
O2—H2A···Cl20.86 (4)2.43 (4)3.250 (4)160 (5)
O2—H2B···Cl2i0.84 (6)2.30 (5)3.127 (4)169 (5)
C3—H3···Cl20.932.673.593 (6)171
C4—H4···Cl20.932.703.565 (8)155
C5—H5···Cl1ii0.932.723.640 (8)173
C9—H9···Cl10.932.653.566 (7)170
C10—H10···Cl10.932.673.562 (7)160
C11—H11···Cl1iii0.932.793.722 (7)177
Symmetry codes: (i) x, y+1, z; (ii) x1/2, y+1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

ASP and PSK thank the Department of Chemistry, Pondicherry University, for the single-crystal XRD instrumentation facility. KA thanks CSIR, New Delhi [Lr: No. 01 (2570)/12/EMR-II/3.4.2012], for financial support through a Major Research Project.

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Volume 69| Part 9| September 2013| Pages m498-m499
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