research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages 779-782
doi:10.1107/S205698901501110X

Crystal structure of trans-(1,8-di­butyl-1,3,6,8,10,13-hexa­aza­cyclo­tetra­decane-κ4N3,N6,N10,N13)bis­­(thio­cyanato-κN)nickel(II) from synchrotron data

CROSSMARK_Color_square_no_text.svg
Dae-Woong Kim,a Jong Jin Kim,b Jong Won Shin,c Jin Hong Kimc and Dohyun Moonc*

aDepartment of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu, 702-701, Republic of Korea, bDepartment of Applied Chemistry, College of Engineering, Kyungpook National University, Daegu, 702-701, Republic of Korea, and cBeamline Department, Pohang Accelerator Laboratory 80, Jigokro-127-beongil, Nam-Gu Pohang, Gyeongbuk 790-784, South Korea
*Correspondence e-mail: dmoon@postech.ac.kr

Edited by M. Gdaniec, Adam Mickiewicz University, Poland (Received 28 May 2015; accepted 8 June 2015; online 13 June 2015)

The crystal structure of the title compound, [Ni(NCS)2(C16H38N6)], has been determined from synchrotron data. The asymmetric unit consists of two halves of the complex mol­ecules which have their NiII atoms located on inversion centres. The NiII ions show a tetra­gonally distorted octa­hedral coordination geometry, with four secondary amine N atoms of the aza­macrocyclic ligand in the equatorial plane and two N atoms of the thio­cyanate anions in the axial positions. The average equatorial Ni—N bond length [2.070 (5) Å] is shorter than the average axial Ni—N bond length [2.107 (18) Å]. Only half of the macrocyclic ligand N—H groups are involved in hydrogen bonding. The complex mol­ecules are connected via inter­molecular N—H⋯S hydrogen bonds into two symmetry-independent one-dimensional polymeric structures extending along the b-axis direction. One of the n-butyl substituents of the macrocycle exhibits conformational disorder with a refined occupancy ratio of 0.630:0.370.

CCDC reference: 1405450

1. Chemical context

Coordination compounds, including those formed by macrocyclic ligands, have attracted wide inter­est of material sciences, because of their potential applications (Lehn, 1995[Lehn, J.-M. (1995). In Supramolecular Chemistry; Concepts and Perspectives. Weinheim: VCH.]; Zhou et al., 2012[Zhou, Z., Shen, M., Cao, C., Liu, Q. & Yan, Z. (2012). Chem. Eur. J. 18, 7675-7679.]). In particular, NiII macrocyclic complexes having vacant sites in the axial positions have been used for the synthesis of new supra­molecular materials with inter­esting properties, including chiral recognition (Ryoo et al., 2010[Ryoo, J. J., Shin, J. W., Dho, H. S. & Min, K. S. (2010). Inorg. Chem. 49, 7232-7234.]) and gas storage (Suh et al., 2012[Suh, M. P., Park, H. J., Prasad, T. K. & Lim, D.-W. (2012). Chem. Rev. 112, 782-835.]). For example, NiII complexes with alkyl-substituted tetra-aza­macrocyclic ligands and anionic tetra­zole derivatives, metal cyanide and azide (Shen et al., 2012[Shen, X., Zhou, H., Zhang, Q., Xu, Y. & Zhou, H. (2012). Eur. J. Inorg. Chem. pp. 5050-5057.]; Kim et al., 2015[Kim, D.-W., Shin, J. W., Kim, J. H. & Moon, D. (2015). Acta Cryst. E71, 173-175.]) have been studied as magnetic materials and substrates for crystal engineering. The thio­cyanate ion is a versatile anionic ligand which can easily bind to a transition metal ion as a terminal or bridging ligand through the nitro­gen and/or the sulfur atoms, thus allowing the assembly of multi-dimensional compounds or heterometallic complexes (Safarifard & Morsali, 2012[Safarifard, V. & Morsali, A. (2012). CrystEngComm, 14, 5130-5132.]; Wang & Wang, 2015[Wang, H.-T. & Wang, X.-L. (2015). Acta Cryst. C71, 318-321.]). Here, we report the synthesis and crystal structure of an NiII complex with an aza­macrocycle ligand and two thio­cyanate anions, trans-(1,8-dibutyl-1,3,6,8,10,13-hexa­aza­cyclo­tetra­decane-κ4N3,N6,N10,N13)bis(thio­cyanato-κN)nickel(II) (I)[link].

[Scheme 1]

2. Structural commentary

The title compound (I)[link] contains two crystallographically independent complex mol­ecules that are centrosymmetric. Each NiII ion lies on an inversion centre and is coordinated by four secondary amine N atoms of the aza­macrocyclic ligand in a square-planar fashion in the equatorial plane, and by two N atoms from the thio­cyanate anions at the axial positions, resulting in a tetra­gonally distorted octa­hedral geometry, as shown in Fig. 1[link]. The average equatorial bond lengths, Ni1A—Neq and Ni1B—Neq, are 2.070 (8) and 2.070 (3) Å, respectively. The axial bond lengths, Ni1A—Nax and Ni1B—Nax are 2.119 (1) and 2.093 (1) Å, respectively. The axial bonds are longer than the equatorial bonds, which can be attributed either to a large Jahn–Teller distortion effect of the NiII ion and/or to a ring contraction of the aza­macrocyclic ligand (Halcrow, 2013[Halcrow, M. A. (2013). Chem. Soc. Rev. 42, 1784-1795.]; Kim et al., 2015[Kim, D.-W., Shin, J. W., Kim, J. H. & Moon, D. (2015). Acta Cryst. E71, 173-175.]). The average N—C and C—S bond lengths of the thiocyanate ligands are 1.157 (1) and 1.627 (11) Å, respectively. The former is very similar to a C≡N triple-bond length, while the latter is slightly shorter than reported C—S single-bond lengths (Bradforth et al., 1993[Bradforth, S. E., Kim, E. H., Arnold, D. W. & Neumark, D. M. (1993). J. Chem. Phys. 98, 800-810.]; Shin et al., 2010[Shin, J. W., Rowthu, S. R., Ryoo, J. J. & Min, K. S. (2010). Acta Cryst. E66, m919-m920.]). The six-membered chelate rings involving C2A, C3A and C2B, C3B atoms adopt a chair conformation, whereas the five-membered chelate rings involving C1A, C4A and C1B, C4B assume a gauche conformation (Min & Suh, 2001[Min, K. S. & Suh, M. P. (2001). Chem. Eur. J. 7, 303-313.]; Kim et al., 2015[Kim, D.-W., Shin, J. W., Kim, J. H. & Moon, D. (2015). Acta Cryst. E71, 173-175.]).

[Figure 1]
Figure 1
View of the mol­ecular structure of the title compound, showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. The minor position of the n-butyl substituent in the A mol­ecule is not shown.

3. Supra­molecular features

The S atoms of the thio­cyanate groups form inter­molecular N—H⋯S hydrogen bonds with adjacent secondary amine groups of the aza­macrocyclic ligand, giving rise to two symmetry-independent one-dimensional polymeric chains propagating along the b-axis direction (Fig. 2[link] and Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1A⋯S1Ai 1.00 2.73 3.5154 (17) 136
N2B—H2B⋯S1Bii 1.00 2.66 3.4556 (17) 137
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z.
[Figure 2]
Figure 2
View of the crystal packing, with N—H⋯S hydrogen bonds drawn as red dashed lines. H atoms have been omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (Version 5.36, Feb 2015 with two updates; Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) indicated one complex of NiII with the same aza­maclocyclic ligand having an anionic tetra­zole derivative at the axial positions (Kim et al., 2015[Kim, D.-W., Shin, J. W., Kim, J. H. & Moon, D. (2015). Acta Cryst. E71, 173-175.]).

5. Synthesis and crystallization

The title compound (I)[link] was prepared as follows. The starting complex, [Ni(C16H38N6)](ClO4)2, was prepared by a slightly modified method reported by Jung et al. (1989[Jung, S. K., Kang, S. G. & Suh, M. P. (1989). Bull. Korean Chem. Soc. 10, 362-366.]). To a MeCN solution (10 mL) of [Ni(C16H38N6)](ClO4)2 (0.15 g, 0.26 mmol) was slowly added a MeCN solution (5 mL) containing sodium thio­cyanate (0.042 g, 0.52 mmol) at room temperature. A pale-pink precipitate was formed, which was filtered off, washed with MeCN, and diethyl ether, and dried in air. Single crystals of the title compound were obtained by layering of the MeCN solution of sodium thio­cyanate on the MeCN solution of [Ni(C16H38N6)](ClO4)2 for several days. Yield: 0.062 g (49%). FT–IR (KBr, cm−1): 3304, 3243, 2929, 2867, 2069, 1468, 1386, 1273, 1204, 1070, 925.

Safety note: Although we have experienced no problem with the compounds reported in this study, perchlorate salts of metal complexes are often explosive and should be handled with great caution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.98–0.99 Å and an N–H distance of 1.0 Å with Uiso(H) values of 1.2 or 1.5Ueq of the parent atoms. The C7A and C8A atoms of the macrocyclic ligand were refined as disordered over two sets of sites (C71A, C72A and C81A, C82A) with refined occupancies of 0.630 and 0.370, respectively. The bond lengths and angles of the disordered part were restrained to ensure proper geometry using DFIX and DANG instructions of SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]).

Table 2
Experimental details

Crystal data
Chemical formula [Ni(NCS)2(C16H38N6)]
Mr 489.39
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 180
a, b, c (Å) 8.6610 (17), 12.027 (2), 12.560 (3)
α, β, γ (°) 94.66 (3), 97.99 (3), 110.04 (3)
V (Å3) 1205.4 (5)
Z 2
Radiation type Synchrotron, λ = 0.630 Å
μ (mm−1) 0.72
Crystal size (mm) 0.25 × 0.15 × 0.13
 
Data collection
Diffractometer ADSC Q210 CCD area detector
Absorption correction Empirical (using intensity measurements) (HKL3000sm SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. Academic Press, New York.])
Tmin, Tmax 0.841, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections 12812, 6583, 6243
Rint 0.014
(sin θ/λ)max (Å−1) 0.696
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.111, 1.06
No. of reflections 6583
No. of parameters 287
No. of restraints 11
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.58, −1.11
Computer programs: PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983[Arvai, A. J. & Nielsen, C. (1983). ADSC Quantum-210 ADX. Area Detector System Corporation, Poway, CA, USA.]), HKL3000sm (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. Academic Press, New York.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Putz & Brandenburg, 2007[Putz, H. & Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1405450

Crystal structure: contains datablock I. DOI: 10.1107/S205698901501110X/gk2635sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901501110X/gk2635Isup2.hkl

checkCIF report


Chemical context top

Coordination compounds, including those formed by macrocyclic ligands, have attracted wide inter­est of material sciences, because of their potential applications (Lehn, 1995; Zhou et al., 2012). In particular, NiII macrocyclic complexes having vacant sites in the axial positions have been used for the synthesis of new supra­molecular materials with inter­esting properties, including chiral recognition (Ryoo et al., 2010) and gas storage (Suh et al., 2012). For example, NiII complexes with alkyl-substituted tetra-aza­macrocyclic ligands and anionic tetra­zole derivatives, metal cyanide and azide (Shen et al., 2012; Kim et al., 2015) have been studied as magnetic materials and substrates for crystal engineering. The thio­cyanate ion is a versatile anionic ligand which can easily bind to a transition metal ion as a terminal or bridging ligand through the nitro­gen and/or the sulfur atoms, thus allowing the assembly of multi-dimensional compounds or heterometallic complexes (Safarifard & Morsali, 2012; Wang & Wang 2015). Here, we report the synthesis and crystal structure of an NiII complex with aza­macrocycle and two thio­cyanate anions, trans-(1,8-di­butyl-1,3,6,8,10,13-hexa­aza­cyclo­tetra­decane-κ4N3,N6,N10,N13)bis­(thio­cyanato-κN)nickel(II) (I).

Structural commentary top

The title compound (I) contains two crystallographically independent complex molecules that are centrosymmetric. Each NiII ion lies on an inversion centre and is coordinated by four secondary amine N atoms of the aza­macrocyclic ligand in a square-planar fashion in the equatorial plane, and by two N atoms from the thio­cyanate anions at the axial positions, resulting in a tetra­gonally distorted o­cta­hedral geometry, as shown in Fig. 1. The average equatorial bond lengths, Ni1A—Neq and Ni1B—Neq, are 2.070 (1) and 2.070 (1) Å, respectively. The axial bond lengths, Ni1A—Nax and Ni1B—Nax are 2.119 (1) and 2.093 (1) Å, respectively. The axial bonds are longer than the equatorial bonds, which can be attributed either to a large Jahn–Teller distortion effect of the NiII ion and/or to a ring contraction of the aza­macrocyclic ligand (Halcrow, 2013; Kim et al., 2015). The average N—C and C—S bond lengths of the coordinated thio­cyanate ions are 1.157 (1) and 1.627 (1) Å, respectively. The former is very similar to a C≡N triple-bond distance, while the latter is slightly shorter than reported C—S single-bond distances (Bradforth et al., 1993; Shin et al., 2010). The six-membered chelate rings involving C2A, C3A and C2B, C3B atoms adopt a chair conformation, whereas the five-membered chelate rings involving C1A, C4A and C1B, C4B assume a gauche conformation (Min & Suh, 2001; Kim et al., 2015).

Supra­molecular features top

The S atoms of the thio­cyanate groups form inter­molecular N—H···S hydrogen bonds with adjacent secondary amine groups of the aza­macrocyclic ligand, giving rise to two symmetry-independent one-dimensional polymeric chains propagating along the b-axis direction (Fig. 2 and Table 1).

Database survey top

A search of the Cambridge Structural Database (Version 5.36, Feb 2015 with two updates; Groom & Allen, 2014) indicated one complex of NiII with the same aza­maclocyclic ligand having an anionic tetra­zole derivative at the axial positions (Kim et al., 2015).

Synthesis and crystallization top

The title compound (I) was prepared as follows. The starting complex, [Ni(C16H38N6)](ClO4)2, was prepared by a slightly modified method reported by Jung et al. (1989). To a MeCN solution (10 mL) of [Ni(C16H38N6)] (ClO4)2 (0.15 g, 0.26 mmol) was slowly added a MeCN solution (5 mL) containing sodium thio­cyanate (0.042 g, 0.52 mmol) at room temperature. A pale-pink precipitate was formed, which was filtered off, washed with MeCN, and di­ethyl ether, and dried in air. Single crystals of the title compound were obtained by layering of the MeCN solution of sodium thio­cyanate on the MeCN solution of [Ni(C16H38N6)] (ClO4)2 for several days. Yield: 0.062 g (49%). FT–IR (KBr, cm-1): 3304, 3243, 2929, 2867, 2069, 1468, 1386, 1273, 1204, 1070, 925.

Safety note: Although we have experienced no problem with the compounds reported in this study, perchlorate salts of metal complexes are often explosive and should be handled with great caution.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.98–0.99 Å and an N–H distance of 1.0 Å with Uiso(H) values of 1.2 or 1.5Ueq of the parent atoms. The C7A and C8A atoms of the macrocyclic ligand were refined as disordered over two sets of sites (C71A, C72A and C81A, C82A) with refined occupancies of 0.630 and 0.370, respectively. The bond distances and angles of the disordered part were restrained to ensure proper geometry using DFIX and DANG instructions of SHELXL2014/7 (Sheldrick, 2015b).

Related literature top

For related literature, see: Bradforth et al. (1993); Groom & Allen (2014); Halcrow (2013); Jung et al. (1989); Kim et al. (2015); Lehn (1995); Min & Suh (2001); Ryoo et al. (2010); Safarifard & Morsali (2012); Shen et al. (2012); Shin et al. (2010); Steed & Atwood (2009); Suh et al. (2012); Wang & Wang (2015); Zhou et al. (2012).

Structure description top

Coordination compounds, including those formed by macrocyclic ligands, have attracted wide inter­est of material sciences, because of their potential applications (Lehn, 1995; Zhou et al., 2012). In particular, NiII macrocyclic complexes having vacant sites in the axial positions have been used for the synthesis of new supra­molecular materials with inter­esting properties, including chiral recognition (Ryoo et al., 2010) and gas storage (Suh et al., 2012). For example, NiII complexes with alkyl-substituted tetra-aza­macrocyclic ligands and anionic tetra­zole derivatives, metal cyanide and azide (Shen et al., 2012; Kim et al., 2015) have been studied as magnetic materials and substrates for crystal engineering. The thio­cyanate ion is a versatile anionic ligand which can easily bind to a transition metal ion as a terminal or bridging ligand through the nitro­gen and/or the sulfur atoms, thus allowing the assembly of multi-dimensional compounds or heterometallic complexes (Safarifard & Morsali, 2012; Wang & Wang 2015). Here, we report the synthesis and crystal structure of an NiII complex with aza­macrocycle and two thio­cyanate anions, trans-(1,8-di­butyl-1,3,6,8,10,13-hexa­aza­cyclo­tetra­decane-κ4N3,N6,N10,N13)bis­(thio­cyanato-κN)nickel(II) (I).

The title compound (I) contains two crystallographically independent complex molecules that are centrosymmetric. Each NiII ion lies on an inversion centre and is coordinated by four secondary amine N atoms of the aza­macrocyclic ligand in a square-planar fashion in the equatorial plane, and by two N atoms from the thio­cyanate anions at the axial positions, resulting in a tetra­gonally distorted o­cta­hedral geometry, as shown in Fig. 1. The average equatorial bond lengths, Ni1A—Neq and Ni1B—Neq, are 2.070 (1) and 2.070 (1) Å, respectively. The axial bond lengths, Ni1A—Nax and Ni1B—Nax are 2.119 (1) and 2.093 (1) Å, respectively. The axial bonds are longer than the equatorial bonds, which can be attributed either to a large Jahn–Teller distortion effect of the NiII ion and/or to a ring contraction of the aza­macrocyclic ligand (Halcrow, 2013; Kim et al., 2015). The average N—C and C—S bond lengths of the coordinated thio­cyanate ions are 1.157 (1) and 1.627 (1) Å, respectively. The former is very similar to a C≡N triple-bond distance, while the latter is slightly shorter than reported C—S single-bond distances (Bradforth et al., 1993; Shin et al., 2010). The six-membered chelate rings involving C2A, C3A and C2B, C3B atoms adopt a chair conformation, whereas the five-membered chelate rings involving C1A, C4A and C1B, C4B assume a gauche conformation (Min & Suh, 2001; Kim et al., 2015).

The S atoms of the thio­cyanate groups form inter­molecular N—H···S hydrogen bonds with adjacent secondary amine groups of the aza­macrocyclic ligand, giving rise to two symmetry-independent one-dimensional polymeric chains propagating along the b-axis direction (Fig. 2 and Table 1).

A search of the Cambridge Structural Database (Version 5.36, Feb 2015 with two updates; Groom & Allen, 2014) indicated one complex of NiII with the same aza­maclocyclic ligand having an anionic tetra­zole derivative at the axial positions (Kim et al., 2015).

For related literature, see: Bradforth et al. (1993); Groom & Allen (2014); Halcrow (2013); Jung et al. (1989); Kim et al. (2015); Lehn (1995); Min & Suh (2001); Ryoo et al. (2010); Safarifard & Morsali (2012); Shen et al. (2012); Shin et al. (2010); Steed & Atwood (2009); Suh et al. (2012); Wang & Wang (2015); Zhou et al. (2012).

Synthesis and crystallization top

The title compound (I) was prepared as follows. The starting complex, [Ni(C16H38N6)](ClO4)2, was prepared by a slightly modified method reported by Jung et al. (1989). To a MeCN solution (10 mL) of [Ni(C16H38N6)] (ClO4)2 (0.15 g, 0.26 mmol) was slowly added a MeCN solution (5 mL) containing sodium thio­cyanate (0.042 g, 0.52 mmol) at room temperature. A pale-pink precipitate was formed, which was filtered off, washed with MeCN, and di­ethyl ether, and dried in air. Single crystals of the title compound were obtained by layering of the MeCN solution of sodium thio­cyanate on the MeCN solution of [Ni(C16H38N6)] (ClO4)2 for several days. Yield: 0.062 g (49%). FT–IR (KBr, cm-1): 3304, 3243, 2929, 2867, 2069, 1468, 1386, 1273, 1204, 1070, 925.

Safety note: Although we have experienced no problem with the compounds reported in this study, perchlorate salts of metal complexes are often explosive and should be handled with great caution.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.98–0.99 Å and an N–H distance of 1.0 Å with Uiso(H) values of 1.2 or 1.5Ueq of the parent atoms. The C7A and C8A atoms of the macrocyclic ligand were refined as disordered over two sets of sites (C71A, C72A and C81A, C82A) with refined occupancies of 0.630 and 0.370, respectively. The bond distances and angles of the disordered part were restrained to ensure proper geometry using DFIX and DANG instructions of SHELXL2014/7 (Sheldrick, 2015b).

Computing details top

Data collection: PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983); cell refinement: HKL3000sm (Otwinowski & Minor, 1997); data reduction: HKL3000sm (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Putz & Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the title compound, showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. The minor position of the n-butyl substituent in the A molecule is not shown.
[Figure 2] Fig. 2. View of the crystal packing, with N—H···S hydrogen bonds drawn as red dashed lines. H atoms have been omitted for clarity.
trans-(1,8-Dibutyl-1,3,6,8,10,13-hexaazacyclotetradecane-κ4N3,N6,N10,N13)bis(thiocyanato-κN)nickel(II) top
Crystal data top
[Ni(NCS)2(C16H38N6)]Z = 2
Mr = 489.39F(000) = 524
Triclinic, P1Dx = 1.348 Mg m−3
a = 8.6610 (17) ÅSynchrotron radiation, λ = 0.630 Å
b = 12.027 (2) ÅCell parameters from 49914 reflections
c = 12.560 (3) Åθ = 0.4–33.6°
α = 94.66 (3)°µ = 0.72 mm−1
β = 97.99 (3)°T = 180 K
γ = 110.04 (3)°Block, pale pink
V = 1205.4 (5) Å30.25 × 0.15 × 0.13 mm
Data collection top
ADSC Q210 CCD area-detector
diffractometer		6243 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnetRint = 0.014
ω scanθmax = 26.0°, θmin = 1.6°
Absorption correction: empirical (using intensity measurements)
(HKL3000sm SCALEPACK; Otwinowski & Minor, 1997)		h = −12→12
Tmin = 0.841, Tmax = 0.916k = −16→16
12812 measured reflectionsl = −17→17
6583 independent reflections
Refinement top
Refinement on F211 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0541P)2 + 0.7946P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
6583 reflectionsΔρmax = 1.58 e Å−3
287 parametersΔρmin = −1.11 e Å−3
Crystal data top
[Ni(NCS)2(C16H38N6)]γ = 110.04 (3)°
Mr = 489.39V = 1205.4 (5) Å3
Triclinic, P1Z = 2
a = 8.6610 (17) ÅSynchrotron radiation, λ = 0.630 Å
b = 12.027 (2) ŵ = 0.72 mm−1
c = 12.560 (3) ÅT = 180 K
α = 94.66 (3)°0.25 × 0.15 × 0.13 mm
β = 97.99 (3)°
Data collection top
ADSC Q210 CCD area-detector
diffractometer		6583 independent reflections
Absorption correction: empirical (using intensity measurements)
(HKL3000sm SCALEPACK; Otwinowski & Minor, 1997)		6243 reflections with I > 2σ(I)
Tmin = 0.841, Tmax = 0.916Rint = 0.014
12812 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04211 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.06Δρmax = 1.58 e Å−3
6583 reflectionsΔρmin = −1.11 e Å−3
287 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni1A0.00000.00000.50000.02295 (8)
S1A−0.39772 (6)0.09973 (6)0.68745 (4)0.05126 (15)
N1A0.20720 (17)0.11708 (13)0.60541 (11)0.0301 (3)
H1A0.30830.10690.58280.036*
N2A0.02319 (18)0.10693 (13)0.37714 (12)0.0321 (3)
H2A0.11050.09550.33770.039*
N3A0.2318 (2)0.27979 (15)0.49597 (17)0.0460 (4)
N4A−0.16012 (18)0.07346 (14)0.56843 (13)0.0343 (3)
C1A0.1944 (2)0.07739 (18)0.71320 (14)0.0373 (4)
H1A10.11280.10360.74590.045*
H1A20.30420.11290.76210.045*
C2A0.2242 (3)0.24393 (17)0.60232 (18)0.0426 (4)
H2A10.12800.25670.62850.051*
H2A20.32690.29570.65280.051*
C3A0.0780 (3)0.23584 (17)0.41904 (19)0.0431 (4)
H3A10.09160.28210.35710.052*
H3A2−0.01060.24990.45390.052*
C4A−0.1381 (2)0.05792 (19)0.30124 (15)0.0387 (4)
H4A1−0.12510.08720.23040.046*
H4A2−0.22230.08400.33070.046*
C5A0.3770 (3)0.2784 (3)0.4483 (3)0.0632 (7)
H5A10.37050.30950.37780.076*
H5A20.36930.19450.43320.076*
C6A0.5445 (3)0.3493 (3)0.5164 (4)0.0870 (11)
H6A10.56220.31310.58290.104*
H6A20.55340.43270.53780.104*
C71A0.6816 (5)0.3457 (6)0.4395 (4)0.084 (2)0.63
H71A0.67810.26280.42330.100*0.63
H71B0.65630.37470.37010.100*0.63
C81A0.8493 (5)0.4237 (4)0.4995 (4)0.0654 (11)0.63
H81A0.84830.50350.52130.098*0.63
H81B0.93240.42960.45250.098*0.63
H81C0.87800.38950.56420.098*0.63
C72A0.7095 (11)0.3319 (9)0.5052 (9)0.077 (2)0.37
H72A0.80050.37820.56620.093*0.37
H72B0.69710.24650.49910.093*0.37
C82A0.7346 (11)0.3790 (12)0.4057 (7)0.090 (3)0.37
H82A0.64980.32540.34610.135*0.37
H82B0.84600.38570.39210.135*0.37
H82C0.72550.45820.41070.135*0.37
C9A−0.2607 (2)0.08368 (15)0.61628 (13)0.0304 (3)
Ni2B1.00000.50000.00000.02474 (8)
S1B0.48562 (7)0.51503 (7)−0.18976 (6)0.0654 (2)
N1B0.90438 (18)0.33335 (13)−0.09357 (12)0.0319 (3)
H1B0.79100.3226−0.13380.038*
N2B0.86585 (17)0.44340 (13)0.12179 (11)0.0293 (3)
H2B0.74930.44040.09790.035*
N3B0.7849 (2)0.23013 (14)0.05324 (14)0.0368 (3)
N4B0.79629 (19)0.53663 (16)−0.07763 (14)0.0384 (3)
C1B1.0161 (2)0.34041 (17)−0.17379 (16)0.0395 (4)
H1B10.96140.2749−0.23500.047*
H1B21.12100.3322−0.13940.047*
C2B0.8871 (3)0.23310 (16)−0.02905 (18)0.0401 (4)
H2B10.83770.1568−0.07890.048*
H2B20.99970.23920.00650.048*
C3B0.8572 (2)0.32257 (17)0.14559 (15)0.0363 (3)
H3B10.97150.32580.17350.044*
H3B20.79040.30080.20370.044*
C4B0.9457 (2)0.53919 (17)0.21515 (14)0.0366 (4)
H4B11.05030.53210.25150.044*
H4B20.87000.53200.26850.044*
C5B0.6079 (2)0.20371 (17)0.00919 (15)0.0366 (4)
H5B10.57180.1390−0.05300.044*
H5B20.59560.2756−0.01840.044*
C6B0.4936 (2)0.16605 (17)0.09165 (15)0.0382 (4)
H6B10.51430.09970.12530.046*
H6B20.52060.23400.14980.046*
C7B0.3107 (3)0.12633 (19)0.04111 (16)0.0413 (4)
H7B10.27940.0511−0.00890.050*
H7B20.29320.1877−0.00200.050*
C8B0.1979 (3)0.1066 (2)0.12585 (18)0.0456 (4)
H8B10.22120.05080.17250.068*
H8B20.08080.07340.08950.068*
H8B30.21900.18310.17010.068*
C9B0.6659 (2)0.52684 (14)−0.12328 (13)0.0294 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni1A0.02036 (13)0.02643 (14)0.02328 (13)0.00930 (10)0.00718 (9)0.00057 (9)
S1A0.0351 (2)0.0888 (4)0.0415 (3)0.0343 (3)0.01563 (19)0.0052 (3)
N1A0.0239 (6)0.0347 (7)0.0292 (6)0.0085 (5)0.0064 (5)−0.0031 (5)
N2A0.0294 (6)0.0369 (7)0.0333 (7)0.0130 (5)0.0111 (5)0.0087 (5)
N3A0.0402 (8)0.0320 (7)0.0611 (11)0.0053 (6)0.0126 (8)0.0082 (7)
N4A0.0292 (6)0.0389 (7)0.0376 (7)0.0161 (6)0.0098 (5)−0.0021 (6)
C1A0.0309 (8)0.0535 (10)0.0258 (7)0.0150 (7)0.0046 (6)−0.0020 (7)
C2A0.0391 (9)0.0315 (8)0.0492 (10)0.0061 (7)0.0071 (8)−0.0078 (7)
C3A0.0437 (10)0.0344 (9)0.0555 (11)0.0155 (8)0.0138 (8)0.0144 (8)
C4A0.0354 (8)0.0551 (11)0.0305 (8)0.0204 (8)0.0076 (6)0.0118 (7)
C5A0.0370 (11)0.0618 (15)0.0824 (18)−0.0004 (10)0.0211 (11)0.0257 (13)
C6A0.0414 (13)0.0560 (16)0.147 (3)−0.0010 (11)0.0047 (17)0.0253 (19)
C71A0.042 (2)0.129 (4)0.055 (2)−0.011 (2)0.0025 (17)0.067 (3)
C81A0.051 (2)0.062 (2)0.076 (3)0.0168 (18)0.0036 (19)−0.003 (2)
C72A0.062 (5)0.074 (5)0.098 (7)0.026 (4)0.016 (5)0.019 (5)
C82A0.083 (7)0.129 (10)0.054 (5)0.049 (7)−0.015 (5)−0.011 (6)
C9A0.0253 (7)0.0374 (8)0.0300 (7)0.0144 (6)0.0043 (5)−0.0002 (6)
Ni2B0.02097 (13)0.02802 (14)0.02616 (14)0.01142 (10)0.00207 (9)0.00079 (10)
S1B0.0371 (3)0.0927 (5)0.0605 (4)0.0332 (3)−0.0185 (2)−0.0201 (3)
N1B0.0280 (6)0.0312 (6)0.0350 (7)0.0090 (5)0.0090 (5)−0.0017 (5)
N2B0.0241 (6)0.0333 (6)0.0283 (6)0.0093 (5)0.0025 (5)0.0009 (5)
N3B0.0358 (7)0.0314 (7)0.0425 (8)0.0102 (6)0.0093 (6)0.0065 (6)
N4B0.0285 (7)0.0482 (9)0.0418 (8)0.0189 (6)0.0019 (6)0.0083 (7)
C1B0.0345 (8)0.0373 (9)0.0424 (9)0.0079 (7)0.0145 (7)−0.0086 (7)
C2B0.0419 (9)0.0297 (8)0.0524 (11)0.0152 (7)0.0153 (8)0.0037 (7)
C3B0.0341 (8)0.0393 (9)0.0347 (8)0.0119 (7)0.0039 (6)0.0102 (7)
C4B0.0299 (8)0.0446 (9)0.0289 (7)0.0070 (7)0.0060 (6)−0.0040 (7)
C5B0.0354 (8)0.0332 (8)0.0363 (8)0.0054 (6)0.0084 (7)0.0042 (6)
C6B0.0386 (9)0.0371 (8)0.0339 (8)0.0067 (7)0.0089 (7)0.0046 (7)
C7B0.0397 (9)0.0445 (10)0.0339 (8)0.0069 (8)0.0105 (7)0.0029 (7)
C8B0.0434 (10)0.0489 (11)0.0440 (10)0.0125 (8)0.0158 (8)0.0083 (8)
C9B0.0283 (7)0.0303 (7)0.0309 (7)0.0131 (6)0.0055 (6)0.0003 (6)
Geometric parameters (Å, º) top
Ni1A—N1Ai2.0640 (17)C82A—H82A0.9800
Ni1A—N1A2.0640 (17)C82A—H82B0.9800
Ni1A—N2Ai2.0754 (15)C82A—H82C0.9800
Ni1A—N2A2.0754 (15)Ni2B—N2Bii2.0675 (15)
Ni1A—N4Ai2.1190 (15)Ni2B—N2B2.0675 (15)
Ni1A—N4A2.1190 (15)Ni2B—N1Bii2.0719 (16)
S1A—C9A1.6339 (17)Ni2B—N1B2.0719 (16)
N1A—C1A1.478 (2)Ni2B—N4Bii2.0933 (16)
N1A—C2A1.486 (2)Ni2B—N4B2.0933 (16)
N1A—H1A1.0000S1B—C9B1.6190 (18)
N2A—C4A1.477 (2)N1B—C1B1.479 (2)
N2A—C3A1.483 (3)N1B—C2B1.484 (2)
N2A—H2A1.0000N1B—H1B1.0000
N3A—C3A1.436 (3)N2B—C4B1.480 (2)
N3A—C2A1.440 (3)N2B—C3B1.486 (2)
N3A—C5A1.470 (3)N2B—H2B1.0000
N4A—C9A1.158 (2)N3B—C3B1.444 (3)
C1A—C4Ai1.517 (3)N3B—C2B1.446 (2)
C1A—H1A10.9900N3B—C5B1.469 (3)
C1A—H1A20.9900N4B—C9B1.156 (2)
C2A—H2A10.9900C1B—C4Bii1.523 (3)
C2A—H2A20.9900C1B—H1B10.9900
C3A—H3A10.9900C1B—H1B20.9900
C3A—H3A20.9900C2B—H2B10.9900
C4A—C1Ai1.517 (3)C2B—H2B20.9900
C4A—H4A10.9900C3B—H3B10.9900
C4A—H4A20.9900C3B—H3B20.9900
C5A—C6A1.501 (4)C4B—C1Bii1.522 (3)
C5A—H5A10.9900C4B—H4B10.9900
C5A—H5A20.9900C4B—H4B20.9900
C6A—C72A1.537 (9)C5B—C6B1.520 (3)
C6A—C71A1.641 (6)C5B—H5B10.9900
C6A—H6A10.9900C5B—H5B20.9900
C6A—H6A20.9900C6B—C7B1.514 (3)
C71A—C81A1.485 (5)C6B—H6B10.9900
C71A—H71A0.9900C6B—H6B20.9900
C71A—H71B0.9900C7B—C8B1.522 (3)
C81A—H81A0.9800C7B—H7B10.9900
C81A—H81B0.9800C7B—H7B20.9900
C81A—H81C0.9800C8B—H8B10.9800
C72A—C82A1.427 (12)C8B—H8B20.9800
C72A—H72A0.9900C8B—H8B30.9800
C72A—H72B0.9900
N1Ai—Ni1A—N1A180.00 (7)C72A—C82A—H82B109.5
N1Ai—Ni1A—N2Ai95.00 (7)H82A—C82A—H82B109.5
N1A—Ni1A—N2Ai85.00 (6)C72A—C82A—H82C109.5
N1Ai—Ni1A—N2A85.00 (6)H82A—C82A—H82C109.5
N1A—Ni1A—N2A95.00 (6)H82B—C82A—H82C109.5
N2Ai—Ni1A—N2A180.00 (8)N4A—C9A—S1A178.09 (16)
N1Ai—Ni1A—N4Ai91.75 (6)N2Bii—Ni2B—N2B180.0
N1A—Ni1A—N4Ai88.25 (6)N2Bii—Ni2B—N1Bii93.91 (6)
N2Ai—Ni1A—N4Ai92.85 (6)N2B—Ni2B—N1Bii86.09 (6)
N2A—Ni1A—N4Ai87.15 (6)N2Bii—Ni2B—N1B86.09 (6)
N1Ai—Ni1A—N4A88.25 (6)N2B—Ni2B—N1B93.91 (6)
N1A—Ni1A—N4A91.75 (6)N1Bii—Ni2B—N1B180.0
N2Ai—Ni1A—N4A87.15 (6)N2Bii—Ni2B—N4Bii88.26 (6)
N2A—Ni1A—N4A92.85 (6)N2B—Ni2B—N4Bii91.74 (6)
N4Ai—Ni1A—N4A180.0N1Bii—Ni2B—N4Bii88.42 (7)
C1A—N1A—C2A114.56 (15)N1B—Ni2B—N4Bii91.58 (7)
C1A—N1A—Ni1A106.14 (11)N2Bii—Ni2B—N4B91.74 (6)
C2A—N1A—Ni1A112.51 (12)N2B—Ni2B—N4B88.26 (6)
C1A—N1A—H1A107.8N1Bii—Ni2B—N4B91.58 (7)
C2A—N1A—H1A107.8N1B—Ni2B—N4B88.42 (7)
Ni1A—N1A—H1A107.8N4Bii—Ni2B—N4B180.0
C4A—N2A—C3A115.13 (15)C1B—N1B—C2B114.04 (15)
C4A—N2A—Ni1A105.93 (11)C1B—N1B—Ni2B104.88 (11)
C3A—N2A—Ni1A112.70 (12)C2B—N1B—Ni2B113.56 (11)
C4A—N2A—H2A107.6C1B—N1B—H1B108.0
C3A—N2A—H2A107.6C2B—N1B—H1B108.0
Ni1A—N2A—H2A107.6Ni2B—N1B—H1B108.0
C3A—N3A—C2A116.46 (17)C4B—N2B—C3B114.37 (14)
C3A—N3A—C5A113.3 (2)C4B—N2B—Ni2B104.95 (10)
C2A—N3A—C5A116.6 (2)C3B—N2B—Ni2B112.98 (11)
C9A—N4A—Ni1A161.18 (15)C4B—N2B—H2B108.1
N1A—C1A—C4Ai108.32 (14)C3B—N2B—H2B108.1
N1A—C1A—H1A1110.0Ni2B—N2B—H2B108.1
C4Ai—C1A—H1A1110.0C3B—N3B—C2B115.91 (15)
N1A—C1A—H1A2110.0C3B—N3B—C5B115.92 (16)
C4Ai—C1A—H1A2110.0C2B—N3B—C5B113.83 (16)
H1A1—C1A—H1A2108.4C9B—N4B—Ni2B163.23 (16)
N3A—C2A—N1A113.64 (16)N1B—C1B—C4Bii108.49 (15)
N3A—C2A—H2A1108.8N1B—C1B—H1B1110.0
N1A—C2A—H2A1108.8C4Bii—C1B—H1B1110.0
N3A—C2A—H2A2108.8N1B—C1B—H1B2110.0
N1A—C2A—H2A2108.8C4Bii—C1B—H1B2110.0
H2A1—C2A—H2A2107.7H1B1—C1B—H1B2108.4
N3A—C3A—N2A113.85 (16)N3B—C2B—N1B113.94 (15)
N3A—C3A—H3A1108.8N3B—C2B—H2B1108.8
N2A—C3A—H3A1108.8N1B—C2B—H2B1108.8
N3A—C3A—H3A2108.8N3B—C2B—H2B2108.8
N2A—C3A—H3A2108.8N1B—C2B—H2B2108.8
H3A1—C3A—H3A2107.7H2B1—C2B—H2B2107.7
N2A—C4A—C1Ai108.23 (15)N3B—C3B—N2B114.19 (14)
N2A—C4A—H4A1110.1N3B—C3B—H3B1108.7
C1Ai—C4A—H4A1110.1N2B—C3B—H3B1108.7
N2A—C4A—H4A2110.1N3B—C3B—H3B2108.7
C1Ai—C4A—H4A2110.1N2B—C3B—H3B2108.7
H4A1—C4A—H4A2108.4H3B1—C3B—H3B2107.6
N3A—C5A—C6A115.5 (3)N2B—C4B—C1Bii108.66 (15)
N3A—C5A—H5A1108.4N2B—C4B—H4B1110.0
C6A—C5A—H5A1108.4C1Bii—C4B—H4B1110.0
N3A—C5A—H5A2108.4N2B—C4B—H4B2110.0
C6A—C5A—H5A2108.4C1Bii—C4B—H4B2110.0
H5A1—C5A—H5A2107.5H4B1—C4B—H4B2108.3
C5A—C6A—C72A125.6 (5)N3B—C5B—C6B113.59 (16)
C5A—C6A—C71A105.5 (3)N3B—C5B—H5B1108.8
C5A—C6A—H6A1110.6C6B—C5B—H5B1108.8
C71A—C6A—H6A1110.6N3B—C5B—H5B2108.8
C5A—C6A—H6A2110.6C6B—C5B—H5B2108.8
C71A—C6A—H6A2110.6H5B1—C5B—H5B2107.7
H6A1—C6A—H6A2108.8C7B—C6B—C5B112.38 (16)
C81A—C71A—C6A107.8 (4)C7B—C6B—H6B1109.1
C81A—C71A—H71A110.2C5B—C6B—H6B1109.1
C6A—C71A—H71A110.2C7B—C6B—H6B2109.1
C81A—C71A—H71B110.2C5B—C6B—H6B2109.1
C6A—C71A—H71B110.2H6B1—C6B—H6B2107.9
H71A—C71A—H71B108.5C6B—C7B—C8B112.29 (17)
C71A—C81A—H81A109.5C6B—C7B—H7B1109.1
C71A—C81A—H81B109.5C8B—C7B—H7B1109.1
H81A—C81A—H81B109.5C6B—C7B—H7B2109.1
C71A—C81A—H81C109.5C8B—C7B—H7B2109.1
H81A—C81A—H81C109.5H7B1—C7B—H7B2107.9
H81B—C81A—H81C109.5C7B—C8B—H8B1109.5
C82A—C72A—C6A99.0 (7)C7B—C8B—H8B2109.5
C82A—C72A—H72A112.0H8B1—C8B—H8B2109.5
C6A—C72A—H72A112.0C7B—C8B—H8B3109.5
C82A—C72A—H72B112.0H8B1—C8B—H8B3109.5
C6A—C72A—H72B112.0H8B2—C8B—H8B3109.5
H72A—C72A—H72B109.6N4B—C9B—S1B178.44 (17)
C72A—C82A—H82A109.5
C2A—N1A—C1A—C4Ai167.05 (14)C5A—C6A—C72A—C82A71.8 (8)
Ni1A—N1A—C1A—C4Ai42.27 (15)C2B—N1B—C1B—C4Bii−167.20 (15)
C3A—N3A—C2A—N1A73.7 (2)Ni2B—N1B—C1B—C4Bii−42.36 (16)
C5A—N3A—C2A—N1A−64.4 (2)C3B—N3B—C2B—N1B−71.3 (2)
C1A—N1A—C2A—N3A−178.39 (15)C5B—N3B—C2B—N1B66.9 (2)
Ni1A—N1A—C2A—N3A−57.03 (18)C1B—N1B—C2B—N3B176.89 (15)
C2A—N3A—C3A—N2A−73.1 (2)Ni2B—N1B—C2B—N3B56.80 (19)
C5A—N3A—C3A—N2A66.4 (2)C2B—N3B—C3B—N2B72.1 (2)
C4A—N2A—C3A—N3A177.61 (16)C5B—N3B—C3B—N2B−65.2 (2)
Ni1A—N2A—C3A—N3A55.96 (19)C4B—N2B—C3B—N3B−177.77 (14)
C3A—N2A—C4A—C1Ai−167.20 (15)Ni2B—N2B—C3B—N3B−57.79 (17)
Ni1A—N2A—C4A—C1Ai−41.95 (15)C3B—N2B—C4B—C1Bii166.62 (14)
C3A—N3A—C5A—C6A166.0 (2)Ni2B—N2B—C4B—C1Bii42.25 (15)
C2A—N3A—C5A—C6A−54.7 (3)C3B—N3B—C5B—C6B−58.2 (2)
N3A—C5A—C6A—C72A159.1 (5)C2B—N3B—C5B—C6B163.62 (16)
N3A—C5A—C6A—C71A−173.6 (3)N3B—C5B—C6B—C7B−173.67 (16)
C5A—C6A—C71A—C81A175.0 (4)C5B—C6B—C7B—C8B−171.39 (18)
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+2, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···S1Aiii1.002.733.5154 (17)136
N2B—H2B···S1Biv1.002.663.4556 (17)137
Symmetry codes: (iii) x+1, y, z; (iv) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···S1Ai1.002.733.5154 (17)135.6
N2B—H2B···S1Bii1.002.663.4556 (17)137.0
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Ni(NCS)2(C16H38N6)]
Mr489.39
Crystal system, space groupTriclinic, P1
Temperature (K)180
a, b, c (Å)8.6610 (17), 12.027 (2), 12.560 (3)
α, β, γ (°)94.66 (3), 97.99 (3), 110.04 (3)
V (Å3)1205.4 (5)
Z2
Radiation typeSynchrotron, λ = 0.630 Å
µ (mm−1)0.72
Crystal size (mm)0.25 × 0.15 × 0.13
Data collection
DiffractometerADSC Q210 CCD area-detector
Absorption correctionEmpirical (using intensity measurements)
(HKL3000sm SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.841, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections		12812, 6583, 6243
Rint0.014
(sin θ/λ)max (Å−1)0.696
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.111, 1.06
No. of reflections6583
No. of parameters287
No. of restraints11
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.58, −1.11

Computer programs: PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983), HKL3000sm (Otwinowski & Minor, 1997), SHELXT2014 (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Putz & Brandenburg, 2007), publCIF (Westrip, 2010).

 

Acknowledgements

This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (NRF-2014R1A1A2058815) and supported by the Institute for Basic Science (IBS, IBS-R007-D1–2015 − a01). The X-ray crystallography BL2D-SMC beamline at PLS-II was supported in part by MSIP and POSTECH.

References

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ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages 779-782
doi:10.1107/S205698901501110X
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