{(S)-2-[({2-[1-(Anthracen-9-ylmeth­yl)pyrrolidine-2-carboxamido]­phen­yl}(phen­yl)methyl­idene)amino]­acetato(2−)-κ4N,N′,N′′,O1}nickel(II)

Padělková, Z.; Popkov, A.; Nádvorník, M.

doi:10.1107/S1600536812026827

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m954-m955

https://doi.org/10.1107/S1600536812026827

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{(S)-2-[({2-[1-(Anthracen-9-ylmethyl)pyrrolidine-2-carboxamido]phenyl}(phenyl)methylidene)amino]acetato(2−)-κ⁴N,N′,N′′,O¹}nickel(II)

Zdeňka Padělková,^a ^* Alexander Popkov ^b and Milan Nádvorník ^a

^aDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 53210 Pardubice, Czech Republic, and ^bNa Klínku 1082, 530 06 Pardubice, Czech Republic
^*Correspondence e-mail: zdenka.padelkova@upce.cz

(Received 14 May 2012; accepted 13 June 2012; online 20 June 2012)

The title compound, [Ni(C₃₅H₂₉N₃O₃)], includes a Schiff base ligand derived from (S)-1-[(anthracen-9-yl)methyl]-N-(2-benzoylphenyl)pyrrolidine-2-carboxamide and glycine. The Ni^II atom is coordinated by three N atoms [Ni—N = 1.937 (3), 1.850 (3) and 1.850 (3) Å] and one O atom [Ni—O = 1.859 (2) Å], resulting in a pseudo-square-planar coordination environment.

Related literature

For preparation and evaluation of similar compounds in model reactions, see: Belokon et al. (1988 ); Kožíšek et al. (2004 ); Popkov et al. (2002 , 2010 ). For an overview of application procedures, see: Popkov et al. (2005 ) and works cited therein. For NMR in solutions and similar highly unusual long-range spin–spin interactions, see: Jirman et al. (1998 ); Langer et al. (2007 ); Popkov et al. (1998 , 2003 ). For the review of applications in positron emission tomography (PET), see: Popkov & De Spiegeleer (2012 ).

Experimental

Crystal data

[Ni(C₃₅H₂₉N₃O₃)]
M_r = 598.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.9080 (5) Å
b = 16.5249 (12) Å
c = 18.6981 (13) Å
V = 2752.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 150 K
0.31 × 0.26 × 0.14 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction: Gaussian (Coppens, 1970 ) T_min = 0.856, T_max = 0.925
23768 measured reflections
6120 independent reflections
5037 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.087
S = 1.19
6120 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ), 2615 Friedel pairs
Flack parameter: −0.019 (14)

Data collection: COLLECT (Hooft, 1998 ) and DENZO (Otwinowski & Minor, 1997 ); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812026827/im2378sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026827/im2378Isup2.hkl

checkCIF report

Comment top

Preparation of carbon-11 and fluorine-18 labelled amino acids for positron emission tomography (PET) is a big challenge for radiochemists. Due to time constrains brought by short half-life of the both isotopes, chromatographic separation steps should be avoided in PET radiosyntheses unless absolutely necessary (Popkov & De Spiegeleer (2012)). In order to meet this requirement we have been developing enantiospecific and highly enantioselective amino acid synthons based on Belokon's nickel(II) complexes (Belokon, et al., 1988). We already demonstrated the origin of the high stereoselectivity of the incorporation of amino acid side chains into these synthons. Intramolecular electrostatic interaction of the (substituted) benzyl ring and the nickel atom (Kožíšek et al., 2004) play a very important role as well as steric shielding by ortho-substituents of the benzyl ring (Popkov, et al., 2002). In this communication we describe the crystal structure of the nickel(II) complex with an electron-rich (9-antracenyl)methyl substituent at the nitrogen atom of the proline residue due to the fact that the Schiff base ligand was derived from (S)-N-(2-benzoylphenyl)1-(9-antracenyl)methylpyrrolidine-2-carboxamide and glycine (AMGK). This structure is a candidate for charge density measurement. Recently, we have shown such complexes to be very efficient synthons of glycine or alanine for the preparation of radiotracers for PET (Popkov et al., 2010). Similar complexes demonstrated highly unusual long-range spin-spin interactions in ¹³C-¹³C and ¹⁵N-¹³C NMR spectra (Jirman et al., 1998; Popkov et al., 1998; Langer et al., 2007). These interactions have been attributed to the influence of a diffuse electron cloud from the benzyl group (Popkov et al., 2003). We expect such interactions to be more pronounced in AMGK. For the future charge density measurement it is important that the conformation of AMGK described in this communication is similar to the conformation of the Ni^II complex of Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and glycine (GK) (Popkov et al., 2003) which is the simplest complex in this class and which was comprehensively studied by diffraction of X-rays and by NMR in solutions (Popkov et al., 1998; Kožíšek et al., 2004). In the solid state both complexes exhibit no intra- or intermolecular hydrogen bonds. The crystal packing is therefore only determined by weak interactions. Packing of the molecules in both crystals as well as the conformations are very similar, although the conformations of the molecules themselves differ. In the [Ni(GK)] complex intramolecular interactions are weaker as exemplified by the distance Ni-C22 (2.9282 (17) Å) and the angles Ni-N1-C21 (107.53 (9)°) and N1-C21-C22 (114.04 (13)°), respectively. In the complex [Ni(AMGK)] (Fig. 1) much stronger intramolecular interactions are observed shown by the distance Ni-C22 (3.181 (3) Å) and the angles Ni-N1-C21 (111.82 (19)°) and N1-C21-C22 (114.9 (2)°). Bulkiness of the anthranylmethyl group practically does not change the conformation of the molecule. The interatomic distance Ni-C22 in the more sterically hindered complex is just 0.253Å longer which is not too big difference compared to the published data for (substituted) analogues of GK (Popkov et al. (2003)). MP2 ab initio modelling of the interactions is in progress.

Related literature top

For preparation and evaluation of similar compounds in model reactions, see: Belokon et al. (1988); Kožíšek et al. (2004); Popkov et al. (2002, 2010). For an overview of application procedures, see: Popkov et al. (2005) and works cited therein. For NMR in solutions and similar highly unusual long-range spin–spin interactions, see: Jirman et al. (1998); Langer et al. (2007); Popkov et al. (1998, 2003). For the review of applications in positron emission tomography (PET), see: Popkov & De Spiegeleer (2012).

Experimental top

The title compound has been prepared according to a procedure described elsewhere (Popkov et al., 2010). Crystals suitable for the measurement were obtained by slow evaporation of the solvent from a solution of the title compound in toluene/methanol (2:1).

Structure description top

For preparation and evaluation of similar compounds in model reactions, see: Belokon et al. (1988); Kožíšek et al. (2004); Popkov et al. (2002, 2010). For an overview of application procedures, see: Popkov et al. (2005) and works cited therein. For NMR in solutions and similar highly unusual long-range spin–spin interactions, see: Jirman et al. (1998); Langer et al. (2007); Popkov et al. (1998, 2003). For the review of applications in positron emission tomography (PET), see: Popkov & De Spiegeleer (2012).

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compounds with displacement ellipsoids shown at the 50% probability level. H atoms are shown as spheres with arbitrary radii.

{(S)-2-[({2-[1-(Anthracen-9-ylmethyl)pyrrolidine-2- carboxamido]phenyl}(phenyl)methylidene)amino]acetato(2-)- κ⁴N,N',N'',O¹}nickel(II) top

Crystal data top

[Ni(C₃₅H₂₉N₃O₃)]	F(000) = 1248
M_r = 598.32	D_x = 1.444 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23827 reflections
a = 8.9080 (5) Å	θ = 1–27.5°
b = 16.5249 (12) Å	µ = 0.75 mm⁻¹
c = 18.6981 (13) Å	T = 150 K
V = 2752.4 (3) Å³	Block, red
Z = 4	0.31 × 0.26 × 0.14 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	6120 independent reflections
Radiation source: fine-focus sealed tube	5037 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 1.6°
φ and ω scans to fill the Ewald sphere	h = −11→10
Absorption correction: gaussian (Coppens, 1970)	k = −19→21
T_min = 0.856, T_max = 0.925	l = −22→24
23768 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0124P)² + 2.2393P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max = 0.001
6120 reflections	Δρ_max = 0.32 e Å⁻³
379 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2615 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.019 (14)

Crystal data top

[Ni(C₃₅H₂₉N₃O₃)]	V = 2752.4 (3) Å³
M_r = 598.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.9080 (5) Å	µ = 0.75 mm⁻¹
b = 16.5249 (12) Å	T = 150 K
c = 18.6981 (13) Å	0.31 × 0.26 × 0.14 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	6120 independent reflections
Absorption correction: gaussian (Coppens, 1970)	5037 reflections with I > 2σ(I)
T_min = 0.856, T_max = 0.925	R_int = 0.071
23768 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.32 e Å⁻³
S = 1.19	Δρ_min = −0.38 e Å⁻³
6120 reflections	Absolute structure: Flack (1983), 2615 Friedel pairs
379 parameters	Absolute structure parameter: −0.019 (14)
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
Ni1	0.24182 (5)	0.29142 (2)	0.341302 (19)	0.01922 (9)
O2	0.3360 (2)	0.30227 (14)	0.42952 (11)	0.0254 (5)
N3	0.0779 (3)	0.34255 (16)	0.38193 (14)	0.0205 (6)
N1	0.4180 (3)	0.24291 (16)	0.29833 (14)	0.0210 (6)
N2	0.1482 (3)	0.27289 (15)	0.25450 (14)	0.0211 (6)
O3	0.2972 (2)	0.34356 (15)	0.54199 (12)	0.0308 (6)
O1	0.1528 (3)	0.17305 (14)	0.16634 (15)	0.0376 (6)
C7	−0.0029 (4)	0.3172 (2)	0.15323 (19)	0.0258 (7)
H7	0.0546	0.2854	0.1227	0.031*
C14	−0.2558 (4)	0.36460 (18)	0.43374 (16)	0.0243 (6)
H14	−0.2499	0.3085	0.4308	0.029*
C5	0.2084 (3)	0.2090 (2)	0.21725 (17)	0.0246 (7)
C20	0.2548 (4)	0.33210 (17)	0.48055 (15)	0.0226 (6)
C18	−0.1673 (4)	0.4966 (2)	0.3992 (2)	0.0295 (8)
H18	−0.1027	0.5289	0.3726	0.035*
C12	−0.0396 (3)	0.37223 (18)	0.34982 (18)	0.0210 (7)
C13	−0.1571 (4)	0.41254 (19)	0.39428 (17)	0.0210 (7)
C6	0.0284 (4)	0.3172 (2)	0.22744 (18)	0.0216 (7)
C21	0.5180 (3)	0.3056 (2)	0.26366 (17)	0.0249 (7)
H21A	0.5682	0.3362	0.3009	0.030*
H21B	0.5947	0.2777	0.2364	0.030*
C4	0.3570 (4)	0.18159 (19)	0.24694 (18)	0.0248 (7)
H4	0.4284	0.1733	0.2078	0.030*
C22	0.4380 (4)	0.3641 (2)	0.21447 (18)	0.0258 (8)
C2	0.4126 (4)	0.1213 (2)	0.36427 (19)	0.0315 (8)
H2A	0.3359	0.1345	0.3992	0.038*
H2B	0.4709	0.0757	0.3816	0.038*
C15	−0.3628 (4)	0.4004 (2)	0.47780 (19)	0.0300 (8)
H15	−0.4290	0.3684	0.5039	0.036*
C11	−0.0600 (4)	0.36713 (19)	0.27272 (17)	0.0210 (7)
C9	−0.2021 (4)	0.4135 (2)	0.16876 (19)	0.0297 (8)
H9	−0.2780	0.4452	0.1493	0.036*
C1	0.5114 (3)	0.1935 (2)	0.34910 (18)	0.0258 (7)
H1A	0.5331	0.2235	0.3925	0.031*
H1B	0.6051	0.1771	0.3270	0.031*
C16	−0.3702 (4)	0.4840 (2)	0.4825 (2)	0.0352 (9)
H16	−0.4409	0.5080	0.5123	0.042*
C8	−0.1158 (4)	0.3641 (2)	0.12543 (19)	0.0291 (8)
H8	−0.1348	0.3628	0.0765	0.035*
C30	0.3486 (5)	0.4049 (2)	0.0956 (2)	0.0354 (9)
C10	−0.1745 (4)	0.4141 (2)	0.24071 (19)	0.0262 (7)
H10	−0.2332	0.4471	0.2697	0.031*
C24	0.3850 (5)	0.4572 (2)	0.3174 (2)	0.0379 (10)
H24	0.4428	0.4251	0.3476	0.045*
C35	0.4320 (4)	0.3507 (2)	0.13999 (18)	0.0276 (8)
C19	0.0938 (4)	0.3502 (2)	0.45967 (17)	0.0264 (8)
H19A	0.0265	0.3128	0.4835	0.032*
H19B	0.0678	0.4047	0.4743	0.032*
C34	0.5118 (4)	0.2865 (3)	0.10405 (19)	0.0364 (8)
H34	0.5675	0.2500	0.1310	0.044*
C28	0.2807 (4)	0.4858 (2)	0.1981 (2)	0.0341 (9)
C23	0.3690 (4)	0.4337 (2)	0.2440 (2)	0.0283 (8)
C3	0.3427 (4)	0.1027 (2)	0.2911 (2)	0.0319 (8)
H3A	0.2380	0.0877	0.2963	0.038*
H3B	0.3956	0.0586	0.2679	0.038*
C17	−0.2732 (5)	0.5318 (2)	0.4430 (2)	0.0355 (9)
H17	−0.2786	0.5878	0.4464	0.043*
C25	0.3180 (5)	0.5244 (2)	0.3438 (3)	0.0540 (12)
H25	0.3341	0.5394	0.3911	0.065*
C33	0.5074 (5)	0.2784 (3)	0.0321 (2)	0.0535 (12)
H33	0.5601	0.2363	0.0107	0.064*
C31	0.3485 (6)	0.3928 (3)	0.0199 (2)	0.0557 (13)
H31	0.2938	0.4279	−0.0089	0.067*
C29	0.2727 (5)	0.4695 (2)	0.1259 (2)	0.0407 (10)
H29	0.2140	0.5025	0.0969	0.049*
C26	0.2233 (6)	0.5723 (3)	0.2992 (3)	0.0592 (15)
H26	0.1728	0.6165	0.3183	0.071*
C27	0.2067 (4)	0.5540 (2)	0.2292 (3)	0.0501 (12)
H27	0.1455	0.5864	0.2009	0.060*
C32	0.4254 (6)	0.3324 (3)	−0.0107 (2)	0.0650 (15)
H32	0.4247	0.3262	−0.0601	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02184 (17)	0.02218 (17)	0.01363 (16)	0.0019 (2)	−0.00030 (18)	−0.00127 (17)
O2	0.0269 (11)	0.0340 (14)	0.0153 (11)	0.0000 (11)	−0.0023 (9)	−0.0030 (11)
N3	0.0244 (14)	0.0227 (14)	0.0145 (14)	0.0016 (11)	0.0007 (11)	−0.0004 (11)
N1	0.0241 (14)	0.0218 (14)	0.0170 (14)	0.0009 (11)	0.0001 (11)	−0.0008 (11)
N2	0.0273 (14)	0.0218 (15)	0.0144 (13)	0.0023 (11)	−0.0034 (11)	−0.0012 (11)
O3	0.0336 (14)	0.0419 (15)	0.0170 (12)	−0.0017 (11)	−0.0014 (9)	−0.0034 (11)
O1	0.0482 (14)	0.0312 (13)	0.0334 (15)	0.0079 (11)	−0.0156 (13)	−0.0145 (12)
C7	0.0321 (17)	0.0277 (18)	0.0176 (17)	0.0001 (14)	−0.0030 (15)	−0.0016 (15)
C14	0.0232 (15)	0.0272 (15)	0.0225 (15)	−0.0020 (17)	−0.0029 (16)	0.0003 (12)
C5	0.0318 (18)	0.0224 (15)	0.0197 (15)	0.0027 (15)	−0.0005 (12)	−0.0036 (15)
C20	0.0284 (15)	0.0231 (14)	0.0162 (14)	0.0000 (17)	0.0001 (17)	0.0004 (11)
C18	0.0340 (19)	0.0246 (18)	0.030 (2)	0.0003 (16)	0.0079 (16)	0.0028 (16)
C12	0.0255 (15)	0.0153 (15)	0.0220 (18)	−0.0023 (13)	0.0019 (13)	0.0014 (14)
C13	0.0231 (16)	0.0236 (17)	0.0162 (16)	0.0008 (14)	−0.0005 (13)	0.0021 (13)
C6	0.0266 (17)	0.0208 (17)	0.0173 (17)	−0.0006 (13)	0.0010 (13)	−0.0006 (13)
C21	0.0230 (16)	0.032 (2)	0.0196 (17)	−0.0019 (15)	0.0011 (12)	−0.0032 (15)
C4	0.0278 (17)	0.0281 (18)	0.0184 (17)	0.0051 (14)	−0.0005 (14)	−0.0070 (14)
C22	0.0250 (17)	0.030 (2)	0.0228 (18)	−0.0053 (15)	0.0019 (14)	0.0034 (15)
C2	0.045 (2)	0.0235 (19)	0.026 (2)	0.0072 (16)	0.0020 (15)	0.0050 (14)
C15	0.0225 (17)	0.045 (2)	0.0225 (19)	−0.0059 (16)	0.0019 (14)	0.0027 (16)
C11	0.0227 (16)	0.0197 (17)	0.0206 (17)	−0.0029 (13)	−0.0010 (13)	0.0024 (13)
C9	0.0333 (18)	0.0305 (18)	0.025 (2)	0.0022 (14)	−0.0065 (14)	0.0060 (16)
C1	0.0287 (15)	0.0320 (19)	0.0165 (16)	0.0092 (14)	−0.0006 (13)	−0.0007 (15)
C16	0.0296 (19)	0.048 (2)	0.028 (2)	0.0051 (17)	0.0049 (16)	−0.0073 (18)
C8	0.037 (2)	0.032 (2)	0.0185 (17)	0.0005 (16)	−0.0059 (14)	0.0037 (15)
C30	0.044 (2)	0.032 (2)	0.029 (2)	−0.0119 (18)	−0.0077 (17)	0.0065 (17)
C10	0.0266 (17)	0.0279 (18)	0.0241 (19)	0.0023 (14)	0.0015 (14)	0.0037 (15)
C24	0.051 (2)	0.031 (2)	0.032 (2)	−0.0039 (18)	0.0139 (18)	−0.0006 (17)
C35	0.0278 (17)	0.035 (2)	0.0197 (19)	−0.0051 (15)	0.0012 (13)	0.0035 (14)
C19	0.0296 (18)	0.034 (2)	0.0156 (17)	0.0082 (15)	0.0003 (13)	−0.0015 (14)
C34	0.042 (2)	0.045 (2)	0.0228 (19)	−0.004 (2)	0.0042 (15)	−0.0018 (19)
C28	0.030 (2)	0.0249 (18)	0.047 (2)	−0.0092 (15)	0.0032 (17)	0.0067 (16)
C23	0.0252 (17)	0.0260 (18)	0.034 (2)	−0.0071 (15)	0.0066 (15)	0.0019 (16)
C3	0.033 (2)	0.0241 (18)	0.039 (2)	0.0053 (16)	−0.0028 (16)	−0.0011 (16)
C17	0.043 (2)	0.0275 (17)	0.037 (2)	0.0073 (18)	0.0062 (18)	−0.0041 (15)
C25	0.080 (3)	0.038 (2)	0.043 (3)	−0.004 (2)	0.029 (3)	−0.006 (2)
C33	0.070 (3)	0.062 (3)	0.028 (2)	−0.003 (3)	0.010 (2)	−0.008 (2)
C31	0.080 (3)	0.061 (3)	0.025 (2)	−0.013 (3)	−0.018 (2)	0.015 (2)
C29	0.042 (2)	0.035 (2)	0.046 (2)	−0.008 (2)	−0.013 (2)	0.0141 (17)
C26	0.067 (4)	0.033 (2)	0.077 (4)	0.005 (2)	0.039 (3)	−0.002 (2)
C27	0.041 (3)	0.033 (2)	0.076 (4)	−0.0018 (18)	0.014 (2)	0.013 (2)
C32	0.103 (4)	0.076 (4)	0.015 (2)	−0.019 (3)	−0.008 (2)	0.001 (2)

Geometric parameters (Å, º) top

Ni1—N2	1.850 (3)	C15—H15	0.9300
Ni1—N3	1.850 (3)	C11—C10	1.415 (4)
Ni1—O2	1.859 (2)	C9—C10	1.368 (5)
Ni1—N1	1.937 (3)	C9—C8	1.383 (5)
O2—C20	1.295 (4)	C9—H9	0.9300
N3—C12	1.303 (4)	C1—H1A	0.9701
N3—C19	1.466 (4)	C1—H1B	0.9700
N1—C4	1.499 (4)	C16—C17	1.384 (5)
N1—C1	1.503 (4)	C16—H16	0.9300
N1—C21	1.512 (4)	C8—H8	0.9300
N2—C5	1.374 (4)	C30—C29	1.385 (6)
N2—C6	1.389 (4)	C30—C35	1.429 (5)
O3—C20	1.224 (4)	C30—C31	1.431 (6)
O1—C5	1.226 (4)	C10—H10	0.9300
C7—C8	1.372 (5)	C24—C25	1.354 (5)
C7—C6	1.415 (5)	C24—C23	1.433 (5)
C7—H7	0.9300	C24—H24	0.9299
C14—C15	1.392 (5)	C35—C34	1.442 (5)
C14—C13	1.395 (4)	C19—H19A	0.9701
C14—H14	0.9299	C19—H19B	0.9701
C5—C4	1.505 (4)	C34—C33	1.353 (5)
C20—C19	1.516 (5)	C34—H34	0.9301
C18—C17	1.378 (5)	C28—C29	1.379 (5)
C18—C13	1.394 (5)	C28—C27	1.429 (6)
C18—H18	0.9300	C28—C23	1.447 (5)
C12—C11	1.455 (4)	C3—H3A	0.9701
C12—C13	1.493 (4)	C3—H3B	0.9700
C6—C11	1.421 (4)	C17—H17	0.9299
C21—C22	1.513 (5)	C25—C26	1.426 (7)
C21—H21A	0.9700	C25—H25	0.9300
C21—H21B	0.9700	C33—C32	1.403 (7)
C4—C3	1.548 (5)	C33—H33	0.9300
C4—H4	0.9800	C31—C32	1.339 (7)
C22—C35	1.411 (5)	C31—H31	0.9300
C22—C23	1.417 (5)	C29—H29	0.9300
C2—C1	1.511 (5)	C26—C27	1.350 (7)
C2—C3	1.534 (5)	C26—H26	0.9300
C2—H2A	0.9701	C27—H27	0.9300
C2—H2B	0.9701	C32—H32	0.9300
C15—C16	1.386 (5)

N2—Ni1—N3	94.59 (12)	C10—C9—H9	120.7
N2—Ni1—O2	176.00 (11)	C8—C9—H9	120.5
N3—Ni1—O2	87.01 (11)	N1—C1—C2	103.0 (3)
N2—Ni1—N1	86.14 (11)	N1—C1—H1A	111.2
N3—Ni1—N1	177.26 (12)	C2—C1—H1A	111.3
O2—Ni1—N1	92.43 (11)	N1—C1—H1B	111.1
C20—O2—Ni1	116.0 (2)	C2—C1—H1B	111.1
C12—N3—C19	120.2 (3)	H1A—C1—H1B	109.2
C12—N3—Ni1	128.1 (2)	C17—C16—C15	120.4 (3)
C19—N3—Ni1	111.7 (2)	C17—C16—H16	119.9
C4—N1—C1	103.8 (2)	C15—C16—H16	119.8
C4—N1—C21	113.7 (3)	C7—C8—C9	121.2 (3)
C1—N1—C21	108.4 (2)	C7—C8—H8	119.5
C4—N1—Ni1	104.59 (19)	C9—C8—H8	119.2
C1—N1—Ni1	114.3 (2)	C29—C30—C35	120.0 (3)
C21—N1—Ni1	111.8 (2)	C29—C30—C31	120.8 (4)
C5—N2—C6	121.3 (3)	C35—C30—C31	119.2 (4)
C5—N2—Ni1	113.3 (2)	C9—C10—C11	122.8 (3)
C6—N2—Ni1	125.3 (2)	C9—C10—H10	118.5
C8—C7—C6	121.1 (3)	C11—C10—H10	118.7
C8—C7—H7	119.4	C25—C24—C23	121.8 (4)
C6—C7—H7	119.6	C25—C24—H24	119.4
C15—C14—C13	120.2 (3)	C23—C24—H24	118.8
C15—C14—H14	119.8	C22—C35—C30	119.6 (3)
C13—C14—H14	120.0	C22—C35—C34	123.8 (3)
O1—C5—N2	127.5 (3)	C30—C35—C34	116.5 (3)
O1—C5—C4	119.7 (3)	N3—C19—C20	109.3 (3)
N2—C5—C4	112.8 (3)	N3—C19—H19A	110.0
O3—C20—O2	125.3 (3)	C20—C19—H19A	109.9
O3—C20—C19	120.2 (3)	N3—C19—H19B	109.7
O2—C20—C19	114.4 (3)	C20—C19—H19B	109.6
C17—C18—C13	120.3 (3)	H19A—C19—H19B	108.3
C17—C18—H18	119.9	C33—C34—C35	121.5 (4)
C13—C18—H18	119.8	C33—C34—H34	119.4
N3—C12—C11	122.3 (3)	C35—C34—H34	119.2
N3—C12—C13	118.3 (3)	C29—C28—C27	121.9 (4)
C11—C12—C13	119.3 (3)	C29—C28—C23	119.6 (4)
C18—C13—C14	119.3 (3)	C27—C28—C23	118.5 (4)
C18—C13—C12	121.8 (3)	C22—C23—C24	123.3 (3)
C14—C13—C12	118.9 (3)	C22—C23—C28	119.2 (3)
N2—C6—C7	120.6 (3)	C24—C23—C28	117.5 (3)
N2—C6—C11	121.0 (3)	C2—C3—C4	105.9 (3)
C7—C6—C11	118.3 (3)	C2—C3—H3A	110.6
N1—C21—C22	114.9 (3)	C4—C3—H3A	110.4
N1—C21—H21A	108.8	C2—C3—H3B	110.5
C22—C21—H21A	108.6	C4—C3—H3B	110.7
N1—C21—H21B	108.4	H3A—C3—H3B	108.7
C22—C21—H21B	108.4	C18—C17—C16	120.2 (3)
H21A—C21—H21B	107.5	C18—C17—H17	119.7
N1—C4—C5	110.6 (3)	C16—C17—H17	120.0
N1—C4—C3	104.9 (3)	C24—C25—C26	120.1 (5)
C5—C4—C3	112.2 (3)	C24—C25—H25	119.8
N1—C4—H4	109.7	C26—C25—H25	120.0
C5—C4—H4	109.7	C34—C33—C32	121.3 (5)
C3—C4—H4	109.6	C34—C33—H33	119.2
C35—C22—C23	119.7 (3)	C32—C33—H33	119.5
C35—C22—C21	121.2 (3)	C32—C31—C30	121.8 (4)
C23—C22—C21	119.1 (3)	C32—C31—H31	119.1
C1—C2—C3	103.1 (3)	C30—C31—H31	119.1
C1—C2—H2A	111.0	C28—C29—C30	121.7 (4)
C3—C2—H2A	111.1	C28—C29—H29	119.1
C1—C2—H2B	111.3	C30—C29—H29	119.3
C3—C2—H2B	111.1	C27—C26—C25	120.5 (4)
H2A—C2—H2B	109.1	C27—C26—H26	119.7
C16—C15—C14	119.6 (3)	C25—C26—H26	119.8
C16—C15—H15	120.2	C26—C27—C28	121.4 (4)
C14—C15—H15	120.2	C26—C27—H27	119.2
C10—C11—C6	117.8 (3)	C28—C27—H27	119.5
C10—C11—C12	118.5 (3)	C31—C32—C33	119.8 (4)
C6—C11—C12	123.7 (3)	C31—C32—H32	120.1
C10—C9—C8	118.8 (3)	C33—C32—H32	120.1

Experimental details

Crystal data
Chemical formula	[Ni(C₃₅H₂₉N₃O₃)]
M_r	598.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	8.9080 (5), 16.5249 (12), 18.6981 (13)
V (Å³)	2752.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.31 × 0.26 × 0.14

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector
Absorption correction	Gaussian (Coppens, 1970)
T_min, T_max	0.856, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	23768, 6120, 5037
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.087, 1.19
No. of reflections	6120
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.38
Absolute structure	Flack (1983), 2615 Friedel pairs
Absolute structure parameter	−0.019 (14)

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

ZP and MN would like to thank the Faculty of Chemical Technology, University of Pardubice, for financial support of this work.

References

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