[2-((R)-{2-[(S)-1-Benzylpyrrolidin-2-ylcarbonylazanidyl]­phen­yl}(phen­yl)methyl­idene­amino)-4-hy­droxy­butano­ato-κ4N,N′,N′′,O1]nickel(II) toluene disolvate

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

doi:10.1107/S1600536811031059

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1258-m1259

doi:10.1107/S1600536811031059

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[2-((R)-{2-[(S)-1-Benzylpyrrolidin-2-ylcarbonylazanidyl]phenyl}(phenyl)methylideneamino)-4-hydroxybutanoato-κ⁴N,N′,N′′,O¹]nickel(II) toluene disolvate

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 ^bDepartment of Chemistry and Environmental Technology, Faculty of Technology, Tomas Bata University in Zlín, nám T. G. Masaryka 275, 762 72 Zlín, Czech Republic
^*Correspondence e-mail: milan.nadvornik@upce.cz

(Received 14 July 2011; accepted 2 August 2011; online 17 August 2011)

The central Ni atom in the title compound, [Ni(C₂₉H₂₉N₃O₄)]·2C₇H₈, is coordinated in a distorted square-planar environment by three N atoms [Ni—N = 1.942 (3), 1.843 (3) and 1.853 (3) Å] and one O atom [1.868 (3) Å] of the tetradentate ligand. The conformation of the hydroxybutanoate side chain is controlled by an intermolecular hydrogen bond.

Related literature

For the synthesis of similar complexes and their potential use as radiotracers, see: Bourdier et al. (2011 ); Fasth & Långström (1990 ); Kožíšek et al. (2004 ); Langer et al. (2007 ); Popkov & Breza (2010 ); Popkov et al. (2005 , 2008 , 2010 ); Nádvorník et al. (2008 ).

Experimental

Crystal data

[Ni(C₂₉H₂₉N₃O₄)]·2C₇H₈
M_r = 726.53
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.2660 (14) Å
b = 12.8570 (9) Å
c = 24.527 (3) Å
V = 3552.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 150 K
0.36 × 0.23 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction: gaussian (Coppens, 1970 ) T_min = 0.852, T_max = 0.924
21133 measured reflections
7165 independent reflections
6170 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.142
S = 1.01
7165 reflections
461 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.44 e Å⁻³
Absolute structure: Flack (1983 ), 3089 Friedel pairs
Flack parameter: 0.000 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	1.94	2.720 (5)	159
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+2]$ .

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: 10.1107/S1600536811031059/im2308sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031059/im2308Isup2.hkl

checkCIF report

Comment top

Substituted Ni(II) complexes of Schiff bases derived from (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and α-amino acids are intermediates for the synthesis of radiotracers for positron emission tomography (Fasth & Långström 1990, Popkov et al., 2010). In the search for efficient and cheap radiotracers new approaches employing ω-labelled amino acids are being developed (Bourdier et al., 2011). We published the first structure of a complex bearing a hydroxy group in ω-position of the amino acid fragment side chain (Popkov et al., 2008), which was used for MP2 modelling and topological QTAIM analysis of reactivity of the complexes in alkylation reactions (Popkov & Breza, 2010). The absolute configuration of the chiral centres of this diastereomer is SS. Due to our interest in chiral nickel (II) complexes suitable for charge density studies (Kožíšek et al., 2004), we intended to compare charge densities of two diastereomers of the same complex. In this communication we describe structure of the SR-diastereomer {2-[(R)-({2-(S)-1- benzylpyrrolidine-2-carboxamido]phenyl}(phenyl)methyleneamino]-4- hydroxybutanoato-κN-4,N',N'',O} nickel(II) (Ni(II) complex of the Schiff base from (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and (R)-2-amino-4-hydroxybutanoic acid), which is a candidate for charge density measurement. Structures of the two diastereomers differ a lot. Like in complexes derived from quaternary α-amino acids (Langer et al., 2007) in the SR-diastereomer steric repulsion of the benzyl group and the side chain is very strong. It compensates steric factors which distort the coordination plane of the SS-complex and the SR-complex is approaching an ideal square-planar coordination. Unlike the SS -diastereomer where the hydrogen bond O4—H4AW···O3 is intramolecular, in the SR-complex a bond O2—H2···O3 is intermolecular. In both diastereomers the benzyl group is in apical position towards the nickel atom.

Related literature top

For the synthesis of similar complexes and their potential use as radiotracers, see: Bourdier et al. (2011); Fasth & Långström (1990); Kožíšek et al. (2004); Langer et al. (2007); Popkov & Breza (2010); Popkov et al. (2005, 2008, 2010); Nádvorník et al. (2008).

Experimental top

{2-[(R)-({2-(S)-1-benzylpyrrolidine-2-carboxamido]phenyl}(phenyl)methyleneamino]-4-hydroxybutanoato-κN-4,N',N'',O} nickel(II) was chromatographically isolated as the minor diastereomer (4% yield) in the synthesis of {2-[(S)-({2-(S)-1-benzylpyrrolidine-2-carboxamido]phenyl} (phenyl)methylene)amino]-4-hydroxybutanoato-κN-4,N',N'',O} nickel(II) (Popkov et al., 2008). Crystals suitable for X-ray diffraction were prepared by crystallization from toluene-methanol (2:1) by slow evaporation at room temperature.

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. View of the title compound with displacement ellipsoids shown at the 50% probability level. H atoms are shown with arbitrary radii.
	Fig. 2. View of the motif of the crystal structure with hydrogen bonds indicated as dashed lines.

[2-((R)-{2-[(S)-1-Benzylpyrrolidin-2- ylcarbonylazanidyl]phenyl}(phenyl)methylideneamino)-4-hydroxybutanoato- κ⁴N,N',N'',O¹]nickel(II) toluene disolvate top

Crystal data top

[Ni(C₂₉H₂₉N₃O₄)]·2C₇H₈	F(000) = 1536
M_r = 726.53	D_x = 1.358 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 21280 reflections
a = 11.2660 (14) Å	θ = 1–26.5°
b = 12.8570 (9) Å	µ = 0.60 mm⁻¹
c = 24.527 (3) Å	T = 150 K
V = 3552.7 (6) Å³	Block, red
Z = 4	0.36 × 0.23 × 0.20 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	7165 independent reflections
Radiation source: fine-focus sealed tube	6170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.5°, θ_min = 2.0°
ϕ and ω scans to fill the Ewald sphere	h = −13→14
Absorption correction: gaussian (Coppens, 1970)	k = −15→16
T_min = 0.852, T_max = 0.924	l = −27→30
21133 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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0456P)² + 5.8181P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
7165 reflections	Δρ_max = 0.41 e Å⁻³
461 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 3089 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (17)

Crystal data top

[Ni(C₂₉H₂₉N₃O₄)]·2C₇H₈	V = 3552.7 (6) Å³
M_r = 726.53	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.2660 (14) Å	µ = 0.60 mm⁻¹
b = 12.8570 (9) Å	T = 150 K
c = 24.527 (3) Å	0.36 × 0.23 × 0.20 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	7165 independent reflections
Absorption correction: gaussian (Coppens, 1970)	6170 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.924	R_int = 0.103
21133 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.142	Δρ_max = 0.41 e Å⁻³
S = 1.01	Δρ_min = −0.44 e Å⁻³
7165 reflections	Absolute structure: Flack (1983), 3089 Friedel pairs
461 parameters	Absolute structure parameter: 0.000 (17)
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	0.41796 (4)	0.96012 (4)	0.967796 (19)	0.02409 (13)
O4	0.4291 (3)	1.1043 (2)	0.97576 (11)	0.0313 (6)
N3	0.5515 (3)	0.9687 (3)	0.92463 (12)	0.0243 (6)
N1	0.2795 (3)	0.9604 (3)	1.01498 (12)	0.0276 (7)
N2	0.4009 (3)	0.8177 (2)	0.95941 (13)	0.0254 (7)
C12	0.5905 (4)	0.9023 (3)	0.88878 (14)	0.0252 (8)
C22	0.4189 (4)	0.9437 (3)	1.09551 (14)	0.0308 (9)
C5	0.3250 (4)	0.7761 (3)	0.99831 (16)	0.0292 (9)
C28	0.7135 (3)	1.0520 (3)	0.97481 (17)	0.0287 (8)
H28A	0.7561	0.9891	0.9652	0.034*
H28B	0.6782	1.0410	1.0104	0.034*
O3	0.5443 (3)	1.2393 (2)	0.95379 (13)	0.0366 (7)
O1	0.3252 (3)	0.6883 (2)	1.01642 (12)	0.0355 (7)
C20	0.5239 (4)	1.1452 (3)	0.95497 (16)	0.0297 (9)
C4	0.2299 (4)	0.8524 (3)	1.01382 (16)	0.0285 (9)
H4	0.1964	0.8344	1.0495	0.034*
C9	0.5605 (4)	0.6291 (4)	0.83845 (17)	0.0336 (10)
H9	0.5933	0.5884	0.8110	0.040*
C19	0.6139 (3)	1.0688 (3)	0.93337 (16)	0.0250 (8)
H19	0.6468	1.0939	0.8988	0.030*
C23	0.5277 (4)	0.9944 (4)	1.09517 (18)	0.0384 (11)
H23	0.5328	1.0594	1.0787	0.046*
C21	0.3124 (4)	0.9958 (3)	1.07169 (16)	0.0330 (10)
H21A	0.2453	0.9836	1.0956	0.040*
H21B	0.3268	1.0702	1.0709	0.040*
C11	0.5450 (4)	0.7964 (3)	0.88514 (15)	0.0255 (8)
C6	0.4583 (3)	0.7542 (3)	0.92145 (15)	0.0250 (8)
C8	0.4775 (4)	0.5876 (3)	0.87468 (18)	0.0349 (10)
H8	0.4549	0.5183	0.8715	0.042*
C13	0.6839 (4)	0.9361 (3)	0.84898 (16)	0.0278 (9)
O2	0.8883 (3)	1.1086 (3)	1.01775 (18)	0.0631 (12)
H2	0.9414	1.1522	1.0182	0.076*
C7	0.4286 (4)	0.6479 (3)	0.91515 (17)	0.0323 (9)
H7	0.3744	0.6182	0.9391	0.039*
C18	0.8040 (4)	0.9271 (4)	0.85954 (17)	0.0359 (10)
H18	0.8300	0.8955	0.8915	0.043*
C3	0.1311 (4)	0.8533 (4)	0.97001 (19)	0.0373 (10)
H3A	0.0555	0.8329	0.9856	0.045*
H3B	0.1502	0.8061	0.9404	0.045*
C27	0.4135 (5)	0.8469 (4)	1.12086 (16)	0.0364 (10)
H27	0.3416	0.8114	1.1218	0.044*
C10	0.5920 (4)	0.7317 (3)	0.84435 (15)	0.0304 (8)
H10	0.6476	0.7593	0.8204	0.037*
C2	0.1265 (5)	0.9646 (5)	0.94919 (19)	0.0473 (12)
H2A	0.0451	0.9855	0.9423	0.057*
H2B	0.1718	0.9723	0.9158	0.057*
C14	0.6456 (4)	0.9796 (4)	0.79975 (16)	0.0384 (11)
H14	0.5648	0.9843	0.7923	0.046*
C25	0.6204 (4)	0.8544 (4)	1.14307 (18)	0.0402 (11)
H25	0.6874	0.8240	1.1584	0.048*
C1	0.1801 (4)	1.0286 (4)	0.99426 (18)	0.0382 (10)
H1A	0.2103	1.0943	0.9806	0.046*
H1B	0.1225	1.0421	1.0228	0.046*
C15	0.7278 (5)	1.0161 (4)	0.7621 (2)	0.0490 (13)
H15	0.7022	1.0449	0.7294	0.059*
C26	0.5126 (5)	0.8026 (4)	1.14463 (19)	0.0405 (11)
H26	0.5067	0.7381	1.1616	0.049*
C17	0.8863 (4)	0.9650 (4)	0.82149 (18)	0.0422 (11)
H17	0.9672	0.9609	0.8288	0.051*
C32	0.8207 (5)	0.5005 (5)	0.7516 (2)	0.0555 (14)
H32	0.8700	0.5559	0.7608	0.067*
C31	0.7956 (7)	0.4249 (5)	0.7887 (2)	0.0687 (18)
H31	0.8328	0.4267	0.8226	0.082*
C16	0.8479 (5)	1.0092 (4)	0.7733 (2)	0.0502 (14)
H16	0.9027	1.0348	0.7483	0.060*
C24	0.6281 (5)	0.9516 (5)	1.11859 (19)	0.0475 (12)
H24	0.6996	0.9876	1.1179	0.057*
C29	0.7998 (5)	1.1393 (4)	0.9789 (2)	0.0536 (15)
H29A	0.7602	1.2023	0.9908	0.064*
H29B	0.8361	1.1523	0.9437	0.064*
C30	0.7161 (6)	0.3442 (5)	0.7772 (2)	0.0616 (16)
C35	0.6702 (6)	0.3399 (5)	0.7253 (3)	0.0666 (17)
H35	0.6196	0.2857	0.7158	0.080*
C33	0.7705 (6)	0.4941 (5)	0.6997 (2)	0.0623 (16)
H33	0.7887	0.5437	0.6734	0.075*
C34	0.6963 (6)	0.4156 (6)	0.6886 (3)	0.0674 (18)
H34	0.6629	0.4119	0.6539	0.081*
C42	0.7867 (9)	0.7455 (5)	0.6131 (3)	0.078 (2)
H42	0.7321	0.7470	0.5847	0.094*
C38	0.8331 (8)	0.7707 (5)	0.7070 (3)	0.076 (2)
H38	0.8089	0.7879	0.7420	0.092*
C39	0.9515 (8)	0.7540 (6)	0.6966 (3)	0.081 (2)
H39	1.0061	0.7560	0.7250	0.097*
C41	0.9073 (9)	0.7280 (5)	0.6024 (3)	0.082 (2)
H41	0.9318	0.7110	0.5674	0.098*
C37	0.7498 (8)	0.7643 (5)	0.6665 (3)	0.074 (2)
C40	0.9906 (8)	0.7345 (6)	0.6443 (3)	0.084 (2)
H40	1.0710	0.7251	0.6373	0.101*
C36	0.6855 (11)	0.2664 (8)	0.8205 (3)	0.120 (4)
H36A	0.7492	0.2173	0.8240	0.144*
H36B	0.6744	0.3020	0.8545	0.144*
H36C	0.6138	0.2303	0.8110	0.144*
C43	0.6229 (9)	0.7779 (9)	0.6775 (4)	0.113 (3)
H43A	0.6125	0.8359	0.7017	0.136*
H43B	0.5812	0.7909	0.6441	0.136*
H43C	0.5920	0.7162	0.6943	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0244 (2)	0.0219 (2)	0.0260 (2)	−0.0005 (2)	0.0026 (2)	−0.0001 (2)
O4	0.0314 (15)	0.0260 (13)	0.0366 (15)	−0.0005 (13)	0.0081 (14)	−0.0015 (12)
N3	0.0293 (17)	0.0172 (14)	0.0264 (14)	0.0012 (14)	−0.0020 (12)	−0.0002 (13)
N1	0.0286 (16)	0.0262 (16)	0.0278 (15)	0.0026 (16)	−0.0002 (12)	−0.0028 (15)
N2	0.0241 (17)	0.0251 (16)	0.0269 (16)	−0.0012 (14)	0.0002 (14)	0.0004 (13)
C12	0.0227 (18)	0.0280 (19)	0.0249 (17)	0.0030 (17)	−0.0036 (16)	0.0019 (15)
C22	0.033 (2)	0.036 (2)	0.0242 (17)	0.000 (2)	0.0026 (17)	−0.0118 (16)
C5	0.029 (2)	0.034 (2)	0.0252 (19)	−0.0097 (19)	0.0021 (16)	−0.0007 (17)
C28	0.0259 (18)	0.0228 (19)	0.037 (2)	−0.0020 (16)	0.0009 (16)	−0.0007 (18)
O3	0.0333 (15)	0.0251 (14)	0.0513 (18)	−0.0014 (13)	0.0081 (13)	0.0002 (13)
O1	0.0424 (17)	0.0281 (15)	0.0361 (16)	−0.0066 (14)	0.0027 (13)	0.0037 (12)
C20	0.028 (2)	0.028 (2)	0.033 (2)	0.0009 (17)	0.0005 (16)	0.0019 (17)
C4	0.0244 (19)	0.032 (2)	0.0289 (19)	−0.0059 (18)	0.0058 (16)	0.0022 (17)
C9	0.030 (2)	0.036 (2)	0.034 (2)	0.0021 (19)	−0.0030 (17)	−0.0102 (18)
C19	0.027 (2)	0.0195 (18)	0.0288 (18)	−0.0062 (15)	0.0059 (15)	0.0010 (14)
C23	0.042 (3)	0.043 (3)	0.031 (2)	−0.006 (2)	0.0013 (19)	−0.0049 (19)
C21	0.034 (2)	0.034 (2)	0.030 (2)	−0.0008 (19)	0.0052 (18)	−0.0081 (17)
C11	0.0265 (19)	0.0271 (19)	0.0227 (17)	−0.0013 (16)	−0.0039 (15)	0.0017 (15)
C6	0.0222 (17)	0.0238 (19)	0.0289 (19)	−0.0008 (16)	−0.0035 (15)	−0.0009 (16)
C8	0.034 (2)	0.030 (2)	0.041 (2)	−0.0021 (19)	−0.0030 (19)	−0.0095 (19)
C13	0.032 (2)	0.0209 (19)	0.0301 (19)	−0.0032 (17)	0.0037 (17)	−0.0023 (15)
O2	0.051 (2)	0.0374 (18)	0.101 (3)	−0.0065 (17)	−0.039 (2)	−0.0001 (19)
C7	0.033 (2)	0.028 (2)	0.036 (2)	−0.0074 (19)	−0.0013 (19)	−0.0014 (16)
C18	0.034 (2)	0.045 (3)	0.029 (2)	−0.001 (2)	0.0042 (18)	0.0009 (18)
C3	0.0254 (19)	0.051 (3)	0.035 (2)	−0.0065 (19)	0.000 (2)	−0.003 (2)
C27	0.037 (2)	0.040 (2)	0.032 (2)	−0.001 (2)	0.000 (2)	−0.0053 (18)
C10	0.028 (2)	0.034 (2)	0.0292 (19)	−0.001 (2)	−0.0037 (17)	−0.0026 (16)
C2	0.042 (3)	0.059 (3)	0.041 (2)	0.007 (3)	−0.006 (2)	0.004 (3)
C14	0.038 (2)	0.050 (3)	0.027 (2)	0.003 (2)	0.0023 (18)	0.003 (2)
C25	0.042 (3)	0.047 (3)	0.031 (2)	0.006 (2)	−0.0071 (19)	−0.008 (2)
C1	0.032 (2)	0.037 (2)	0.045 (2)	0.005 (2)	0.0045 (19)	−0.004 (2)
C15	0.051 (3)	0.060 (3)	0.036 (2)	0.001 (3)	0.007 (2)	0.015 (2)
C26	0.051 (3)	0.039 (3)	0.031 (2)	0.004 (2)	−0.001 (2)	−0.001 (2)
C17	0.033 (2)	0.049 (3)	0.046 (2)	−0.004 (2)	0.0067 (18)	0.003 (2)
C32	0.048 (3)	0.062 (4)	0.057 (3)	−0.008 (3)	0.002 (3)	−0.013 (3)
C31	0.093 (5)	0.068 (4)	0.045 (3)	0.007 (4)	−0.010 (3)	−0.013 (3)
C16	0.053 (3)	0.058 (3)	0.040 (3)	−0.009 (3)	0.014 (2)	0.010 (2)
C24	0.046 (3)	0.058 (3)	0.039 (2)	−0.011 (3)	0.001 (2)	−0.015 (2)
C29	0.044 (3)	0.041 (3)	0.076 (4)	−0.014 (2)	−0.031 (3)	0.014 (3)
C30	0.075 (4)	0.052 (3)	0.059 (3)	−0.004 (3)	0.007 (3)	−0.002 (3)
C35	0.065 (4)	0.065 (4)	0.070 (4)	−0.019 (3)	−0.010 (3)	−0.001 (3)
C33	0.066 (4)	0.066 (4)	0.054 (3)	−0.013 (3)	0.004 (3)	−0.001 (3)
C34	0.057 (4)	0.091 (5)	0.054 (3)	−0.016 (3)	−0.014 (3)	0.004 (3)
C42	0.119 (7)	0.060 (4)	0.056 (4)	0.000 (4)	−0.008 (4)	−0.002 (3)
C38	0.113 (6)	0.057 (4)	0.059 (4)	−0.008 (4)	−0.002 (4)	−0.003 (3)
C39	0.107 (6)	0.081 (5)	0.056 (4)	−0.009 (5)	−0.010 (4)	−0.002 (4)
C41	0.135 (7)	0.054 (4)	0.057 (4)	−0.020 (5)	0.003 (5)	−0.006 (3)
C37	0.110 (6)	0.053 (4)	0.059 (4)	0.001 (4)	−0.011 (4)	−0.003 (3)
C40	0.116 (7)	0.072 (5)	0.064 (4)	−0.018 (5)	0.005 (4)	−0.003 (4)
C36	0.179 (11)	0.097 (7)	0.084 (6)	−0.008 (7)	0.013 (6)	0.030 (5)
C43	0.126 (9)	0.130 (9)	0.083 (5)	0.025 (7)	−0.017 (5)	−0.018 (5)

Geometric parameters (Å, º) top

Ni1—N3	1.843 (3)	C27—H27	0.9299
Ni1—N2	1.853 (3)	C10—H10	0.9299
Ni1—O4	1.868 (3)	C2—C1	1.504 (7)
Ni1—N1	1.942 (3)	C2—H2A	0.9699
O4—C20	1.294 (5)	C2—H2B	0.9700
N3—C12	1.302 (5)	C14—C15	1.390 (7)
N3—C19	1.482 (5)	C14—H14	0.9300
N1—C4	1.498 (5)	C25—C26	1.385 (7)
N1—C1	1.510 (5)	C25—C24	1.388 (8)
N1—C21	1.510 (5)	C25—H25	0.9301
N2—C5	1.388 (5)	C1—H1A	0.9700
N2—C6	1.396 (5)	C1—H1B	0.9700
C12—C11	1.458 (6)	C15—C16	1.383 (8)
C12—C13	1.500 (5)	C15—H15	0.9300
C22—C23	1.389 (6)	C26—H26	0.9301
C22—C27	1.392 (6)	C17—C16	1.381 (7)
C22—C21	1.493 (6)	C17—H17	0.9300
C5—O1	1.213 (5)	C32—C31	1.361 (9)
C5—C4	1.502 (6)	C32—C33	1.395 (8)
C28—C29	1.487 (6)	C32—H32	0.9300
C28—C19	1.530 (5)	C31—C30	1.400 (9)
C28—H28A	0.9699	C31—H31	0.9301
C28—H28B	0.9699	C16—H16	0.9301
O3—C20	1.232 (5)	C24—H24	0.9300
C20—C19	1.508 (6)	C29—H29A	0.9701
C4—C3	1.547 (6)	C29—H29B	0.9700
C4—H4	0.9798	C30—C35	1.374 (9)
C9—C10	1.374 (6)	C30—C36	1.500 (9)
C9—C8	1.395 (6)	C35—C34	1.359 (9)
C9—H9	0.9300	C35—H35	0.9300
C19—H19	0.9800	C33—C34	1.338 (9)
C23—C24	1.383 (7)	C33—H33	0.9301
C23—H23	0.9300	C34—H34	0.9299
C21—H21A	0.9699	C42—C41	1.402 (12)
C21—H21B	0.9700	C42—C37	1.393 (10)
C11—C10	1.405 (6)	C42—H42	0.9301
C11—C6	1.429 (5)	C38—C37	1.369 (10)
C6—C7	1.415 (5)	C38—C39	1.375 (11)
C8—C7	1.375 (6)	C38—H38	0.9300
C8—H8	0.9299	C39—C40	1.378 (10)
C13—C18	1.382 (6)	C39—H39	0.9300
C13—C14	1.399 (6)	C41—C40	1.394 (11)
O2—C29	1.434 (6)	C41—H41	0.9300
O2—H2	0.8199	C37—C43	1.466 (12)
C7—H7	0.9299	C40—H40	0.9300
C18—C17	1.403 (6)	C36—H36A	0.9601
C18—H18	0.9300	C36—H36B	0.9601
C3—C2	1.521 (7)	C36—H36C	0.9600
C3—H3A	0.9700	C43—H43A	0.9599
C3—H3B	0.9701	C43—H43B	0.9601
C27—C26	1.383 (7)	C43—H43C	0.9599

N3—Ni1—N2	94.59 (14)	C9—C10—H10	118.3
N3—Ni1—O4	86.88 (14)	C11—C10—H10	118.6
N2—Ni1—O4	177.89 (15)	C1—C2—C3	104.7 (4)
N3—Ni1—N1	176.16 (15)	C1—C2—H2A	110.8
N2—Ni1—N1	89.15 (14)	C3—C2—H2A	110.6
O4—Ni1—N1	89.41 (14)	C1—C2—H2B	110.7
C20—O4—Ni1	114.7 (3)	C3—C2—H2B	111.2
C12—N3—C19	120.5 (3)	H2A—C2—H2B	108.8
C12—N3—Ni1	128.6 (3)	C15—C14—C13	120.2 (5)
C19—N3—Ni1	110.8 (2)	C15—C14—H14	120.0
C4—N1—C1	104.7 (3)	C13—C14—H14	119.9
C4—N1—C21	112.9 (3)	C26—C25—C24	120.0 (5)
C1—N1—C21	108.5 (3)	C26—C25—H25	119.8
C4—N1—Ni1	106.6 (2)	C24—C25—H25	120.2
C1—N1—Ni1	113.4 (2)	C2—C1—N1	103.2 (4)
C21—N1—Ni1	110.7 (3)	C2—C1—H1A	111.3
C5—N2—C6	121.2 (3)	N1—C1—H1A	111.1
C5—N2—Ni1	111.6 (3)	C2—C1—H1B	111.1
C6—N2—Ni1	127.1 (3)	N1—C1—H1B	110.9
N3—C12—C11	122.4 (4)	H1A—C1—H1B	109.1
N3—C12—C13	119.1 (3)	C16—C15—C14	119.9 (5)
C11—C12—C13	118.5 (3)	C16—C15—H15	120.1
C23—C22—C27	117.4 (4)	C14—C15—H15	120.0
C23—C22—C21	119.7 (4)	C27—C26—C25	119.9 (5)
C27—C22—C21	122.7 (4)	C27—C26—H26	119.9
O1—C5—N2	127.5 (4)	C25—C26—H26	120.3
O1—C5—C4	121.1 (4)	C16—C17—C18	120.3 (5)
N2—C5—C4	111.2 (3)	C16—C17—H17	119.7
C29—C28—C19	114.7 (3)	C18—C17—H17	120.0
C29—C28—H28A	108.8	C31—C32—C33	118.9 (6)
C19—C28—H28A	108.6	C31—C32—H32	120.6
C29—C28—H28B	108.5	C33—C32—H32	120.5
C19—C28—H28B	108.5	C32—C31—C30	121.8 (6)
H28A—C28—H28B	107.5	C32—C31—H31	119.1
O3—C20—O4	124.2 (4)	C30—C31—H31	119.1
O3—C20—C19	120.4 (4)	C15—C16—C17	120.2 (5)
O4—C20—C19	115.4 (3)	C15—C16—H16	119.7
N1—C4—C5	110.1 (3)	C17—C16—H16	120.0
N1—C4—C3	106.0 (3)	C23—C24—C25	119.2 (5)
C5—C4—C3	110.0 (3)	C23—C24—H24	120.2
N1—C4—H4	110.2	C25—C24—H24	120.7
C5—C4—H4	110.3	O2—C29—C28	107.0 (4)
C3—C4—H4	110.1	O2—C29—H29A	110.5
C10—C9—C8	118.2 (4)	C28—C29—H29A	110.5
C10—C9—H9	120.9	O2—C29—H29B	110.2
C8—C9—H9	120.8	C28—C29—H29B	110.2
N3—C19—C20	107.3 (3)	H29A—C29—H29B	108.5
N3—C19—C28	108.8 (3)	C35—C30—C31	117.3 (6)
C20—C19—C28	110.6 (3)	C35—C30—C36	122.8 (7)
N3—C19—H19	109.9	C31—C30—C36	119.8 (7)
C20—C19—H19	110.1	C34—C35—C30	120.2 (6)
C28—C19—H19	110.1	C34—C35—H35	120.2
C24—C23—C22	122.2 (5)	C30—C35—H35	119.6
C24—C23—H23	119.2	C34—C33—C32	119.0 (6)
C22—C23—H23	118.6	C34—C33—H33	120.8
C22—C21—N1	115.0 (3)	C32—C33—H33	120.2
C22—C21—H21A	108.4	C33—C34—C35	122.6 (6)
N1—C21—H21A	108.6	C33—C34—H34	118.6
C22—C21—H21B	108.4	C35—C34—H34	118.7
N1—C21—H21B	108.7	C41—C42—C37	119.5 (7)
H21A—C21—H21B	107.5	C41—C42—H42	120.2
C10—C11—C6	118.5 (4)	C37—C42—H42	120.2
C10—C11—C12	117.6 (4)	C37—C38—C39	121.5 (7)
C6—C11—C12	123.8 (4)	C37—C38—H38	119.0
N2—C6—C7	121.9 (4)	C39—C38—H38	119.6
N2—C6—C11	120.7 (3)	C38—C39—C40	120.6 (8)
C7—C6—C11	117.4 (4)	C38—C39—H39	119.9
C7—C8—C9	120.9 (4)	C40—C39—H39	119.5
C7—C8—H8	119.4	C42—C41—C40	120.3 (7)
C9—C8—H8	119.7	C42—C41—H41	120.0
C18—C13—C14	119.8 (4)	C40—C41—H41	119.7
C18—C13—C12	122.7 (4)	C38—C37—C42	119.1 (8)
C14—C13—C12	117.4 (4)	C38—C37—C43	121.8 (7)
C29—O2—H2	109.1	C42—C37—C43	119.0 (8)
C8—C7—C6	121.9 (4)	C39—C40—C41	118.8 (9)
C8—C7—H7	119.2	C39—C40—H40	120.4
C6—C7—H7	118.9	C41—C40—H40	120.8
C13—C18—C17	119.5 (4)	C30—C36—H36A	109.3
C13—C18—H18	120.2	C30—C36—H36B	109.2
C17—C18—H18	120.3	H36A—C36—H36B	109.5
C2—C3—C4	105.4 (4)	C30—C36—H36C	110.0
C2—C3—H3A	110.9	H36A—C36—H36C	109.5
C4—C3—H3A	110.9	H36B—C36—H36C	109.4
C2—C3—H3B	110.2	C37—C43—H43A	109.0
C4—C3—H3B	110.8	C37—C43—H43B	109.9
H3A—C3—H3B	108.7	H43A—C43—H43B	109.5
C26—C27—C22	121.4 (5)	C37—C43—H43C	109.5
C26—C27—H27	119.4	H43A—C43—H43C	109.5
C22—C27—H27	119.2	H43B—C43—H43C	109.5
C9—C10—C11	123.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.94	2.720 (5)	159

Symmetry code: (i) x+1/2, −y+5/2, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₉H₂₉N₃O₄)]·2C₇H₈
M_r	726.53
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	11.2660 (14), 12.8570 (9), 24.527 (3)
V (Å³)	3552.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.36 × 0.23 × 0.20

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction	Gaussian (Coppens, 1970)
T_min, T_max	0.852, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	21133, 7165, 6170
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.142, 1.01
No. of reflections	7165
No. of parameters	461
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.44
Absolute structure	Flack (1983), 3089 Friedel pairs
Absolute structure parameter	0.000 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.94	2.720 (5)	158.8

Symmetry code: (i) x+1/2, −y+5/2, −z+2.

Acknowledgements

ZP and MN thank the Ministry of Education, Youth and Sports of the Czech Republic for financial support of this work within the framework of research project MSM 0021627501.

References

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