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The title compound, [Ni(C7H5O3)2(C10H24N4)], contains octahedral NiII in a centrosymmetric trans configuration with Ni-N distances of 2.0637 (17) and 2.0699 (16) Å and an Ni-O distance of 2.1100 (14) Å. The mol­ecules are linked by a single type of O-H...O hydrogen bond [O...O 2.618 (2) Å and O-H...O 161°] into two-dimensional sheets; a singletype of N-H...O hydrogen bond [N...O 2.991 (2) Å and N-H...O 139°] links these sheets into a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199014249/sk1344sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199014249/sk1344Isup2.hkl
Contains datablock I

CCDC reference: 142735

Comment top

The tetra-aza macrocycles 1,4,8,11-tetraazacyclotetradecane (cyclam, C10H24N4) and its hexa-C-methyl analogue 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane [tet-a (meso form) and tet-b (racemic) C16H36N4] form adducts with oxygen-containing hydrogen-bond donors which exhibit a wide range of supramolecular architectures (Ferguson et al., 1998, 1999; Gregson et al., 1999; Lough et al., 1999). However, despite the great structural variety exhibited by these adducts, a common feature is the formation by double proton-capture of dications (C10H26N4)2+ and (C16H38N4)2+ in which two protons are held within the N4 cavity by means of N—H···N hydrogen bonds. Associated with this intramolecular constraint is the adoption by the macrocycles of the fairly rigid and nearly-planar trans-III conformation (Barefield, Bianchi et al., 1986).

Both of these macrocycles form nickel(II) complexes in which the coordination of the metal may be either square planar (Prasad & McAuley, 1983; Barefield, Bianchi et al., 1986; Adam et al., 1991) or, in the presence of two additional ligands, octahedral: in the octahedral complexes the two additional ligand sites may be mutually trans, when the trans-III conformation of the macrocyclic ligand is retained (Ito et al., 1984; Mochizuki & Kondo, 1995; Choi et al., 1999) or mutually cis, when the macrocycle is necessarily heavily folded (Whimp et al., 1970; Curtis et al., 1973; Barefield, Bianchi et al., 1986). Entirely similar properties are exhibited by the tetra-C-methyl derivative of cyclam (Hay et al., 1982; Barefield, Freeman & Van Derveer, 1986; Hambley, 1986) confirming that the behaviour of the macrocycle is independent of the degree of C-methyl substitution.

In view of both the configurational versatility of a cation such as [Ni(cyclam)]2+, and the great structural diversity of the metal-free macrocycles in supramolecular chemistry (Ferguson et al., 1998, 1999; Gregson et al., 1999; Lough et al., 1999), it is thus of interest to investigate the behaviour of [Ni(cyclam)]2+ with oxygen-containing hydrogen-bond donors which themselves contain sufficient additional hydrogen-bonding capacity to generate supramolecular aggregates. Anionic ligands L could, in principle, be attached to the Ni(cyclam)]2+ cation either via Ni—L coordinate bonds, or via N—H···L hydrogen bonds, or by some combination of the two, thus affording the possibility of either square-planar or octahedral Ni(II). Here we report the structural characterization of one such adduct, [Ni(C10H24N4)]2+.2[(HOC6H4COO)] (I), formed with 4-hydroxybenzoic acid.

In compound (I) the Ni adopts a trans-octahedral configuration (Fig. 1) with 4-hydroxybenzoate anions acting as the axial ligands. The molecules lie across centres of inversion in P21/n giving a pseudo-I arrangement of Ni atoms. The axial 4-hydroxybenzoate ligands bind to the metal in only monodentate fashion, although they are also connected to the cyclam ligand by means of N—H···O hydrogen bonds (Fig.1 and Table 2), so generating a novel S(6) synthon (Bernstein et al., 1995; Desiraju 1995). By contrast in the salt formed between the trans-[Ni(cyclam)(H2O)2]2+ cation and the tri-anion of benzene-1,3,5-tricarboxylic acid, the cations and anions are linked solely by O—H···O hydrogen bonds in which water ligands act as hydrogen-bond donors (Choi et al., 1999). It is noteworthy that in both the cations [Ni(tet-b)OCOCH3]+ (Whimp et al., 1970) and [Ni(tet-a)(acac)]+ (Curtis, 1973) [(acac) = (CH3COCHCOCH3)] the oxygen ligands are each bound to Ni in a bidentate fashion, so that the two O sites are mutually cis, and the macrocycle is folded: indeed the [Ni(tet-a)(acac)]+ cations lie on twofold rotation axes. On the other hand, when H2O molecules act as the additional ligands, both cis (folded) and trans (planar) configurations of the cation [Ni(cyclam)(H2O)2]2+ can be observed (Barefield, Bianchi et al., 1986; Mochizuki & Kondo, 1995; Choi et al., 1999).

The Ni—N distances in (I) (Table 1) are typical of those observed in octahedral NiII complexes of cyclam and its C-methyl derivatives (Whimp et al., 1970; Curtis et al., 1973; Hay et al., 1982; Ito et al., 1984; Barefield, Bianchi et al., 1986; Barefield, Freeman & Van Derveer, 1986; Hambley, 1986; Mochizuki & Kondo, 1995; Choi et al., 1999), but significantly shorter than those observed in the square-planar systems (Prasad & McAuley, 1983; Barefield, Bianchi et al., 1986; Adam et al., 1991). The unique Ni—O distance in (I) is a little shorter than those observed in [Ni(cyclam)(H2O)2]2+ cations. In the chloride salt of the cis isomer the values are 2.130 (2) and 2.140 (1) Å (Barefield, Bianchi et al., 1986), and for the centrosymmetric trans isomer the unique Ni—O distance is 2.176 (2) Å in the chloride salt (Mochizuki & Kondo, 1995) and 2.160 (3) Å in the benzene-1,3,5-tricarboxylate salt (Choi et al., 1999). The shorter bond in (I) possibly arises from the anionic nature of the axial ligand; this is supported by the Ni—O distances in the acetato complex [Ni(tet-b)OCOCH3]+, 2.103 (9) and 2.116 (9) Å (Whimp et al., 1970).

Within the macrocyclic ligand the torsional angles (Table 1) indicate almost perfect staggering about all the C—C and C—N bonds, as expected for the trans-III conformation (Barefield, Bianchi et al., 1986); as usual in this conformation, there are four axial N—H bonds which are almost normal to the mean plane of the macrocycle, two on each face. One symmetry-related pair of these bonds is engaged in forming intramolecular N—H···O hydrogen bonds; the other pair form intermolecular N—H···O hydrogen bonds. In the anion the carboxylate group is twisted out of the plane of the aryl ring by 8.2 (2)°.

A combination of O—H···O and N—H···O hydrogen bonds (Table 2) links the neutral molecules (Fig. 1) into a continuous three-dimensional framework. It simplifies considerably the structural description if the effects of the O—H···O and N—H···O hydrogen bonds are treated separately. A single type of intermolecular O—H···O hydrogen bond serves to link the molecules into two-dimensional nets lying parallel to the (101) plane (Fig. 2) and built from a single type of centrosymmetric R44(40) ring. The hydroxyl O14 at (x,y,z) acts as donor to the carboxylate O12 at (0.5 + x,1.5 − y,0.5 + z), so producing a C(8) chain parallel to the [101] direction and generated by the glide plane; the action of the centres of inversion upon these chains generates the two-dimensional net. The molecule centred at (1/2,0.5, 1/2) is a donor of O—H···O hydrogen bonds to the pair of molecules centred at (0,0,0) and (1,1,1), and an acceptor of O—H···O hydrogen bonds from the molecules centred at (0,1,0) and (1,0,1). Just one net of this type is sufficient to account for all the unit-cell contents.

The continuous stack of parallel nets is linked into a three-dimensional framework by chains running parallel to the [100] direction: N4 at (x,y,z) acts as donor to the hydroxylic O14 at (−1 + x,y,z) and propagation of this interaction by the space group generates a C(10)[R22(20)] chain-of-rings (Bernstein et al., 1995), where the rings are centred at (n, 1/2,0.5) (n = zero or integer) (Fig. 3). Thus just two types of intermolecular hydrogen bond serve to link all the molecules into a single supramolecular aggregate. Although the aryl ring planes of the 4-hydroxybenzoate ligands in neighbouring molecules are separated by only ca 3.59 Å, the centroid offset effectively precludes the occurrence of any aromatic π···π stacking interactions between these rings.

The orange-brown colour of (I) is that commonly associated with diamagnetic square-planar NiII, although in (I) the coordination of the Ni is metrically octahedral. The Angular Overlap Model (Burdett, 1980) readily shows that spin-pairing in metrically octahedral d8 complexes of type trans-MX4Y2 is possible, provided only that the ligand-field characteristics of the equatorial and axial ligand X and Y are sufficiently different.

Experimental top

Stoichiometric quantities of [Ni(cyclam)](ClO4)2 and the sodium salt of 4-hydroxybenzoic acid were separately dissolved in water: the solutions were mixed and set aside to crystallize, producing orange-brown crystals of compound (I). Analysis: found C 54.0, H 6.2, N 10.4%. C24H34N4NiO6 requires C 54.0, H 6.4, N 10.5%. Crystals suitable for single-crystal X-ray diffraction were selected directly from the analytical sample.

Refinement top

Compound (I) crystallized in the monoclinic system; space group P21/n from the systematic absences. All H atoms were clearly resolved in difference maps and were treated as riding atoms in the refinement with C—H 0.95 and 0.99 Å, N—H 0.93 Å, O—H 0.84 Å.

Computing details top

Data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: Patterson heavy-atom method and SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEP (Johnson, 1976) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I) showing the formation of a (101) sheet built from R44(40) rings.
[Figure 3] Fig. 3. Part of the crystal structure showing the C(10)[R22(20)] chain-of-rings parallel to the [100] direction.
Bis(4-hydroxybenzoato)(1,4,8,11-tetraazacyclotetradecane)nickel(II) top
Crystal data top
[Ni(C10H24N4)(C7H5O3)2]F(000) = 564
Mr = 533.26Dx = 1.488 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.8397 (6) ÅCell parameters from 2696 reflections
b = 8.7317 (6) Åθ = 2.8–27.6°
c = 12.8670 (9) ŵ = 0.86 mm1
β = 102.160 (4)°T = 100 K
V = 1190.52 (13) Å3Plate, orange-brown
Z = 20.40 × 0.35 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
2696 independent reflections
Radiation source: fine-focus sealed X-ray tube2124 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ scans and ω scans with κ offsetsθmax = 27.6°, θmin = 2.8°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 014
Tmin = 0.724, Tmax = 0.919k = 011
19420 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: heavy-atom
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0304P)2 + 0.7434P]
where P = (Fo2 + 2Fc2)/3
2696 reflections(Δ/σ)max < 0.001
161 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
[Ni(C10H24N4)(C7H5O3)2]V = 1190.52 (13) Å3
Mr = 533.26Z = 2
Monoclinic, P21/nMo Kα radiation
a = 10.8397 (6) ŵ = 0.86 mm1
b = 8.7317 (6) ÅT = 100 K
c = 12.8670 (9) Å0.40 × 0.35 × 0.10 mm
β = 102.160 (4)°
Data collection top
Kappa-CCD
diffractometer
2696 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
2124 reflections with I > 2σ(I)
Tmin = 0.724, Tmax = 0.919Rint = 0.040
19420 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.089H-atom parameters constrained
S = 1.03Δρmax = 0.41 e Å3
2696 reflectionsΔρmin = 0.41 e Å3
161 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

− 5.1812(0.0043) x + 5.8785(0.0055) y + 8.3917(0.0080) z = 3.7953(0.0054)

* −0.0343 (0.0018) C11 * −0.0531 (0.0016) C12 * −0.0354 (0.0016) C13 * 0.0097 (0.0018) C14 * −0.0385 (0.0016) C15 * −0.0529 (0.0016) C16 * 0.1145 (0.0014) C17 * 0.0902 (0.0013) O14 0.2953 (0.0023) O11 0.0992 (0.0025) O12

Rms deviation of fitted atoms = 0.0621

− 3.8918 (0.0108) x + 6.5520 (0.0056) y + 7.9543 (0.0103) z = 5.1250 (0.0103)

Angle to previous plane (with approximate e.s.d.) = 8.2 (2)

* 0.0036 (0.0005) C11 * −0.0130 (0.0016) C17 * 0.0046 (0.0006) O11 * 0.0047 (0.0006) O12

Rms deviation of fitted atoms = 0.0075

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.01358 (12)
O110.69322 (13)0.55693 (17)0.52532 (11)0.0177 (3)
O120.71509 (13)0.72392 (18)0.39848 (12)0.0247 (4)
O141.25704 (13)0.7615 (2)0.70565 (11)0.0235 (4)
C110.89460 (18)0.6652 (2)0.53451 (15)0.0155 (4)
C120.94674 (19)0.5795 (2)0.62455 (16)0.0175 (4)
C131.06822 (19)0.6078 (3)0.68179 (16)0.0193 (5)
C141.13882 (19)0.7244 (3)0.64910 (16)0.0187 (5)
C151.09080 (19)0.8056 (3)0.55679 (17)0.0193 (5)
C160.96924 (19)0.7766 (2)0.50040 (16)0.0181 (5)
C170.75808 (19)0.6463 (2)0.48120 (15)0.0162 (4)
N10.44850 (15)0.6529 (2)0.37550 (13)0.0164 (4)
C20.3843 (2)0.7805 (2)0.41727 (17)0.0208 (5)
C30.4560 (2)0.8179 (2)0.52957 (17)0.0208 (5)
N40.46405 (16)0.6781 (2)0.59485 (13)0.0162 (4)
C50.5508 (2)0.6932 (3)0.69956 (16)0.0207 (5)
C60.5559 (2)0.5456 (3)0.76362 (16)0.0214 (5)
C70.62396 (19)0.4118 (3)0.72507 (16)0.0198 (5)
H141.25860.75460.77100.035*
H120.89830.50030.64710.021*
H131.10280.54820.74270.023*
H151.14110.88110.53230.023*
H160.93640.83330.43770.022*
H10.52280.69230.36100.020*
H2A0.29630.75120.41850.025*
H2B0.38190.87140.37100.025*
H3A0.54180.85500.52770.025*
H3B0.41150.89950.56060.025*
H40.38400.66130.60790.019*
H5A0.52220.77820.73960.025*
H5B0.63650.71840.68920.025*
H6A0.59760.56800.83820.026*
H6B0.46830.51350.76360.026*
H7A0.70730.44670.71440.024*
H7B0.63840.33090.78020.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01193 (19)0.01370 (19)0.0147 (2)0.00039 (16)0.00177 (14)0.00004 (16)
O110.0128 (7)0.0200 (8)0.0196 (7)0.0027 (6)0.0018 (6)0.0028 (6)
O120.0159 (7)0.0353 (10)0.0217 (8)0.0024 (7)0.0010 (6)0.0104 (7)
O140.0121 (7)0.0387 (10)0.0188 (7)0.0037 (7)0.0012 (6)0.0044 (7)
C110.0137 (10)0.0168 (11)0.0156 (10)0.0012 (8)0.0022 (8)0.0022 (8)
C120.0159 (10)0.0167 (11)0.0204 (10)0.0009 (9)0.0051 (9)0.0009 (9)
C130.0190 (10)0.0206 (11)0.0175 (10)0.0044 (9)0.0022 (9)0.0018 (9)
C140.0131 (10)0.0230 (12)0.0193 (10)0.0002 (9)0.0019 (9)0.0057 (9)
C150.0172 (11)0.0212 (11)0.0216 (11)0.0052 (9)0.0089 (9)0.0028 (9)
C160.0180 (11)0.0206 (11)0.0158 (10)0.0013 (9)0.0033 (9)0.0002 (9)
C170.0151 (10)0.0184 (11)0.0155 (10)0.0003 (9)0.0040 (8)0.0035 (9)
N10.0131 (8)0.0175 (9)0.0182 (9)0.0001 (7)0.0025 (7)0.0002 (8)
C20.0177 (10)0.0185 (11)0.0266 (11)0.0038 (9)0.0054 (9)0.0048 (10)
C30.0235 (11)0.0143 (11)0.0256 (11)0.0015 (9)0.0075 (10)0.0016 (9)
N40.0144 (8)0.0154 (9)0.0190 (9)0.0022 (7)0.0044 (7)0.0005 (7)
C50.0215 (11)0.0221 (12)0.0182 (10)0.0036 (9)0.0033 (9)0.0058 (9)
C60.0191 (11)0.0288 (12)0.0153 (10)0.0046 (9)0.0013 (9)0.0008 (9)
C70.0147 (10)0.0242 (12)0.0186 (10)0.0032 (9)0.0007 (9)0.0044 (9)
Geometric parameters (Å, º) top
Ni1—N12.0699 (16)C12—C131.389 (3)
Ni1—N1i2.0699 (16)C13—C141.391 (3)
Ni1—N42.0637 (17)C14—C151.387 (3)
Ni1—N4i2.0637 (17)C15—C161.387 (3)
Ni1—O11i2.1100 (14)N1—C21.474 (3)
Ni1—O112.1100 (14)N1—C7i1.478 (3)
O11—C171.263 (2)C2—C31.525 (3)
O12—C171.265 (2)C3—N41.474 (3)
O14—C141.373 (2)N4—C51.478 (3)
C11—C121.395 (3)C5—C61.524 (3)
C11—C161.393 (3)C6—C71.520 (3)
C11—C171.503 (3)C7—N1i1.478 (3)
N4—Ni1—N4i180.0C12—C13—C14119.39 (19)
N1—Ni1—N485.29 (7)O14—C14—C13121.63 (19)
N4i—Ni1—N194.71 (7)O14—C14—C15118.23 (19)
N4—Ni1—N1i94.71 (7)C13—C14—C15120.14 (19)
N4i—Ni1—N1i85.29 (7)C14—C15—C16119.9 (2)
N1—Ni1—N1i180.0C11—C16—C15120.90 (19)
N4—Ni1—O11i87.93 (6)O11—C17—O12124.62 (18)
N4i—Ni1—O11i92.07 (6)O11—C17—C11116.78 (18)
N1—Ni1—O11i86.29 (6)O12—C17—C11118.54 (18)
N1i—Ni1—O11i93.71 (6)C7i—N1—C2113.82 (16)
N4—Ni1—O1192.07 (6)C2—N1—Ni1106.04 (12)
N4i—Ni1—O1187.93 (6)C7i—N1—Ni1115.96 (13)
N1—Ni1—O1193.71 (6)N1—C2—C3108.76 (17)
N1i—Ni1—O1186.29 (6)C2—C3—N4108.61 (17)
O11i—Ni1—O11180.0C3—N4—C5113.27 (16)
C17—O11—Ni1134.82 (13)C3—N4—Ni1106.44 (12)
C12—C11—C16118.39 (18)C5—N4—Ni1116.33 (13)
C16—C11—C17120.93 (18)N4—C5—C6111.15 (17)
C12—C11—C17120.50 (18)C5—C6—C7115.98 (18)
C11—C12—C13121.2 (2)C6—C7—N1i112.03 (17)
C16—C11—C12—C132.6 (3)C12—C11—C17—O113.9 (3)
C17—C11—C12—C13172.54 (19)C16—C11—C17—O126.4 (3)
C11—C12—C13—C140.4 (3)C12—C11—C17—O12178.56 (19)
C12—C13—C14—O14176.99 (19)C7i—N1—C2—C3169.9 (2)
C12—C13—C14—C153.6 (3)N1—C2—C3—N456.4 (2)
O14—C14—C15—C16176.80 (19)C2—C3—N4—C5169.7 (2)
C13—C14—C15—C163.8 (3)C3—N4—C5—C6179.9 (2)
C14—C15—C16—C110.7 (3)N4—C5—C6—C771.6 (2)
C12—C11—C16—C152.4 (3)C5—C6—C7—N1i71.4 (2)
C17—C11—C16—C15172.68 (19)C6—C7—N1i—C2i178.5 (2)
C16—C11—C17—O11171.11 (18)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O120.932.062.909 (2)152
N4—H4···O14ii0.932.232.991 (2)139
O14—H14···O12iii0.841.812.618 (2)161
C7—H7A···O110.992.593.096 (3)112
Symmetry codes: (ii) x1, y, z; (iii) x+1/2, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Ni(C10H24N4)(C7H5O3)2]
Mr533.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)10.8397 (6), 8.7317 (6), 12.8670 (9)
β (°) 102.160 (4)
V3)1190.52 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.86
Crystal size (mm)0.40 × 0.35 × 0.10
Data collection
DiffractometerKappa-CCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.724, 0.919
No. of measured, independent and
observed [I > 2σ(I)] reflections
19420, 2696, 2124
Rint0.040
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.089, 1.03
No. of reflections2696
No. of parameters161
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.41

Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, Patterson heavy-atom method and SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1976) and PLATON (Spek, 1999), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
Ni1—N12.0699 (16)N1—C21.474 (3)
Ni1—N42.0637 (17)C2—C31.525 (3)
Ni1—O112.1100 (14)C3—N41.474 (3)
O11—C171.263 (2)N4—C51.478 (3)
O12—C171.265 (2)C5—C61.524 (3)
O14—C141.373 (2)C6—C71.520 (3)
C11—C171.503 (3)C7—N1i1.478 (3)
N1—Ni1—N485.29 (7)C7i—N1—C2113.82 (16)
N1—Ni1—O11i86.29 (6)N1—C2—C3108.76 (17)
N4—Ni1—O1192.07 (6)C2—C3—N4108.61 (17)
O14—C14—C13121.63 (19)C3—N4—C5113.27 (16)
O14—C14—C15118.23 (19)N4—C5—C6111.15 (17)
O11—C17—O12124.62 (18)C5—C6—C7115.98 (18)
O11—C17—C11116.78 (18)C6—C7—N1i112.03 (17)
O12—C17—C11118.54 (18)
C7i—N1—C2—C3169.9 (2)N4—C5—C6—C771.6 (2)
N1—C2—C3—N456.4 (2)C5—C6—C7—N1i71.4 (2)
C2—C3—N4—C5169.7 (2)C6—C7—N1i—C2i178.5 (2)
C3—N4—C5—C6179.9 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O120.932.062.909 (2)152
N4—H4···O14ii0.932.232.991 (2)139
O14—H14···O12iii0.841.812.618 (2)161
Symmetry codes: (ii) x1, y, z; (iii) x+1/2, y+3/2, z+1/2.
 

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