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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): m1588.
Published online 2008 November 22. doi:  10.1107/S1600536808038051
PMCID: PMC2960142

(Benzoato-κ2 O,O′)(5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­azacyclo­tetra­decane-κ4 N,N′,N′′,N′′′)nickel(II) perchlorate benzoic acid solvate

Abstract

In the title compound, [Ni(C7H5O2)(C16H36N4)]ClO4·C7H6O2, the Ni atom displays a distorted octa­hedral coordination geometry with four N atoms of the ligand rac-5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­azacyclo­tetra­decane (L) in a folded configuration and two benzoate (bz) O atoms. The [Ni(rac-L)(bz)]+ complex cation, perchlorate anion and benzoic acid mol­ecules engage in hydrogen bonding, with N(...)O distances between 2.970 (3) and 3.123 (3) Å and an O(...)O distance of 2.691 (3) Å.

Related literature

For related background, see: Tait & Busch (1976 [triangle]); Curtis (1965 [triangle]). For related structures, see: Ou et al. (2008 [triangle]); Basiuk et al. (2001 [triangle]); Jiang et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1588-scheme1.jpg

Experimental

Crystal data

  • [Ni(C7H5O2)(C16H36N4)]ClO4·C7H6O2
  • M r = 685.88
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1588-efi1.jpg
  • a = 8.8035 (11) Å
  • b = 18.138 (2) Å
  • c = 20.966 (3) Å
  • β = 95.512 (2)°
  • V = 3332.4 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.72 mm−1
  • T = 293 (2) K
  • 0.48 × 0.26 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.725, T max = 0.900
  • 22312 measured reflections
  • 7304 independent reflections
  • 5272 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.126
  • S = 1.11
  • 7304 reflections
  • 404 parameters
  • H-atom parameters constrained
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038051/pv2117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038051/pv2117Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Key Subject Construction Project of Hunan Province (grant No. 2006-180), the Scientific Research Project of the Hunan Provincial Finance Bureau and Education Department (grant No. 08C366), and the Foundation for University Key Teachers of the Education Department of Hunan Province for supporting this study.

supplementary crystallographic information

Comment

It is important to control the geometries of ML2+ [M = Ni(II), Co(II), Cu(II)] with cis- or trans-conformation, since they form different structures and show different properties (Tait & Busch, 1976; Curtis, 1965). Continuing our research (Ou et al., 2008), we have synthesized the title compound, (I), which is presented in this paper.

The asymmetric unit of the title compouind, (I), contains one [Ni(rac-L)(bz)]+ cation, one [ClO4]- anion and one benzoic acid molecule (Fig. 1). The six-coordinated Ni2+ of the complex [Ni(rac-L)(bz)]+ cation displays a distorted octahedral geometry by coordination with four nitrogen atoms of the macrocyclic ligand L in a folded configuration, and two carboxylate oxygen atoms of benzoic acid in cis-position. The Ni—N distances range between 2.082 (2) to 2.134 (2) Å, and are slightly shorter than the Ni—O distance (2.116 (2) and 2.212 (2) Å). The neighbouring cations, anions and benzoic acid are connected to each other through intermolecular hydrogen bond of the types N—H···O and O—H···O (Table 1, Fig. 2). The crystal structures of a few compound closely related to (I) have been reported (Ou et al., 2008a,b; Basiuk et al. 2001; Jiang et al., 2005).

Experimental

Benzoic acid (0.36 g, 3 mmol) and NaOH (0.08 g, 2 mmol) were dissolved in 15 ml of water. To this solution was added [Ni(rac-L)](ClO4)2 (0.54 g, 1 mmol) dissolved in 2 ml of CH3CN. The solution was left to stand at room temperature and blue crystals formed after several weeks.

Refinement

H atoms bound to C, O and N atoms were positioned geometrically and refined using the riding model, and with C—H = 0.93, 0.96, 0.97 and 0.98 Å, for aryl, methyl, methylene and methine H-atoms, O—H = 0.82 Å and N—H = 0.91 Å, and with Uiso(H) set to 1.5Ueq(methyl C) and 1.2Ueq(the rest of the parent atoms).

Figures

Fig. 1.
The molecular structure of (I), showing displacement ellipsoids at the 30% probability level; H-atoms have been excluded for clarity.
Fig. 2.
A view of the packing of the title compound along a axis.

Crystal data

[Ni(C7H5O2)(C16H36N4)]ClO4·C7H6O2F000 = 1456
Mr = 685.88Dx = 1.367 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
a = 8.8035 (11) ÅCell parameters from 7647 reflections
b = 18.138 (2) Åθ = 2.3–26.9º
c = 20.966 (3) ŵ = 0.72 mm1
β = 95.512 (2)ºT = 293 (2) K
V = 3332.4 (7) Å3Prism, light-blue
Z = 40.48 × 0.26 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer7304 independent reflections
Radiation source: fine-focus sealed tube5272 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 293(2) Kθmax = 27.1º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→11
Tmin = 0.725, Tmax = 0.900k = −20→23
22312 measured reflectionsl = −26→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.126  w = 1/[σ2(Fo2) + (0.0643P)2 + 0.7856P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
7304 reflectionsΔρmax = 0.58 e Å3
404 parametersΔρmin = −0.42 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.
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 > σ(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)

xyzUiso*/Ueq
Ni10.64844 (4)0.771339 (17)0.564296 (14)0.01920 (11)
Cl10.08075 (7)0.70176 (4)0.44238 (3)0.02611 (16)
N30.5075 (2)0.77519 (11)0.47565 (9)0.0208 (5)
H3C0.40980.77160.48610.025*
N10.8063 (2)0.76085 (12)0.64759 (9)0.0219 (5)
H1C0.78380.79830.67400.026*
O10.5623 (2)0.87209 (10)0.60812 (8)0.0226 (4)
O20.4528 (2)0.76422 (10)0.61520 (8)0.0253 (4)
N40.6736 (2)0.65959 (12)0.54328 (10)0.0220 (5)
H4D0.76380.65400.52600.026*
O6−0.0503 (3)0.67518 (13)0.47084 (12)0.0527 (6)
O50.1734 (3)0.64124 (12)0.42671 (10)0.0428 (6)
N20.8262 (2)0.82271 (12)0.52275 (10)0.0233 (5)
H2C0.87280.78760.50050.028*
O80.1626 (3)0.74917 (15)0.48804 (11)0.0530 (6)
C60.5101 (3)0.84150 (15)0.43238 (12)0.0258 (6)
C140.8130 (3)0.69224 (14)0.68843 (12)0.0244 (6)
C90.5394 (3)0.70458 (14)0.44370 (12)0.0257 (6)
H9A0.63510.70810.42450.031*
H9B0.45890.69430.41000.031*
C180.3568 (3)0.86310 (14)0.67420 (11)0.0229 (6)
C170.4615 (3)0.83124 (14)0.62995 (11)0.0217 (5)
O70.0320 (4)0.74181 (15)0.38604 (11)0.0672 (8)
C70.4224 (3)0.82719 (17)0.36663 (12)0.0326 (7)
H7A0.47330.78940.34470.049*
H7B0.41870.87170.34180.049*
H7C0.32040.81150.37240.049*
C30.7870 (3)0.88481 (15)0.47783 (12)0.0278 (6)
H3A0.73780.92350.50110.033*
C50.6758 (3)0.86021 (15)0.42156 (12)0.0268 (6)
H5A0.71930.81700.40300.032*
H5B0.67270.89890.38950.032*
C230.3032 (4)0.93478 (16)0.66577 (14)0.0359 (7)
H230.33290.96340.63230.043*
C150.6751 (3)0.69292 (16)0.72747 (13)0.0317 (7)
H15A0.67860.73620.75400.048*
H15B0.67700.64970.75400.048*
H15C0.58300.69330.69890.048*
C100.5483 (3)0.64341 (15)0.49227 (12)0.0265 (6)
H10A0.45210.63930.51100.032*
H10B0.56790.59690.47170.032*
C10.9551 (3)0.78073 (16)0.62444 (13)0.0289 (6)
H1A0.99630.73850.60350.035*
H1B1.02690.79440.66050.035*
C20.9351 (3)0.84413 (16)0.57805 (12)0.0286 (6)
H2A0.89650.88680.59920.034*
H2B1.03270.85710.56320.034*
C130.8127 (3)0.62333 (15)0.64645 (12)0.0280 (6)
H13A0.90160.62570.62250.034*
H13B0.82610.58090.67460.034*
C80.4328 (4)0.90494 (16)0.46373 (13)0.0334 (7)
H8A0.32760.89290.46690.050*
H8B0.43900.94860.43830.050*
H8C0.48300.91340.50580.050*
C190.3146 (3)0.82170 (16)0.72532 (12)0.0298 (6)
H190.34950.77350.73110.036*
C40.9287 (4)0.91798 (16)0.45124 (14)0.0373 (7)
H4A1.00070.93290.48610.056*
H4B0.89920.96000.42510.056*
H4C0.97470.88170.42580.056*
C160.9575 (3)0.69124 (16)0.73619 (13)0.0346 (7)
H16A1.04630.68810.71310.052*
H16B0.95430.64930.76400.052*
H16C0.96190.73560.76130.052*
C110.6742 (3)0.60875 (14)0.59886 (12)0.0260 (6)
H110.58260.61890.62050.031*
C120.6712 (4)0.52789 (16)0.58023 (15)0.0436 (8)
H12A0.58210.51810.55130.065*
H12B0.66850.49810.61790.065*
H12C0.76100.51630.55960.065*
C200.2205 (3)0.85191 (18)0.76787 (13)0.0365 (7)
H200.19380.82440.80250.044*
C220.2050 (4)0.96368 (19)0.70754 (15)0.0443 (8)
H220.16511.01080.70080.053*
C210.1668 (4)0.92287 (19)0.75872 (15)0.0423 (8)
H210.10430.94320.78740.051*
O30.3369 (3)0.47611 (10)0.80658 (9)0.0360 (5)
H3B0.37300.44650.83340.054*
O40.2469 (3)0.37507 (12)0.75552 (10)0.0530 (7)
C300.2927 (3)0.55960 (15)0.69518 (13)0.0303 (6)
H300.33930.58190.73190.036*
C290.2669 (3)0.59937 (16)0.63842 (14)0.0342 (7)
H290.29660.64850.63700.041*
C240.2768 (3)0.44005 (16)0.75521 (13)0.0308 (6)
C250.2481 (3)0.48619 (15)0.69640 (12)0.0264 (6)
C260.1793 (3)0.45290 (16)0.64188 (13)0.0320 (7)
H260.15090.40360.64290.038*
C270.1524 (4)0.49276 (18)0.58565 (13)0.0362 (7)
H270.10460.47060.54910.043*
C280.1971 (4)0.56580 (17)0.58414 (14)0.0365 (7)
H280.18010.59250.54630.044*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.02147 (19)0.01929 (18)0.01704 (16)−0.00093 (13)0.00287 (12)−0.00228 (13)
Cl10.0256 (4)0.0316 (4)0.0216 (3)0.0031 (3)0.0049 (3)0.0003 (3)
N30.0188 (11)0.0249 (12)0.0193 (10)−0.0003 (9)0.0048 (8)0.0003 (9)
N10.0241 (12)0.0218 (12)0.0198 (10)0.0002 (9)0.0028 (9)−0.0028 (9)
O10.0251 (10)0.0244 (10)0.0187 (8)−0.0022 (8)0.0044 (7)−0.0002 (7)
O20.0289 (11)0.0240 (10)0.0233 (9)−0.0022 (8)0.0044 (8)−0.0030 (8)
N40.0210 (12)0.0240 (12)0.0214 (10)−0.0026 (9)0.0035 (9)−0.0034 (9)
O60.0437 (14)0.0526 (15)0.0674 (16)−0.0160 (11)0.0336 (12)−0.0186 (12)
O50.0486 (14)0.0445 (13)0.0372 (11)0.0199 (11)0.0146 (10)0.0008 (10)
N20.0251 (12)0.0221 (12)0.0231 (11)−0.0010 (9)0.0038 (9)−0.0029 (9)
O80.0355 (14)0.0714 (17)0.0527 (14)−0.0149 (12)0.0072 (11)−0.0293 (12)
C60.0291 (15)0.0268 (15)0.0212 (12)−0.0008 (11)0.0008 (11)0.0031 (11)
C140.0281 (15)0.0251 (14)0.0199 (12)0.0029 (11)0.0015 (11)0.0002 (11)
C90.0325 (16)0.0257 (14)0.0185 (12)−0.0047 (12)−0.0003 (11)−0.0047 (10)
C180.0221 (14)0.0271 (14)0.0195 (12)−0.0008 (11)0.0013 (10)−0.0017 (10)
C170.0244 (14)0.0240 (14)0.0157 (11)0.0014 (11)−0.0024 (10)0.0012 (10)
O70.107 (2)0.0608 (17)0.0328 (12)0.0366 (16)−0.0002 (14)0.0145 (12)
C70.0348 (17)0.0392 (17)0.0230 (13)−0.0028 (13)−0.0018 (12)0.0060 (12)
C30.0344 (16)0.0204 (14)0.0288 (14)−0.0024 (12)0.0044 (12)−0.0001 (11)
C50.0337 (16)0.0236 (14)0.0234 (13)−0.0027 (12)0.0049 (11)0.0051 (11)
C230.0443 (19)0.0305 (17)0.0345 (15)0.0063 (14)0.0118 (14)−0.0006 (13)
C150.0438 (18)0.0303 (16)0.0222 (13)0.0037 (13)0.0090 (12)0.0011 (12)
C100.0269 (15)0.0271 (15)0.0247 (13)−0.0062 (11)−0.0011 (11)−0.0037 (11)
C10.0210 (14)0.0395 (17)0.0258 (13)−0.0041 (12)0.0006 (11)0.0002 (12)
C20.0248 (15)0.0353 (16)0.0251 (13)−0.0086 (12)0.0001 (11)−0.0050 (12)
C130.0324 (16)0.0252 (15)0.0261 (13)0.0028 (12)0.0016 (11)−0.0012 (11)
C80.0375 (18)0.0328 (16)0.0293 (14)0.0075 (13)0.0000 (12)0.0042 (12)
C190.0336 (17)0.0337 (16)0.0222 (13)−0.0015 (13)0.0037 (12)−0.0006 (12)
C40.0380 (18)0.0305 (17)0.0433 (17)−0.0106 (13)0.0030 (14)0.0065 (14)
C160.0395 (18)0.0364 (17)0.0259 (14)0.0026 (14)−0.0071 (12)−0.0011 (12)
C110.0326 (16)0.0211 (14)0.0246 (13)−0.0028 (11)0.0040 (11)0.0009 (11)
C120.069 (2)0.0228 (16)0.0367 (16)−0.0051 (15)−0.0085 (16)0.0017 (13)
C200.0347 (17)0.050 (2)0.0263 (14)−0.0108 (14)0.0100 (12)−0.0080 (13)
C220.045 (2)0.0380 (19)0.0514 (19)0.0114 (15)0.0147 (16)−0.0105 (15)
C210.0358 (18)0.056 (2)0.0379 (17)−0.0041 (16)0.0158 (14)−0.0217 (15)
O30.0535 (14)0.0279 (11)0.0243 (10)0.0026 (10)−0.0078 (9)0.0011 (8)
O40.093 (2)0.0331 (13)0.0289 (11)−0.0227 (12)−0.0128 (12)0.0130 (9)
C300.0327 (16)0.0280 (15)0.0297 (14)−0.0047 (12)0.0005 (12)0.0028 (12)
C290.0327 (17)0.0253 (15)0.0455 (17)0.0006 (12)0.0085 (13)0.0099 (13)
C240.0365 (17)0.0299 (16)0.0255 (14)−0.0018 (13)0.0010 (12)0.0037 (12)
C250.0286 (16)0.0257 (15)0.0250 (13)−0.0016 (11)0.0028 (11)0.0038 (11)
C260.0370 (18)0.0307 (16)0.0283 (14)−0.0033 (13)0.0032 (12)0.0034 (12)
C270.0414 (19)0.0423 (18)0.0244 (13)−0.0005 (14)0.0005 (12)0.0038 (13)
C280.0374 (18)0.0431 (19)0.0297 (15)0.0064 (14)0.0068 (13)0.0152 (13)

Geometric parameters (Å, °)

Ni1—N22.082 (2)C15—H15C0.9600
Ni1—N42.091 (2)C10—H10A0.9700
Ni1—O22.116 (2)C10—H10B0.9700
Ni1—N12.133 (2)C1—C21.506 (4)
Ni1—N32.134 (2)C1—H1A0.9700
Ni1—O12.212 (2)C1—H1B0.9700
Cl1—O71.418 (2)C2—H2A0.9700
Cl1—O51.425 (2)C2—H2B0.9700
Cl1—O81.429 (2)C13—C111.523 (4)
Cl1—O61.433 (2)C13—H13A0.9700
N3—C91.484 (3)C13—H13B0.9700
N3—C61.508 (3)C8—H8A0.9600
N3—H3C0.9100C8—H8B0.9600
N1—C11.485 (3)C8—H8C0.9600
N1—C141.508 (3)C19—C201.387 (4)
N1—H1C0.9100C19—H190.9300
O1—C171.274 (3)C4—H4A0.9600
O2—C171.255 (3)C4—H4B0.9600
N4—C111.485 (3)C4—H4C0.9600
N4—C101.490 (3)C16—H16A0.9600
N4—H4D0.9100C16—H16B0.9600
N2—C21.484 (3)C16—H16C0.9600
N2—C31.487 (3)C11—C121.517 (4)
N2—H2C0.9100C11—H110.9800
C6—C81.518 (4)C12—H12A0.9600
C6—C51.536 (4)C12—H12B0.9600
C6—C71.536 (3)C12—H12C0.9600
C14—C131.529 (4)C20—C211.378 (5)
C14—C151.529 (4)C20—H200.9300
C14—C161.541 (4)C22—C211.372 (5)
C9—C101.503 (4)C22—H220.9300
C9—H9A0.9700C21—H210.9300
C9—H9B0.9700O3—C241.326 (3)
C18—C191.388 (4)O3—H3B0.8200
C18—C231.389 (4)O4—C241.208 (3)
C18—C171.486 (4)C30—C251.389 (4)
C7—H7A0.9600C30—C291.392 (4)
C7—H7B0.9600C30—H300.9300
C7—H7C0.9600C29—C281.382 (4)
C3—C51.526 (4)C29—H290.9300
C3—C41.537 (4)C24—C251.492 (4)
C3—H3A0.9800C25—C261.380 (4)
C5—H5A0.9700C26—C271.384 (4)
C5—H5B0.9700C26—H260.9300
C23—C221.391 (4)C27—C281.383 (4)
C23—H230.9300C27—H270.9300
C15—H15A0.9600C28—H280.9300
C15—H15B0.9600
N2—Ni1—N4104.28 (8)C14—C15—H15B109.5
N2—Ni1—O2156.80 (8)H15A—C15—H15B109.5
N4—Ni1—O298.91 (8)C14—C15—H15C109.5
N2—Ni1—N185.74 (8)H15A—C15—H15C109.5
N4—Ni1—N190.70 (8)H15B—C15—H15C109.5
O2—Ni1—N194.56 (8)N4—C10—C9109.1 (2)
N2—Ni1—N391.05 (8)N4—C10—H10A109.9
N4—Ni1—N384.99 (8)C9—C10—H10A109.9
O2—Ni1—N390.46 (8)N4—C10—H10B109.9
N1—Ni1—N3173.84 (8)C9—C10—H10B109.9
N2—Ni1—O196.06 (8)H10A—C10—H10B108.3
N4—Ni1—O1159.39 (8)N1—C1—C2110.1 (2)
O2—Ni1—O160.82 (7)N1—C1—H1A109.6
N1—Ni1—O187.49 (7)C2—C1—H1A109.6
N3—Ni1—O198.09 (7)N1—C1—H1B109.6
O7—Cl1—O5109.69 (14)C2—C1—H1B109.6
O7—Cl1—O8110.04 (18)H1A—C1—H1B108.1
O5—Cl1—O8110.78 (15)N2—C2—C1109.4 (2)
O7—Cl1—O6109.14 (18)N2—C2—H2A109.8
O5—Cl1—O6109.81 (14)C1—C2—H2A109.8
O8—Cl1—O6107.34 (14)N2—C2—H2B109.8
C9—N3—C6113.71 (19)C1—C2—H2B109.8
C9—N3—Ni1104.21 (14)H2A—C2—H2B108.2
C6—N3—Ni1120.59 (15)C11—C13—C14118.4 (2)
C9—N3—H3C105.7C11—C13—H13A107.7
C6—N3—H3C105.7C14—C13—H13A107.7
Ni1—N3—H3C105.7C11—C13—H13B107.7
C1—N1—C14113.5 (2)C14—C13—H13B107.7
C1—N1—Ni1103.69 (15)H13A—C13—H13B107.1
C14—N1—Ni1121.68 (15)C6—C8—H8A109.5
C1—N1—H1C105.6C6—C8—H8B109.5
C14—N1—H1C105.6H8A—C8—H8B109.5
Ni1—N1—H1C105.6C6—C8—H8C109.5
C17—O1—Ni186.98 (15)H8A—C8—H8C109.5
C17—O2—Ni191.82 (16)H8B—C8—H8C109.5
C11—N4—C10112.8 (2)C20—C19—C18120.2 (3)
C11—N4—Ni1115.40 (15)C20—C19—H19119.9
C10—N4—Ni1104.85 (15)C18—C19—H19119.9
C11—N4—H4D107.8C3—C4—H4A109.5
C10—N4—H4D107.8C3—C4—H4B109.5
Ni1—N4—H4D107.8H4A—C4—H4B109.5
C2—N2—C3112.9 (2)C3—C4—H4C109.5
C2—N2—Ni1104.20 (15)H4A—C4—H4C109.5
C3—N2—Ni1117.77 (16)H4B—C4—H4C109.5
C2—N2—H2C107.1C14—C16—H16A109.5
C3—N2—H2C107.1C14—C16—H16B109.5
Ni1—N2—H2C107.1H16A—C16—H16B109.5
N3—C6—C8108.1 (2)C14—C16—H16C109.5
N3—C6—C5109.5 (2)H16A—C16—H16C109.5
C8—C6—C5111.6 (2)H16B—C16—H16C109.5
N3—C6—C7111.7 (2)N4—C11—C12113.5 (2)
C8—C6—C7108.0 (2)N4—C11—C13110.4 (2)
C5—C6—C7107.9 (2)C12—C11—C13109.2 (2)
N1—C14—C13110.5 (2)N4—C11—H11107.8
N1—C14—C15107.9 (2)C12—C11—H11107.8
C13—C14—C15110.9 (2)C13—C11—H11107.8
N1—C14—C16111.3 (2)C11—C12—H12A109.5
C13—C14—C16108.7 (2)C11—C12—H12B109.5
C15—C14—C16107.5 (2)H12A—C12—H12B109.5
N3—C9—C10109.3 (2)C11—C12—H12C109.5
N3—C9—H9A109.8H12A—C12—H12C109.5
C10—C9—H9A109.8H12B—C12—H12C109.5
N3—C9—H9B109.8C21—C20—C19119.8 (3)
C10—C9—H9B109.8C21—C20—H20120.1
H9A—C9—H9B108.3C19—C20—H20120.1
C19—C18—C23119.5 (3)C21—C22—C23120.2 (3)
C19—C18—C17120.0 (2)C21—C22—H22119.9
C23—C18—C17120.5 (2)C23—C22—H22119.9
O2—C17—O1120.2 (2)C22—C21—C20120.4 (3)
O2—C17—C18120.2 (2)C22—C21—H21119.8
O1—C17—C18119.6 (2)C20—C21—H21119.8
C6—C7—H7A109.5C24—O3—H3B109.5
C6—C7—H7B109.5C25—C30—C29119.3 (3)
H7A—C7—H7B109.5C25—C30—H30120.3
C6—C7—H7C109.5C29—C30—H30120.3
H7A—C7—H7C109.5C28—C29—C30119.9 (3)
H7B—C7—H7C109.5C28—C29—H29120.0
N2—C3—C5111.1 (2)C30—C29—H29120.0
N2—C3—C4112.3 (2)O4—C24—O3123.2 (2)
C5—C3—C4108.5 (2)O4—C24—C25122.2 (2)
N2—C3—H3A108.3O3—C24—C25114.7 (2)
C5—C3—H3A108.3C26—C25—C30120.4 (2)
C4—C3—H3A108.3C26—C25—C24117.7 (2)
C3—C5—C6119.9 (2)C30—C25—C24121.8 (2)
C3—C5—H5A107.3C25—C26—C27120.2 (3)
C6—C5—H5A107.3C25—C26—H26119.9
C3—C5—H5B107.3C27—C26—H26119.9
C6—C5—H5B107.3C28—C27—C26119.6 (3)
H5A—C5—H5B106.9C28—C27—H27120.2
C18—C23—C22119.8 (3)C26—C27—H27120.2
C18—C23—H23120.1C29—C28—C27120.5 (3)
C22—C23—H23120.1C29—C28—H28119.7
C14—C15—H15A109.5C27—C28—H28119.7
N2—Ni1—N3—C990.62 (16)Ni1—N1—C14—C15−74.8 (2)
N4—Ni1—N3—C9−13.62 (16)C1—N1—C14—C1642.7 (3)
O2—Ni1—N3—C9−112.53 (16)Ni1—N1—C14—C16167.49 (17)
N1—Ni1—N3—C932.1 (8)C6—N3—C9—C10174.9 (2)
O1—Ni1—N3—C9−173.10 (15)Ni1—N3—C9—C1041.7 (2)
N2—Ni1—N3—C6−38.55 (19)Ni1—O2—C17—O14.4 (2)
N4—Ni1—N3—C6−142.79 (19)Ni1—O2—C17—C18−174.22 (19)
O2—Ni1—N3—C6118.30 (18)Ni1—O1—C17—O2−4.2 (2)
N1—Ni1—N3—C6−97.1 (8)Ni1—O1—C17—C18174.4 (2)
O1—Ni1—N3—C657.73 (19)C19—C18—C17—O236.7 (4)
N2—Ni1—N1—C1−11.37 (16)C23—C18—C17—O2−144.8 (3)
N4—Ni1—N1—C192.90 (16)C19—C18—C17—O1−141.9 (2)
O2—Ni1—N1—C1−168.10 (16)C23—C18—C17—O136.6 (4)
N3—Ni1—N1—C147.4 (8)C2—N2—C3—C5179.6 (2)
O1—Ni1—N1—C1−107.64 (16)Ni1—N2—C3—C5−58.8 (3)
N2—Ni1—N1—C14−140.56 (19)C2—N2—C3—C457.9 (3)
N4—Ni1—N1—C14−36.29 (19)Ni1—N2—C3—C4179.49 (17)
O2—Ni1—N1—C1462.71 (19)N2—C3—C5—C670.1 (3)
N3—Ni1—N1—C14−81.8 (8)C4—C3—C5—C6−166.0 (2)
O1—Ni1—N1—C14123.17 (18)N3—C6—C5—C3−64.4 (3)
N2—Ni1—O1—C17−179.64 (13)C8—C6—C5—C355.3 (3)
N4—Ni1—O1—C17−8.9 (3)C7—C6—C5—C3173.8 (2)
O2—Ni1—O1—C172.45 (13)C19—C18—C23—C22−1.6 (4)
N1—Ni1—O1—C17−94.19 (14)C17—C18—C23—C22179.9 (3)
N3—Ni1—O1—C1788.43 (14)C11—N4—C10—C9170.4 (2)
N2—Ni1—O2—C17−7.8 (3)Ni1—N4—C10—C944.0 (2)
N4—Ni1—O2—C17173.50 (14)N3—C9—C10—N4−60.2 (3)
N1—Ni1—O2—C1782.07 (15)C14—N1—C1—C2173.4 (2)
N3—Ni1—O2—C17−101.50 (14)Ni1—N1—C1—C239.4 (2)
O1—Ni1—O2—C17−2.48 (13)C3—N2—C2—C1173.9 (2)
N2—Ni1—N4—C11129.24 (18)Ni1—N2—C2—C145.0 (2)
O2—Ni1—N4—C11−51.27 (18)N1—C1—C2—N2−59.7 (3)
N1—Ni1—N4—C1143.46 (18)N1—C14—C13—C11−62.5 (3)
N3—Ni1—N4—C11−140.95 (18)C15—C14—C13—C1157.1 (3)
O1—Ni1—N4—C11−41.3 (3)C16—C14—C13—C11175.1 (2)
N2—Ni1—N4—C10−106.03 (16)C23—C18—C19—C20−0.4 (4)
O2—Ni1—N4—C1073.46 (16)C17—C18—C19—C20178.1 (2)
N1—Ni1—N4—C10168.18 (16)C10—N4—C11—C1251.8 (3)
N3—Ni1—N4—C10−16.22 (16)Ni1—N4—C11—C12172.2 (2)
O1—Ni1—N4—C1083.5 (3)C10—N4—C11—C13174.8 (2)
N4—Ni1—N2—C2−107.64 (16)Ni1—N4—C11—C13−64.7 (2)
O2—Ni1—N2—C273.6 (3)C14—C13—C11—N474.4 (3)
N1—Ni1—N2—C2−18.00 (16)C14—C13—C11—C12−160.1 (2)
N3—Ni1—N2—C2167.26 (16)C18—C19—C20—C211.1 (4)
O1—Ni1—N2—C269.01 (16)C18—C23—C22—C213.1 (5)
N4—Ni1—N2—C3126.38 (17)C23—C22—C21—C20−2.5 (5)
O2—Ni1—N2—C3−52.3 (3)C19—C20—C21—C220.4 (5)
N1—Ni1—N2—C3−143.98 (18)C25—C30—C29—C280.2 (4)
N3—Ni1—N2—C341.29 (18)C29—C30—C25—C260.2 (4)
O1—Ni1—N2—C3−56.96 (18)C29—C30—C25—C24178.1 (3)
C9—N3—C6—C8163.9 (2)O4—C24—C25—C262.7 (5)
Ni1—N3—C6—C8−71.2 (2)O3—C24—C25—C26−177.2 (3)
C9—N3—C6—C5−74.3 (3)O4—C24—C25—C30−175.3 (3)
Ni1—N3—C6—C550.6 (3)O3—C24—C25—C304.8 (4)
C9—N3—C6—C745.2 (3)C30—C25—C26—C27−0.8 (4)
Ni1—N3—C6—C7170.07 (17)C24—C25—C26—C27−178.8 (3)
C1—N1—C14—C13−78.2 (3)C25—C26—C27—C281.0 (5)
Ni1—N1—C14—C1346.7 (3)C30—C29—C28—C270.0 (5)
C1—N1—C14—C15160.4 (2)C26—C27—C28—C29−0.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1C···O4i0.912.072.970 (3)171
N4—H4D···O6ii0.912.133.001 (3)161
O3—H3B···O1iii0.821.872.691 (3)174
N3—H3C···O80.912.223.108 (3)166
N2—H2C···O6ii0.912.253.123 (3)160

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2117).

References

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  • Jiang, L., Feng, X. L. & Lu, T. B. (2005). Cryst. Growth Des. 5, 1469–1475.
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