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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1010.
Published online 2008 July 9. doi:  10.1107/S1600536808020564
PMCID: PMC2961933

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

Abstract

The Ni atom in the title salt, [Ni(C7H5O2)(C16H36N4)]ClO4·H2O, is in a six-coordinate octa­hedral geometry. The metal atom is chelated by the carboxyl­ate group, and the macrocyclic ligand adopts a folded configuration. The cation, anion and water mol­ecules engage in hydrogen bonding to form a layer structure.

Related literature

For related literature, see: Jiang et al. (2005 [triangle]); Ou et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1010-scheme1.jpg

Experimental

Crystal data

  • [Ni(C7H5O2)(C16H36N4)]ClO4·H2O
  • M r = 581.77
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1010-efi1.jpg
  • a = 15.1239 (14) Å
  • b = 8.9351 (8) Å
  • c = 20.9918 (19) Å
  • β = 102.414 (2)°
  • V = 2770.4 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.84 mm−1
  • T = 173 (2) K
  • 0.48 × 0.40 × 0.21 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.688, T max = 0.843
  • 15892 measured reflections
  • 6007 independent reflections
  • 4802 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.121
  • S = 1.10
  • 6007 reflections
  • 337 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [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
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020564/ng2469sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020564/ng2469Isup2.hkl

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

Acknowledgments

This work was supported financially by the Foundation for University Key Teachers of the Education Department of Hunan Province, and the Key Subject Construction Project of Hunan Province (grant No. 2006-180).

supplementary crystallographic information

Comment

It's 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 (Jiang et al., 2005). A racemic nickel(II) complex with cis-conformation can be separated to two enantiomers by the reactions of [Ni(rac-L)]2+ with chiral amino acid such as phenylalanine (Ou et al., 2008). Then we employ no chiral benzoic acid as separation reagent, but the result of experiment indicate a racemic complex of [Ni(rac-L)(bz)(ClO4)]H2O is obtained instead of two enantiomers. In the asymmetric unit of (I), contains one [Ni(rac-L)(bz)]+ cation, one [ClO4]- anion and one water molecule. As illustrated in Fig.1, The six-coordinated Ni2+ of [Ni(rac-L)(bz)]+ cation display a distorted octahedral geometry by coordination with four N atoms of macrocyclic ligand L in a folded configuration, and two carboxylate oxygen atoms of benzoic acid in cis-position. The Ni—N distances ranging from 2.086 (19) to 2.133 (19) Å, are slight shorter than the Ni—O distance [2.138 (17) to 2.170 (16) Å] (Table 1). Neighbouring cations and anions are discrete, connected to each other through two intermolecular hydrogen bond (Table 2), water and oxygen atom of benzoato anion, and water and oxygen atom of [ClO4]- anion (See Fig. 2).

Experimental

benzoic acid (H2bz, 0.122 g, 1 mmol) was mixed with NaOH (0.040 g, 1 mmol) dissolved in 10 ml of water. To this solution was added [Ni(rac-L)](ClO4)2 (0.541 g, 1 mmol) dissolved in a minimum amount of CH3CN. The solution was left to stand at room temperature and blue crystals formed after several weeks(yield 53%).

Refinement

H atoms attached to O (water) atoms were located in difference Fourier maps and condtrained to ride on their carrier atoms, with O—H distances in the range 0.82 Å, and with Uiso (H) = 1.5 times Ueq (O).

Figures

Fig. 1.
The molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
Fig. 2.
Two intermolecular hydrogen bond, O1w and O2 of benzoato anion, and O1w and O6 of [ClO4]- anion.

Crystal data

[Ni(C7H5O2)(C16H36N4)]ClO4·H2OF000 = 1240
Mr = 581.77Dx = 1.395 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8118 reflections
a = 15.1239 (14) Åθ = 2.7–27.1º
b = 8.9351 (8) ŵ = 0.84 mm1
c = 20.9918 (19) ÅT = 173 (2) K
β = 102.414 (2)ºBlock, blue
V = 2770.4 (4) Å30.48 × 0.40 × 0.21 mm
Z = 4

Data collection

Bruker SMART diffractometer6007 independent reflections
Radiation source: fine-focus sealed tube4802 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 173(2) Kθmax = 27.1º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −16→19
Tmin = 0.688, Tmax = 0.843k = −11→11
15892 measured reflectionsl = −26→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121  w = 1/[σ2(Fo2) + (0.0673P)2 + 1.378P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
6007 reflectionsΔρmax = 0.43 e Å3
337 parametersΔρmin = −0.44 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
Ni10.250097 (18)0.59158 (3)0.132452 (13)0.01980 (10)
N40.15871 (13)0.4136 (2)0.11775 (9)0.0229 (4)
H4D0.16850.35750.15590.027*
O10.30893 (11)0.79837 (19)0.11139 (8)0.0256 (4)
O20.20094 (11)0.69355 (18)0.03764 (8)0.0256 (4)
N10.16886 (12)0.7161 (2)0.18507 (9)0.0226 (4)
H1C0.18390.81590.18060.027*
N30.33157 (13)0.4525 (2)0.08693 (9)0.0237 (4)
H3A0.32280.48680.04420.028*
N20.33164 (12)0.5457 (2)0.22499 (9)0.0209 (4)
H2C0.31110.45620.23920.025*
C90.20586 (16)0.6787 (3)0.25445 (11)0.0259 (5)
H9A0.17990.58280.26530.031*
H9B0.18900.75770.28270.031*
C180.27474 (16)0.9066 (3)0.00497 (11)0.0233 (5)
C170.26017 (15)0.7949 (3)0.05489 (11)0.0232 (5)
C100.30721 (16)0.6661 (3)0.26643 (12)0.0277 (5)
H10A0.33330.76230.25600.033*
H10B0.33210.64310.31300.033*
C130.45580 (16)0.4159 (3)0.18539 (12)0.0273 (5)
H13A0.42540.32120.19240.033*
H13B0.52180.39760.19820.033*
C110.43209 (15)0.5309 (3)0.23209 (11)0.0249 (5)
H110.45660.63000.22210.030*
C20.18611 (17)0.3218 (3)0.06704 (12)0.0296 (5)
H2A0.16640.37080.02400.036*
H2B0.15660.22250.06500.036*
C140.43295 (16)0.4485 (3)0.11189 (12)0.0273 (5)
C160.47053 (18)0.5992 (3)0.09632 (14)0.0355 (6)
H16A0.53650.59970.11170.053*
H16B0.44390.67910.11820.053*
H16C0.45530.61580.04910.053*
C30.06071 (15)0.4551 (3)0.10069 (12)0.0273 (5)
H30.04990.51830.06040.033*
C80.02322 (18)0.7801 (3)0.21821 (14)0.0375 (6)
H8A0.03470.71640.25710.056*
H8B−0.04220.78920.20140.056*
H8C0.04910.87960.22960.056*
C50.03588 (16)0.5467 (3)0.15609 (13)0.0300 (5)
H5A−0.03090.54620.14960.036*
H5B0.06000.49310.19740.036*
C210.3060 (2)1.1047 (3)−0.08971 (13)0.0344 (6)
H210.31681.1726−0.12200.041*
C230.20363 (17)0.9519 (3)−0.04531 (13)0.0318 (6)
H230.14430.9144−0.04750.038*
C220.21979 (19)1.0518 (3)−0.09210 (13)0.0368 (6)
H220.17121.0839−0.12590.044*
C200.37688 (18)1.0589 (3)−0.04021 (13)0.0313 (6)
H200.43651.0940−0.03910.038*
C10.28810 (17)0.3027 (3)0.08246 (13)0.0312 (6)
H1A0.30760.24880.12430.037*
H1B0.30660.24320.04780.037*
C70.03832 (18)0.8008 (3)0.10272 (13)0.0362 (6)
H7A0.05330.90650.11180.054*
H7B−0.02710.79040.08630.054*
H7C0.07030.76380.06990.054*
C190.36099 (16)0.9624 (3)0.00744 (12)0.0278 (5)
H190.40940.93400.04220.033*
C120.47882 (18)0.4865 (3)0.30144 (12)0.0351 (6)
H12A0.46290.55840.33240.053*
H12B0.54460.48660.30540.053*
H12C0.45900.38620.31100.053*
C4−0.00056 (18)0.3171 (3)0.08730 (14)0.0389 (7)
H4A0.01250.26200.05000.058*
H4B−0.06410.34880.07740.058*
H4C0.01070.25230.12590.058*
C60.06727 (15)0.7097 (3)0.16554 (11)0.0266 (5)
C150.47577 (19)0.3267 (3)0.07671 (13)0.0375 (6)
H15A0.54190.33570.08850.056*
H15B0.45500.33860.02940.056*
H15C0.45780.22790.08970.056*
O1W0.2792 (2)0.5335 (4)−0.05895 (13)0.0872 (11)
H1D0.246 (3)0.505 (7)−0.0943 (18)0.131*
H1E0.238 (3)0.581 (6)−0.045 (3)0.131*
Cl10.23445 (4)0.37222 (7)−0.24307 (3)0.03201 (16)
O30.21061 (14)0.2166 (2)−0.24210 (9)0.0415 (5)
O50.19455 (19)0.4317 (2)−0.30582 (11)0.0585 (7)
O40.32947 (18)0.3837 (4)−0.23043 (17)0.0865 (10)
O60.1992 (2)0.4479 (3)−0.19397 (11)0.0654 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.01889 (16)0.02163 (17)0.01882 (16)−0.00185 (11)0.00392 (11)0.00090 (11)
N40.0240 (10)0.0251 (10)0.0189 (9)−0.0024 (8)0.0033 (8)0.0007 (7)
O10.0255 (8)0.0277 (9)0.0232 (8)−0.0025 (7)0.0043 (7)0.0029 (7)
O20.0244 (8)0.0258 (9)0.0255 (8)−0.0029 (7)0.0032 (7)0.0017 (7)
N10.0207 (9)0.0227 (10)0.0246 (10)−0.0001 (8)0.0057 (8)0.0002 (8)
N30.0209 (9)0.0282 (11)0.0224 (10)−0.0001 (8)0.0056 (8)0.0008 (8)
N20.0192 (9)0.0232 (10)0.0198 (9)−0.0005 (7)0.0034 (7)0.0013 (7)
C90.0291 (12)0.0268 (13)0.0226 (11)0.0015 (10)0.0074 (9)−0.0020 (9)
C180.0246 (11)0.0233 (12)0.0235 (11)0.0021 (9)0.0083 (9)0.0006 (9)
C170.0201 (11)0.0244 (12)0.0256 (11)0.0035 (9)0.0063 (9)0.0003 (9)
C100.0284 (13)0.0283 (13)0.0245 (12)0.0003 (10)0.0012 (10)−0.0041 (10)
C130.0232 (12)0.0300 (13)0.0276 (12)0.0031 (9)0.0034 (10)0.0012 (10)
C110.0208 (11)0.0282 (13)0.0249 (12)−0.0010 (9)0.0028 (9)0.0030 (9)
C20.0296 (13)0.0339 (14)0.0257 (12)−0.0074 (10)0.0067 (10)−0.0093 (10)
C140.0221 (12)0.0329 (13)0.0282 (12)0.0024 (10)0.0082 (10)0.0010 (10)
C160.0263 (13)0.0443 (17)0.0367 (15)−0.0027 (11)0.0090 (11)0.0089 (12)
C30.0193 (11)0.0340 (14)0.0269 (12)−0.0038 (10)0.0015 (9)−0.0004 (10)
C80.0302 (13)0.0434 (17)0.0420 (16)0.0040 (12)0.0142 (12)−0.0067 (12)
C50.0205 (12)0.0370 (14)0.0331 (13)−0.0047 (10)0.0073 (10)−0.0024 (11)
C210.0448 (16)0.0312 (14)0.0316 (14)0.0048 (11)0.0182 (12)0.0095 (11)
C230.0252 (12)0.0350 (14)0.0343 (14)−0.0005 (10)0.0042 (10)0.0050 (11)
C220.0345 (14)0.0425 (16)0.0311 (14)0.0068 (12)0.0018 (11)0.0102 (12)
C200.0285 (13)0.0333 (14)0.0353 (14)−0.0006 (11)0.0138 (11)0.0035 (11)
C10.0333 (14)0.0250 (13)0.0377 (14)−0.0004 (10)0.0129 (11)−0.0067 (10)
C70.0269 (13)0.0417 (16)0.0378 (14)0.0092 (11)0.0023 (11)0.0027 (12)
C190.0234 (12)0.0320 (13)0.0284 (12)0.0027 (10)0.0066 (10)0.0046 (10)
C120.0290 (13)0.0463 (17)0.0266 (13)0.0064 (12)−0.0017 (10)0.0001 (12)
C40.0270 (13)0.0446 (17)0.0444 (16)−0.0144 (12)0.0060 (11)−0.0119 (13)
C60.0212 (11)0.0329 (14)0.0253 (12)0.0016 (10)0.0045 (9)−0.0017 (10)
C150.0332 (14)0.0447 (17)0.0371 (15)0.0087 (12)0.0134 (11)0.0004 (12)
O1W0.108 (3)0.104 (2)0.0420 (15)0.051 (2)−0.0002 (15)−0.0162 (15)
Cl10.0377 (3)0.0263 (3)0.0303 (3)0.0022 (2)0.0035 (3)−0.0017 (2)
O30.0604 (13)0.0272 (10)0.0369 (10)−0.0006 (9)0.0105 (9)0.0005 (8)
O50.096 (2)0.0360 (12)0.0376 (12)0.0114 (12)0.0018 (12)0.0082 (9)
O40.0395 (14)0.112 (3)0.104 (2)−0.0220 (15)0.0060 (15)0.0054 (19)
O60.097 (2)0.0534 (15)0.0436 (13)0.0220 (14)0.0098 (13)−0.0208 (11)

Geometric parameters (Å, °)

Ni1—N42.0859 (19)C16—H16C0.9800
Ni1—N22.1053 (18)C3—C41.532 (3)
Ni1—N32.117 (2)C3—C51.533 (4)
Ni1—N12.1333 (19)C3—H31.0000
Ni1—O12.1379 (17)C8—C61.542 (3)
Ni1—O22.1698 (16)C8—H8A0.9800
N4—C21.472 (3)C8—H8B0.9800
N4—C31.495 (3)C8—H8C0.9800
N4—H4D0.9300C5—C61.531 (4)
O1—C171.255 (3)C5—H5A0.9900
O2—C171.271 (3)C5—H5B0.9900
N1—C91.482 (3)C21—C221.377 (4)
N1—C61.504 (3)C21—C201.385 (4)
N1—H1C0.9300C21—H210.9500
N3—C11.485 (3)C23—C221.387 (4)
N3—C141.510 (3)C23—H230.9500
N3—H3A0.9300C22—H220.9500
N2—C101.480 (3)C20—C191.380 (3)
N2—C111.500 (3)C20—H200.9500
N2—H2C0.9300C1—H1A0.9900
C9—C101.503 (3)C1—H1B0.9900
C9—H9A0.9900C7—C61.531 (4)
C9—H9B0.9900C7—H7A0.9800
C18—C191.387 (3)C7—H7B0.9800
C18—C231.395 (3)C7—H7C0.9800
C18—C171.497 (3)C19—H190.9500
C10—H10A0.9900C12—H12A0.9800
C10—H10B0.9900C12—H12B0.9800
C13—C111.515 (3)C12—H12C0.9800
C13—C141.535 (3)C4—H4A0.9800
C13—H13A0.9900C4—H4B0.9800
C13—H13B0.9900C4—H4C0.9800
C11—C121.528 (3)C15—H15A0.9800
C11—H111.0000C15—H15B0.9800
C2—C11.516 (3)C15—H15C0.9800
C2—H2A0.9900O1W—H1D0.844 (19)
C2—H2B0.9900O1W—H1E0.86 (2)
C14—C161.524 (4)Cl1—O41.408 (3)
C14—C151.535 (4)Cl1—O51.428 (2)
C16—H16A0.9800Cl1—O61.428 (2)
C16—H16B0.9800Cl1—O31.437 (2)
N4—Ni1—N2103.07 (8)C16—C14—C15108.0 (2)
N4—Ni1—N385.25 (8)C13—C14—C15108.8 (2)
N2—Ni1—N391.14 (7)C14—C16—H16A109.5
N4—Ni1—N192.13 (8)C14—C16—H16B109.5
N2—Ni1—N184.96 (7)H16A—C16—H16B109.5
N3—Ni1—N1174.71 (8)C14—C16—H16C109.5
N4—Ni1—O1156.97 (7)H16A—C16—H16C109.5
N2—Ni1—O199.89 (7)H16B—C16—H16C109.5
N3—Ni1—O196.05 (7)N4—C3—C4111.9 (2)
N1—Ni1—O188.16 (7)N4—C3—C5110.04 (19)
N4—Ni1—O295.68 (7)C4—C3—C5109.4 (2)
N2—Ni1—O2160.97 (7)N4—C3—H3108.5
N3—Ni1—O287.15 (7)C4—C3—H3108.5
N1—Ni1—O297.70 (7)C5—C3—H3108.5
O1—Ni1—O261.52 (6)C6—C8—H8A109.5
C2—N4—C3112.56 (18)C6—C8—H8B109.5
C2—N4—Ni1104.54 (14)H8A—C8—H8B109.5
C3—N4—Ni1115.95 (15)C6—C8—H8C109.5
C2—N4—H4D107.8H8A—C8—H8C109.5
C3—N4—H4D107.8H8B—C8—H8C109.5
Ni1—N4—H4D107.8C6—C5—C3119.1 (2)
C17—O1—Ni189.32 (14)C6—C5—H5A107.5
C17—O2—Ni187.50 (13)C3—C5—H5A107.5
C9—N1—C6114.04 (17)C6—C5—H5B107.5
C9—N1—Ni1104.68 (13)C3—C5—H5B107.5
C6—N1—Ni1120.50 (14)H5A—C5—H5B107.0
C9—N1—H1C105.5C22—C21—C20120.0 (2)
C6—N1—H1C105.5C22—C21—H21120.0
Ni1—N1—H1C105.5C20—C21—H21120.0
C1—N3—C14113.78 (19)C22—C23—C18119.9 (2)
C1—N3—Ni1105.34 (14)C22—C23—H23120.1
C14—N3—Ni1120.21 (15)C18—C23—H23120.1
C1—N3—H3A105.4C21—C22—C23120.3 (2)
C14—N3—H3A105.4C21—C22—H22119.9
Ni1—N3—H3A105.4C23—C22—H22119.9
C10—N2—C11112.42 (18)C19—C20—C21120.0 (2)
C10—N2—Ni1103.31 (14)C19—C20—H20120.0
C11—N2—Ni1119.26 (14)C21—C20—H20120.0
C10—N2—H2C107.1N3—C1—C2109.2 (2)
C11—N2—H2C107.1N3—C1—H1A109.8
Ni1—N2—H2C107.1C2—C1—H1A109.8
N1—C9—C10109.72 (18)N3—C1—H1B109.8
N1—C9—H9A109.7C2—C1—H1B109.8
C10—C9—H9A109.7H1A—C1—H1B108.3
N1—C9—H9B109.7C6—C7—H7A109.5
C10—C9—H9B109.7C6—C7—H7B109.5
H9A—C9—H9B108.2H7A—C7—H7B109.5
C19—C18—C23119.3 (2)C6—C7—H7C109.5
C19—C18—C17119.5 (2)H7A—C7—H7C109.5
C23—C18—C17121.1 (2)H7B—C7—H7C109.5
O1—C17—O2121.4 (2)C20—C19—C18120.4 (2)
O1—C17—C18120.0 (2)C20—C19—H19119.8
O2—C17—C18118.5 (2)C18—C19—H19119.8
O1—C17—Ni160.09 (12)C11—C12—H12A109.5
O2—C17—Ni161.52 (12)C11—C12—H12B109.5
C18—C17—Ni1172.92 (16)H12A—C12—H12B109.5
N2—C10—C9109.31 (19)C11—C12—H12C109.5
N2—C10—H10A109.8H12A—C12—H12C109.5
C9—C10—H10A109.8H12B—C12—H12C109.5
N2—C10—H10B109.8C3—C4—H4A109.5
C9—C10—H10B109.8C3—C4—H4B109.5
H10A—C10—H10B108.3H4A—C4—H4B109.5
C11—C13—C14119.2 (2)C3—C4—H4C109.5
C11—C13—H13A107.5H4A—C4—H4C109.5
C14—C13—H13A107.5H4B—C4—H4C109.5
C11—C13—H13B107.5N1—C6—C7107.51 (19)
C14—C13—H13B107.5N1—C6—C5109.96 (19)
H13A—C13—H13B107.0C7—C6—C5111.7 (2)
N2—C11—C13111.78 (19)N1—C6—C8111.26 (19)
N2—C11—C12111.64 (19)C7—C6—C8108.2 (2)
C13—C11—C12108.4 (2)C5—C6—C8108.1 (2)
N2—C11—H11108.3C14—C15—H15A109.5
C13—C11—H11108.3C14—C15—H15B109.5
C12—C11—H11108.3H15A—C15—H15B109.5
N4—C2—C1109.87 (19)C14—C15—H15C109.5
N4—C2—H2A109.7H15A—C15—H15C109.5
C1—C2—H2A109.7H15B—C15—H15C109.5
N4—C2—H2B109.7H1D—O1W—H1E96 (5)
C1—C2—H2B109.7O4—Cl1—O5110.99 (19)
H2A—C2—H2B108.2O4—Cl1—O6110.70 (19)
N3—C14—C16107.6 (2)O5—Cl1—O6109.89 (15)
N3—C14—C13110.23 (19)O4—Cl1—O3108.47 (17)
C16—C14—C13111.7 (2)O5—Cl1—O3108.38 (13)
N3—C14—C15110.6 (2)O6—Cl1—O3108.32 (15)
N2—Ni1—N4—C2−108.67 (15)C19—C18—C17—O2−145.7 (2)
N3—Ni1—N4—C2−18.60 (15)C23—C18—C17—O232.2 (3)
N1—Ni1—N4—C2166.01 (15)N4—Ni1—C17—O1174.52 (12)
O1—Ni1—N4—C275.7 (2)N2—Ni1—C17—O1−9.01 (17)
O2—Ni1—N4—C268.05 (15)N3—Ni1—C17—O1−100.98 (13)
C17—Ni1—N4—C268.56 (17)N1—Ni1—C17—O178.34 (14)
N2—Ni1—N4—C3126.78 (15)O2—Ni1—C17—O1175.5 (2)
N3—Ni1—N4—C3−143.15 (16)N4—Ni1—C17—O2−0.99 (17)
N1—Ni1—N4—C341.46 (16)N2—Ni1—C17—O2175.48 (12)
O1—Ni1—N4—C3−48.8 (3)N3—Ni1—C17—O283.51 (13)
O2—Ni1—N4—C3−56.50 (16)N1—Ni1—C17—O2−97.16 (13)
C17—Ni1—N4—C3−55.99 (18)O1—Ni1—C17—O2−175.5 (2)
N4—Ni1—O1—C17−11.3 (3)C11—N2—C10—C9177.47 (19)
N2—Ni1—O1—C17173.02 (13)Ni1—N2—C10—C947.6 (2)
N3—Ni1—O1—C1780.80 (14)N1—C9—C10—N2−60.6 (3)
N1—Ni1—O1—C17−102.42 (14)C10—N2—C11—C13−175.36 (19)
O2—Ni1—O1—C17−2.63 (13)Ni1—N2—C11—C13−54.3 (2)
N4—Ni1—O2—C17179.21 (13)C10—N2—C11—C1263.1 (3)
N2—Ni1—O2—C17−10.6 (3)Ni1—N2—C11—C12−175.85 (17)
N3—Ni1—O2—C17−95.85 (14)C14—C13—C11—N268.1 (3)
N1—Ni1—O2—C1786.27 (14)C14—C13—C11—C12−168.4 (2)
O1—Ni1—O2—C172.60 (12)C3—N4—C2—C1171.8 (2)
N4—Ni1—N1—C993.70 (15)Ni1—N4—C2—C145.1 (2)
N2—Ni1—N1—C9−9.24 (14)C1—N3—C14—C16164.6 (2)
O1—Ni1—N1—C9−109.34 (14)Ni1—N3—C14—C16−69.1 (2)
O2—Ni1—N1—C9−170.27 (14)C1—N3—C14—C13−73.3 (2)
C17—Ni1—N1—C9−139.25 (14)Ni1—N3—C14—C1352.9 (2)
N4—Ni1—N1—C6−36.32 (17)C1—N3—C14—C1547.0 (3)
N2—Ni1—N1—C6−139.26 (17)Ni1—N3—C14—C15173.21 (16)
O1—Ni1—N1—C6120.64 (17)C11—C13—C14—N3−66.7 (3)
O2—Ni1—N1—C659.71 (17)C11—C13—C14—C1652.9 (3)
C17—Ni1—N1—C690.73 (17)C11—C13—C14—C15171.9 (2)
N4—Ni1—N3—C1−10.58 (15)C2—N4—C3—C456.6 (3)
N2—Ni1—N3—C192.45 (15)Ni1—N4—C3—C4176.92 (17)
O1—Ni1—N3—C1−167.48 (15)C2—N4—C3—C5178.5 (2)
O2—Ni1—N3—C1−106.52 (15)Ni1—N4—C3—C5−61.2 (2)
C17—Ni1—N3—C1−137.33 (15)N4—C3—C5—C674.1 (3)
N4—Ni1—N3—C14−140.64 (17)C4—C3—C5—C6−162.6 (2)
N2—Ni1—N3—C14−37.62 (17)C19—C18—C23—C220.0 (4)
O1—Ni1—N3—C1462.45 (17)C17—C18—C23—C22−177.9 (2)
O2—Ni1—N3—C14123.41 (17)C20—C21—C22—C23−0.4 (4)
N4—Ni1—N2—C10−111.54 (15)C18—C23—C22—C211.0 (4)
N3—Ni1—N2—C10163.07 (15)C22—C21—C20—C19−1.2 (4)
N1—Ni1—N2—C10−20.52 (14)C14—N3—C1—C2171.41 (19)
O1—Ni1—N2—C1066.73 (15)Ni1—N3—C1—C237.7 (2)
O2—Ni1—N2—C1078.5 (3)N4—C2—C1—N3−58.1 (3)
C17—Ni1—N2—C1071.37 (17)C21—C20—C19—C182.2 (4)
N4—Ni1—N2—C11122.90 (17)C23—C18—C19—C20−1.6 (4)
N3—Ni1—N2—C1137.51 (17)C17—C18—C19—C20176.3 (2)
N1—Ni1—N2—C11−146.08 (17)C9—N1—C6—C7160.6 (2)
O1—Ni1—N2—C11−58.84 (17)Ni1—N1—C6—C7−73.6 (2)
O2—Ni1—N2—C11−47.1 (3)C9—N1—C6—C5−77.6 (2)
C6—N1—C9—C10171.69 (19)Ni1—N1—C6—C548.2 (2)
Ni1—N1—C9—C1038.0 (2)C9—N1—C6—C842.2 (3)
Ni1—O1—C17—O24.6 (2)Ni1—N1—C6—C8168.01 (17)
Ni1—O1—C17—C18−171.82 (19)C3—C5—C6—N1−65.4 (3)
Ni1—O2—C17—O1−4.6 (2)C3—C5—C6—C753.9 (3)
C19—C18—C17—O130.9 (3)C3—C5—C6—C8172.9 (2)
C23—C18—C17—O1−151.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O1W0.932.163.080 (3)168
O1W—H1D···O60.844 (19)2.12 (3)2.934 (4)162 (6)
O1W—H1E···O20.86 (2)2.18 (4)2.931 (3)146 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2469).

References

  • Bruker (1999). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jiang, L., Feng, X. L. & Lu, T. B. (2005). Cryst. Growth Des.5, 1469–1475.
  • Ou, G. C., Jiang, L., Feng, X. L. & Lu, T. B. (2008). Inorg. Chem.47, 2710–2718. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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