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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Jul 21;68(Pt 8):m1100. doi: 10.1107/S1600536812032175

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

Qiang Gao a,*, Yi-Cheng Cao a
PMCID: PMC3414150  PMID: 22904757

Abstract

In the title compound, [Ni(C9H7O2)(C16H36N4)]ClO4·H2O, the macrocyclic 5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane ligand (L) folds around the NiII atom, which is also chelated by the carboxyl­ate group. The geometry is a distorted N4O2 octa­hedron. In the crystal, adjacent mol­ecules are connected by O—H⋯O and N—H⋯O hydrogen bonds into a zigzag chain parallel to [010].

Related literature  

For background to this study, see: Tait & Busch (1976 ▶); Curtis (1965 ▶). For related structures, see: Ou et al. (2008 ▶, 2009a ▶,b ▶); Ou & Ng 2010a ▶,b ▶).graphic file with name e-68-m1100-scheme1.jpg

Experimental  

Crystal data  

  • [Ni(C9H7O2)(C16H36N4)]ClO4·H2O

  • M r = 607.81

  • Monoclinic, Inline graphic

  • a = 10.6903 (11) Å

  • b = 14.5396 (8) Å

  • c = 19.2498 (12) Å

  • β = 94.225 (6)°

  • V = 2983.9 (4) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 2.16 mm−1

  • T = 153 K

  • 0.42 × 0.21 × 0.16 mm

Data collection  

  • Agilent Xcalibur Atlas Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.464, T max = 0.724

  • 10750 measured reflections

  • 5001 independent reflections

  • 4533 reflections with I > 2σ(I)

  • R int = 0.022

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.038

  • wR(F 2) = 0.098

  • S = 1.04

  • 5001 reflections

  • 355 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.53 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032175/ds2203sup1.cif

e-68-m1100-sup1.cif (31KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032175/ds2203Isup2.hkl

e-68-m1100-Isup2.hkl (245KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4D⋯O1W i 0.93 2.11 3.009 (2) 163
N2—H2C⋯O1W i 0.93 2.19 3.073 (2) 158
O1W—H1WA⋯O1ii 0.80 (3) 1.94 (3) 2.732 (2) 173 (3)
O1W—H1WB⋯O5 0.80 (3) 2.13 (3) 2.921 (3) 171 (3)
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Acknowledgments

The authors thank the National Foundation of Natural Science of China (No. 90412015) and the Key Project of Science and Technology of Guangzhou City (2005Z12E4023) for financial support.

supplementary crystallographic information

Comment

Similar other nickel salts involving the macrocyclic ligand L were reported (Ou et al., 2008, 2009a, 2009b, 2010a, 2010b). The asymmetric unit in the title compound contains one [NiL(C6H5C2H2CO2)]+, one [ClO4]- and one free water molecule. In each cation (Fig. 1), the nickel(II) ion displays a distorted octahedral coordination geometry by coordination with four nitrogen atoms of L in a folded conformation, and two carboxylate oxygen atoms of cinnamic acid in cis position. Adjacent molecules are connected through the O—H···O (2.732 (2)–2.921 (3) Å) and N—H···O (3.009 (2)–3.073 (2) Å) (Table 1) hydrogen bonding interactions between the carboxylate oxygen atom of cinnamic acid, oxygen atom of water molecule and secondary amine of L, generating a zigzag chain (Figs. 2, 3).

Experimental

A solution of [Ni(rac-L)](ClO4)2 (0.541 g, 1 mmol) in acetonitrile (10 ml) was added to a solution of cinnamic acid (0.148 g, 1 mmol) and NaOH (0.040 g, 1 mmol) in 10 ml of water. The resultant blue solution was evaporated slowly at room temperature. After several weeks, violet prism-shaped crystals were obtained.

Refinement

H atoms bound to carbon, oxygen and nitrogen atoms were positioned geometrically and refined using the riding model, and with C—H = 0.95 to 1.00 Å, O—H = 0.80 Å and N—H = 0.93 Å, and with U(H) set to 1.2 to 1.5 Ueq(C, O, N).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Fig. 2.

Fig. 2.

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A view of the packing of the title compound

Fig. 3.

Fig. 3.

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Hydrogen bonding (dashed lines) of the title compound

Crystal data

[Ni(C9H7O2)(C16H36N4)]ClO4·H2O F(000) = 1296
Mr = 607.81 Dx = 1.353 Mg m−3
Monoclinic, P21/n Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn Cell parameters from 10750 reflections
a = 10.6903 (11) Å θ = 3.8–65.5°
b = 14.5396 (8) Å µ = 2.16 mm−1
c = 19.2498 (12) Å T = 153 K
β = 94.225 (6)° Prism, violet
V = 2983.9 (4) Å3 0.42 × 0.21 × 0.16 mm
Z = 4
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Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer 5001 independent reflections
Radiation source: fine-focus sealed tube 4533 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.022
ω scans θmax = 65.5°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) h = −9→12
Tmin = 0.464, Tmax = 0.724 k = −15→16
10750 measured reflections l = −20→22
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098 H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0494P)2 + 2.0261P] where P = (Fo2 + 2Fc2)/3
5001 reflections (Δ/σ)max = 0.001
355 parameters Δρmax = 0.67 e Å−3
0 restraints Δρmin = −0.53 e Å−3
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Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.15 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Ni1 0.82693 (3) 0.10829 (2) 0.168866 (17) 0.01820 (11)
Cl1 0.37923 (5) 0.79143 (4) 0.11605 (3) 0.03427 (15)
O1W 0.65932 (16) 0.88699 (11) 0.21653 (9) 0.0329 (4)
N4 0.71496 (15) 0.08543 (12) 0.25076 (9) 0.0215 (4)
H4D 0.6875 0.0248 0.2477 0.026*
N3 0.98016 (15) 0.07735 (12) 0.24375 (9) 0.0226 (4)
H3A 1.0142 0.1338 0.2578 0.027*
N1 0.66694 (16) 0.12951 (11) 0.09671 (9) 0.0224 (4)
H1C 0.6945 0.1679 0.0623 0.027*
O1 0.86371 (13) 0.25222 (10) 0.18630 (7) 0.0246 (3)
O2 0.93361 (13) 0.17771 (9) 0.09782 (7) 0.0234 (3)
N2 0.83993 (15) −0.01980 (11) 0.12133 (8) 0.0199 (4)
H2C 0.7974 −0.0624 0.1469 0.024*
C7 1.1671 (2) 0.07934 (17) 0.17803 (13) 0.0336 (5)
H7A 1.1139 0.1024 0.1382 0.050*
H7B 1.2356 0.0426 0.1612 0.050*
H7C 1.2021 0.1313 0.2054 0.050*
C18 0.99490 (19) 0.33452 (14) 0.11318 (11) 0.0254 (5)
H18 0.9782 0.3914 0.1349 0.030*
C9 0.9196 (2) 0.04063 (18) 0.30456 (11) 0.0305 (5)
H9A 0.9776 0.0462 0.3469 0.037*
H9B 0.8998 −0.0253 0.2972 0.037*
C13 0.51412 (19) 0.13204 (15) 0.18830 (12) 0.0271 (5)
H13A 0.5027 0.0651 0.1809 0.033*
H13B 0.4314 0.1574 0.1982 0.033*
O5 0.4206 (2) 0.88266 (13) 0.13241 (12) 0.0614 (6)
C12 0.5291 (2) 0.12492 (19) 0.31703 (13) 0.0379 (6)
H12A 0.4976 0.0616 0.3144 0.057*
H12B 0.4584 0.1677 0.3178 0.057*
H12C 0.5844 0.1326 0.3596 0.057*
O3 0.29831 (17) 0.79250 (13) 0.05395 (9) 0.0459 (5)
O6 0.3166 (3) 0.75420 (18) 0.17151 (11) 0.0832 (8)
C6 1.08899 (19) 0.01963 (15) 0.22362 (11) 0.0266 (5)
C11 0.60231 (19) 0.14496 (15) 0.25364 (11) 0.0258 (5)
H11 0.6302 0.2106 0.2559 0.031*
C8 1.1740 (2) −0.00999 (18) 0.28747 (13) 0.0366 (6)
H8A 1.1962 0.0440 0.3163 0.055*
H8B 1.2505 −0.0382 0.2721 0.055*
H8C 1.1295 −0.0546 0.3148 0.055*
C5 1.0409 (2) −0.06705 (15) 0.18454 (11) 0.0265 (5)
H5A 1.1141 −0.1071 0.1781 0.032*
H5B 0.9860 −0.1006 0.2151 0.032*
C14 0.54944 (19) 0.17362 (15) 0.11962 (12) 0.0280 (5)
C15 0.5743 (2) 0.27698 (16) 0.12686 (14) 0.0378 (6)
H15A 0.6482 0.2872 0.1592 0.057*
H15B 0.5013 0.3071 0.1448 0.057*
H15C 0.5895 0.3028 0.0812 0.057*
C2 0.7687 (2) −0.00750 (15) 0.05307 (11) 0.0255 (5)
H2A 0.7540 −0.0681 0.0306 0.031*
H2B 0.8180 0.0306 0.0224 0.031*
C17 0.92733 (18) 0.25108 (14) 0.13254 (11) 0.0224 (4)
O4 0.4837 (2) 0.73377 (18) 0.10554 (16) 0.0933 (9)
C16 0.4378 (2) 0.15948 (18) 0.06591 (13) 0.0381 (6)
H16A 0.4606 0.1801 0.0201 0.057*
H16B 0.3659 0.1952 0.0797 0.057*
H16C 0.4157 0.0941 0.0637 0.057*
C23 1.3114 (4) 0.5501 (3) 0.00822 (16) 0.0737 (12)
H23 1.3664 0.5986 −0.0024 0.088*
C1 0.64498 (19) 0.03845 (14) 0.06257 (11) 0.0254 (5)
H1A 0.5981 0.0468 0.0167 0.031*
H1B 0.5941 −0.0008 0.0917 0.031*
C20 1.1556 (2) 0.40741 (16) 0.04353 (11) 0.0275 (5)
C24 1.3420 (3) 0.4605 (3) −0.00655 (14) 0.0672 (11)
H24 1.4168 0.4479 −0.0286 0.081*
C21 1.1246 (3) 0.49896 (16) 0.05564 (12) 0.0368 (6)
H21 1.0489 0.5128 0.0763 0.044*
C10 0.8008 (2) 0.09348 (17) 0.31431 (11) 0.0307 (5)
H10A 0.7598 0.0687 0.3548 0.037*
H10B 0.8210 0.1590 0.3235 0.037*
C25 1.2639 (2) 0.3878 (2) 0.01061 (12) 0.0411 (6)
H25 1.2847 0.3261 −0.0001 0.049*
C4 0.9680 (2) −0.14652 (17) 0.07386 (13) 0.0389 (6)
H4A 0.9174 −0.1917 0.0971 0.058*
H4B 1.0540 −0.1695 0.0727 0.058*
H4C 0.9319 −0.1367 0.0262 0.058*
C3 0.96907 (19) −0.05558 (14) 0.11380 (11) 0.0243 (4)
H3 1.0147 −0.0093 0.0868 0.029*
C22 1.2023 (3) 0.5696 (2) 0.03801 (14) 0.0595 (10)
H22 1.1800 0.6316 0.0465 0.071*
C19 1.07876 (19) 0.33104 (14) 0.06586 (11) 0.0228 (4)
H19 1.0902 0.2732 0.0443 0.027*
H1WA 0.657 (2) 0.8500 (19) 0.2470 (14) 0.034*
H1WB 0.597 (3) 0.8806 (18) 0.1911 (14) 0.034*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Ni1 0.01681 (19) 0.01662 (19) 0.02133 (19) −0.00561 (13) 0.00246 (13) −0.00172 (13)
Cl1 0.0359 (3) 0.0264 (3) 0.0385 (3) −0.0035 (2) −0.0111 (2) 0.0074 (2)
O1W 0.0335 (9) 0.0305 (9) 0.0336 (9) −0.0151 (7) −0.0042 (7) 0.0111 (7)
N4 0.0191 (8) 0.0208 (9) 0.0248 (9) −0.0045 (7) 0.0038 (7) −0.0013 (7)
N3 0.0202 (9) 0.0248 (9) 0.0229 (9) −0.0049 (7) 0.0026 (7) −0.0053 (7)
N1 0.0225 (9) 0.0182 (9) 0.0263 (9) −0.0052 (7) 0.0008 (7) 0.0026 (7)
O1 0.0242 (7) 0.0212 (7) 0.0293 (8) −0.0070 (6) 0.0086 (6) −0.0051 (6)
O2 0.0259 (7) 0.0185 (7) 0.0263 (7) −0.0071 (6) 0.0058 (6) −0.0049 (6)
N2 0.0193 (8) 0.0197 (8) 0.0205 (8) −0.0054 (7) 0.0008 (7) −0.0008 (7)
C7 0.0186 (11) 0.0387 (13) 0.0441 (14) −0.0068 (10) 0.0061 (10) −0.0040 (11)
C18 0.0269 (11) 0.0164 (10) 0.0334 (12) −0.0068 (9) 0.0058 (9) −0.0038 (9)
C9 0.0253 (11) 0.0448 (14) 0.0211 (11) 0.0014 (10) 0.0008 (9) 0.0028 (10)
C13 0.0173 (10) 0.0253 (11) 0.0391 (13) −0.0035 (8) 0.0038 (9) −0.0034 (10)
O5 0.0721 (14) 0.0309 (10) 0.0761 (15) −0.0172 (10) −0.0277 (12) 0.0059 (10)
C12 0.0270 (12) 0.0488 (15) 0.0394 (14) −0.0043 (11) 0.0138 (10) −0.0077 (12)
O3 0.0502 (11) 0.0433 (11) 0.0412 (10) −0.0115 (9) −0.0168 (8) 0.0114 (8)
O6 0.121 (2) 0.0837 (18) 0.0447 (13) −0.0476 (16) 0.0012 (13) 0.0221 (12)
C6 0.0177 (10) 0.0306 (12) 0.0314 (12) −0.0001 (9) 0.0008 (9) −0.0048 (9)
C11 0.0203 (10) 0.0228 (11) 0.0351 (12) −0.0038 (9) 0.0067 (9) −0.0027 (9)
C8 0.0232 (11) 0.0477 (15) 0.0376 (13) 0.0025 (10) −0.0056 (10) −0.0055 (11)
C5 0.0218 (10) 0.0264 (11) 0.0311 (12) 0.0022 (9) 0.0006 (9) −0.0022 (9)
C14 0.0208 (10) 0.0236 (11) 0.0391 (13) 0.0001 (9) −0.0009 (9) 0.0024 (10)
C15 0.0353 (13) 0.0215 (12) 0.0563 (16) 0.0028 (10) 0.0016 (11) 0.0055 (11)
C2 0.0278 (11) 0.0241 (11) 0.0235 (11) −0.0029 (9) −0.0045 (8) −0.0040 (9)
C17 0.0189 (10) 0.0195 (10) 0.0289 (11) −0.0066 (8) 0.0031 (8) −0.0013 (9)
O4 0.0641 (15) 0.0748 (17) 0.136 (3) 0.0368 (14) −0.0290 (16) −0.0102 (16)
C16 0.0265 (12) 0.0396 (14) 0.0468 (15) 0.0053 (11) −0.0062 (10) 0.0038 (11)
C23 0.097 (3) 0.085 (3) 0.0373 (16) −0.071 (2) −0.0065 (17) 0.0221 (17)
C1 0.0245 (11) 0.0227 (11) 0.0278 (11) −0.0059 (9) −0.0065 (9) −0.0022 (9)
C20 0.0298 (12) 0.0336 (12) 0.0185 (10) −0.0150 (10) −0.0024 (8) 0.0028 (9)
C24 0.0511 (18) 0.121 (3) 0.0305 (14) −0.052 (2) 0.0080 (12) 0.0054 (17)
C21 0.0532 (15) 0.0282 (12) 0.0274 (12) −0.0194 (11) −0.0085 (11) 0.0051 (10)
C10 0.0257 (11) 0.0440 (14) 0.0229 (11) 0.0004 (10) 0.0041 (9) −0.0024 (10)
C25 0.0330 (13) 0.0656 (18) 0.0248 (12) −0.0198 (12) 0.0034 (10) 0.0052 (12)
C4 0.0389 (13) 0.0328 (13) 0.0437 (14) 0.0087 (11) −0.0050 (11) −0.0144 (11)
C3 0.0220 (10) 0.0238 (11) 0.0273 (11) −0.0012 (9) 0.0030 (8) −0.0042 (9)
C22 0.097 (3) 0.0437 (17) 0.0341 (14) −0.0435 (17) −0.0206 (16) 0.0173 (13)
C19 0.0238 (10) 0.0198 (10) 0.0247 (10) −0.0067 (8) 0.0004 (8) −0.0022 (8)
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Geometric parameters (Å, º)

Ni1—N4 2.0752 (17) C12—H12C 0.9800
Ni1—N2 2.0841 (17) C6—C8 1.535 (3)
Ni1—O2 2.1023 (14) C6—C5 1.537 (3)
Ni1—N1 2.1447 (17) C11—H11 1.0000
Ni1—N3 2.1485 (17) C8—H8A 0.9800
Ni1—O1 2.1512 (14) C8—H8B 0.9800
Ni1—C17 2.462 (2) C8—H8C 0.9800
Cl1—O6 1.409 (2) C5—C3 1.522 (3)
Cl1—O4 1.422 (2) C5—H5A 0.9900
Cl1—O3 1.4231 (17) C5—H5B 0.9900
Cl1—O5 1.4260 (19) C14—C15 1.531 (3)
O1W—H1WA 0.80 (3) C14—C16 1.534 (3)
O1W—H1WB 0.80 (3) C15—H15A 0.9800
N4—C10 1.479 (3) C15—H15B 0.9800
N4—C11 1.487 (3) C15—H15C 0.9800
N4—H4D 0.9300 C2—C1 1.505 (3)
N3—C9 1.478 (3) C2—H2A 0.9900
N3—C6 1.508 (3) C2—H2B 0.9900
N3—H3A 0.9300 C16—H16A 0.9800
N1—C1 1.489 (3) C16—H16B 0.9800
N1—C14 1.505 (3) C16—H16C 0.9800
N1—H1C 0.9300 C23—C22 1.367 (5)
O1—C17 1.280 (2) C23—C24 1.378 (6)
O2—C17 1.263 (2) C23—H23 0.9500
N2—C2 1.480 (3) C1—H1A 0.9900
N2—C3 1.492 (3) C1—H1B 0.9900
N2—H2C 0.9300 C20—C25 1.390 (3)
C7—C6 1.526 (3) C20—C21 1.395 (3)
C7—H7A 0.9800 C20—C19 1.464 (3)
C7—H7B 0.9800 C24—C25 1.402 (4)
C7—H7C 0.9800 C24—H24 0.9500
C18—C19 1.325 (3) C21—C22 1.379 (4)
C18—C17 1.474 (3) C21—H21 0.9500
C18—H18 0.9500 C10—H10A 0.9900
C9—C10 1.508 (3) C10—H10B 0.9900
C9—H9A 0.9900 C25—H25 0.9500
C9—H9B 0.9900 C4—C3 1.529 (3)
C13—C14 1.526 (3) C4—H4A 0.9800
C13—C11 1.527 (3) C4—H4B 0.9800
C13—H13A 0.9900 C4—H4C 0.9800
C13—H13B 0.9900 C3—H3 1.0000
C12—C11 1.525 (3) C22—H22 0.9500
C12—H12A 0.9800 C19—H19 0.9500
C12—H12B 0.9800
N4—Ni1—N2 104.55 (7) N4—C11—H11 108.5
N4—Ni1—O2 160.39 (6) C12—C11—H11 108.5
N2—Ni1—O2 94.96 (6) C13—C11—H11 108.5
N4—Ni1—N1 92.18 (7) C6—C8—H8A 109.5
N2—Ni1—N1 85.41 (6) C6—C8—H8B 109.5
O2—Ni1—N1 87.40 (6) H8A—C8—H8B 109.5
N4—Ni1—N3 84.88 (6) C6—C8—H8C 109.5
N2—Ni1—N3 92.02 (7) H8A—C8—H8C 109.5
O2—Ni1—N3 96.52 (6) H8B—C8—H8C 109.5
N1—Ni1—N3 175.49 (6) C3—C5—C6 118.46 (18)
N4—Ni1—O1 98.41 (6) C3—C5—H5A 107.7
N2—Ni1—O1 157.00 (6) C6—C5—H5A 107.7
O2—Ni1—O1 62.14 (5) C3—C5—H5B 107.7
N1—Ni1—O1 95.11 (6) C6—C5—H5B 107.7
N3—Ni1—O1 88.70 (6) H5A—C5—H5B 107.1
N4—Ni1—C17 129.70 (7) N1—C14—C13 110.50 (17)
N2—Ni1—C17 125.75 (7) N1—C14—C15 107.56 (17)
O2—Ni1—C17 30.87 (6) C13—C14—C15 111.3 (2)
N1—Ni1—C17 92.19 (7) N1—C14—C16 111.70 (18)
N3—Ni1—C17 92.31 (7) C13—C14—C16 107.52 (18)
O1—Ni1—C17 31.29 (6) C15—C14—C16 108.32 (19)
O6—Cl1—O4 107.63 (19) C14—C15—H15A 109.5
O6—Cl1—O3 110.32 (13) C14—C15—H15B 109.5
O4—Cl1—O3 108.77 (15) H15A—C15—H15B 109.5
O6—Cl1—O5 110.30 (15) C14—C15—H15C 109.5
O4—Cl1—O5 110.23 (15) H15A—C15—H15C 109.5
O3—Cl1—O5 109.56 (11) H15B—C15—H15C 109.5
H1WA—O1W—H1WB 107 (3) N2—C2—C1 110.18 (17)
C10—N4—C11 112.21 (16) N2—C2—H2A 109.6
C10—N4—Ni1 104.95 (12) C1—C2—H2A 109.6
C11—N4—Ni1 116.68 (13) N2—C2—H2B 109.6
C10—N4—H4D 107.5 C1—C2—H2B 109.6
C11—N4—H4D 107.5 H2A—C2—H2B 108.1
Ni1—N4—H4D 107.5 O2—C17—O1 119.40 (18)
C9—N3—C6 113.18 (17) O2—C17—C18 121.02 (18)
C9—N3—Ni1 104.49 (12) O1—C17—C18 119.56 (18)
C6—N3—Ni1 120.57 (12) O2—C17—Ni1 58.63 (10)
C9—N3—H3A 105.8 O1—C17—Ni1 60.82 (10)
C6—N3—H3A 105.8 C18—C17—Ni1 176.35 (15)
Ni1—N3—H3A 105.8 C14—C16—H16A 109.5
C1—N1—C14 113.60 (16) C14—C16—H16B 109.5
C1—N1—Ni1 104.49 (12) H16A—C16—H16B 109.5
C14—N1—Ni1 120.96 (13) C14—C16—H16C 109.5
C1—N1—H1C 105.5 H16A—C16—H16C 109.5
C14—N1—H1C 105.5 H16B—C16—H16C 109.5
Ni1—N1—H1C 105.5 C22—C23—C24 120.4 (3)
C17—O1—Ni1 87.89 (11) C22—C23—H23 119.8
C17—O2—Ni1 90.50 (12) C24—C23—H23 119.8
C2—N2—C3 112.02 (16) N1—C1—C2 109.69 (16)
C2—N2—Ni1 103.61 (12) N1—C1—H1A 109.7
C3—N2—Ni1 116.50 (12) C2—C1—H1A 109.7
C2—N2—H2C 108.1 N1—C1—H1B 109.7
C3—N2—H2C 108.1 C2—C1—H1B 109.7
Ni1—N2—H2C 108.1 H1A—C1—H1B 108.2
C6—C7—H7A 109.5 C25—C20—C21 119.2 (2)
C6—C7—H7B 109.5 C25—C20—C19 118.8 (2)
H7A—C7—H7B 109.5 C21—C20—C19 122.0 (2)
C6—C7—H7C 109.5 C23—C24—C25 120.7 (3)
H7A—C7—H7C 109.5 C23—C24—H24 119.7
H7B—C7—H7C 109.5 C25—C24—H24 119.7
C19—C18—C17 120.75 (19) C22—C21—C20 121.0 (3)
C19—C18—H18 119.6 C22—C21—H21 119.5
C17—C18—H18 119.6 C20—C21—H21 119.5
N3—C9—C10 109.66 (18) N4—C10—C9 109.51 (17)
N3—C9—H9A 109.7 N4—C10—H10A 109.8
C10—C9—H9A 109.7 C9—C10—H10A 109.8
N3—C9—H9B 109.7 N4—C10—H10B 109.8
C10—C9—H9B 109.7 C9—C10—H10B 109.8
H9A—C9—H9B 108.2 H10A—C10—H10B 108.2
C14—C13—C11 119.19 (17) C20—C25—C24 118.9 (3)
C14—C13—H13A 107.5 C20—C25—H25 120.6
C11—C13—H13A 107.5 C24—C25—H25 120.6
C14—C13—H13B 107.5 C3—C4—H4A 109.5
C11—C13—H13B 107.5 C3—C4—H4B 109.5
H13A—C13—H13B 107.0 H4A—C4—H4B 109.5
C11—C12—H12A 109.5 C3—C4—H4C 109.5
C11—C12—H12B 109.5 H4A—C4—H4C 109.5
H12A—C12—H12B 109.5 H4B—C4—H4C 109.5
C11—C12—H12C 109.5 N2—C3—C5 111.13 (16)
H12A—C12—H12C 109.5 N2—C3—C4 112.18 (17)
H12B—C12—H12C 109.5 C5—C3—C4 109.85 (18)
N3—C6—C7 107.25 (18) N2—C3—H3 107.8
N3—C6—C8 111.87 (17) C5—C3—H3 107.8
C7—C6—C8 107.64 (18) C4—C3—H3 107.8
N3—C6—C5 110.21 (16) C23—C22—C21 119.8 (3)
C7—C6—C5 111.26 (18) C23—C22—H22 120.1
C8—C6—C5 108.59 (19) C21—C22—H22 120.1
N4—C11—C12 112.52 (19) C18—C19—C20 126.5 (2)
N4—C11—C13 110.49 (17) C18—C19—H19 116.7
C12—C11—C13 108.28 (17) C20—C19—H19 116.7
N2—Ni1—N4—C10 109.46 (13) C10—N4—C11—C12 −56.9 (2)
O2—Ni1—N4—C10 −76.4 (2) Ni1—N4—C11—C12 −177.99 (14)
N1—Ni1—N4—C10 −164.72 (14) C10—N4—C11—C13 −178.01 (17)
N3—Ni1—N4—C10 18.70 (14) Ni1—N4—C11—C13 60.86 (19)
O1—Ni1—N4—C10 −69.22 (14) C14—C13—C11—N4 −74.0 (2)
C17—Ni1—N4—C10 −70.05 (16) C14—C13—C11—C12 162.3 (2)
N2—Ni1—N4—C11 −125.64 (14) N3—C6—C5—C3 65.4 (2)
O2—Ni1—N4—C11 48.5 (3) C7—C6—C5—C3 −53.4 (2)
N1—Ni1—N4—C11 −39.82 (14) C8—C6—C5—C3 −171.74 (18)
N3—Ni1—N4—C11 143.60 (14) C1—N1—C14—C13 79.9 (2)
O1—Ni1—N4—C11 55.67 (14) Ni1—N1—C14—C13 −45.6 (2)
C17—Ni1—N4—C11 54.85 (16) C1—N1—C14—C15 −158.53 (18)
N4—Ni1—N3—C9 10.68 (14) Ni1—N1—C14—C15 76.0 (2)
N2—Ni1—N3—C9 −93.76 (14) C1—N1—C14—C16 −39.8 (2)
O2—Ni1—N3—C9 171.01 (13) Ni1—N1—C14—C16 −165.28 (15)
N1—Ni1—N3—C9 −38.6 (9) C11—C13—C14—N1 64.3 (2)
O1—Ni1—N3—C9 109.24 (14) C11—C13—C14—C15 −55.1 (3)
C17—Ni1—N3—C9 140.33 (14) C11—C13—C14—C16 −173.57 (19)
N4—Ni1—N3—C6 139.34 (15) C3—N2—C2—C1 −173.67 (16)
N2—Ni1—N3—C6 34.91 (15) Ni1—N2—C2—C1 −47.29 (18)
O2—Ni1—N3—C6 −60.32 (15) Ni1—O2—C17—O1 −2.56 (19)
N1—Ni1—N3—C6 90.1 (8) Ni1—O2—C17—C18 175.75 (18)
O1—Ni1—N3—C6 −122.09 (15) Ni1—O1—C17—O2 2.50 (19)
C17—Ni1—N3—C6 −91.00 (15) Ni1—O1—C17—C18 −175.83 (18)
N4—Ni1—N1—C1 −96.07 (13) C19—C18—C17—O2 −10.4 (3)
N2—Ni1—N1—C1 8.36 (13) C19—C18—C17—O1 167.9 (2)
O2—Ni1—N1—C1 103.55 (13) C19—C18—C17—Ni1 73 (3)
N3—Ni1—N1—C1 −47.0 (9) N4—Ni1—C17—O2 −175.87 (11)
O1—Ni1—N1—C1 165.28 (12) N2—Ni1—C17—O2 4.71 (15)
C17—Ni1—N1—C1 134.05 (13) N1—Ni1—C17—O2 −81.22 (12)
N4—Ni1—N1—C14 33.51 (15) N3—Ni1—C17—O2 98.87 (12)
N2—Ni1—N1—C14 137.94 (15) O1—Ni1—C17—O2 −177.45 (19)
O2—Ni1—N1—C14 −126.86 (14) N4—Ni1—C17—O1 1.57 (15)
N3—Ni1—N1—C14 82.6 (8) N2—Ni1—C17—O1 −177.85 (10)
O1—Ni1—N1—C14 −65.14 (14) O2—Ni1—C17—O1 177.45 (19)
C17—Ni1—N1—C14 −96.36 (15) N1—Ni1—C17—O1 96.23 (12)
N4—Ni1—O1—C17 −178.78 (12) N3—Ni1—C17—O1 −83.69 (12)
N2—Ni1—O1—C17 4.5 (2) N4—Ni1—C17—C18 99 (2)
O2—Ni1—O1—C17 −1.48 (11) N2—Ni1—C17—C18 −81 (2)
N1—Ni1—O1—C17 −85.81 (12) O2—Ni1—C17—C18 −86 (2)
N3—Ni1—O1—C17 96.60 (12) N1—Ni1—C17—C18 −167 (2)
N4—Ni1—O2—C17 9.5 (2) N3—Ni1—C17—C18 13 (2)
N2—Ni1—O2—C17 −176.17 (12) O1—Ni1—C17—C18 97 (2)
N1—Ni1—O2—C17 98.67 (12) C14—N1—C1—C2 −170.05 (17)
N3—Ni1—O2—C17 −83.56 (12) Ni1—N1—C1—C2 −36.21 (18)
O1—Ni1—O2—C17 1.50 (11) N2—C2—C1—N1 59.0 (2)
N4—Ni1—N2—C2 111.64 (12) C22—C23—C24—C25 −2.0 (5)
O2—Ni1—N2—C2 −66.40 (12) C25—C20—C21—C22 −2.6 (3)
N1—Ni1—N2—C2 20.58 (12) C19—C20—C21—C22 176.0 (2)
N3—Ni1—N2—C2 −163.13 (12) C11—N4—C10—C9 −173.26 (18)
O1—Ni1—N2—C2 −71.7 (2) Ni1—N4—C10—C9 −45.6 (2)
C17—Ni1—N2—C2 −68.82 (14) N3—C9—C10—N4 59.0 (2)
N4—Ni1—N2—C3 −124.88 (14) C21—C20—C25—C24 2.9 (3)
O2—Ni1—N2—C3 57.08 (14) C19—C20—C25—C24 −175.7 (2)
N1—Ni1—N2—C3 144.06 (14) C23—C24—C25—C20 −0.7 (4)
N3—Ni1—N2—C3 −39.65 (14) C2—N2—C3—C5 179.60 (17)
O1—Ni1—N2—C3 51.8 (2) Ni1—N2—C3—C5 60.6 (2)
C17—Ni1—N2—C3 54.66 (16) C2—N2—C3—C4 −57.0 (2)
C6—N3—C9—C10 −171.36 (17) Ni1—N2—C3—C4 −176.01 (15)
Ni1—N3—C9—C10 −38.4 (2) C6—C5—C3—N2 −74.0 (2)
C9—N3—C6—C7 −161.79 (17) C6—C5—C3—C4 161.30 (19)
Ni1—N3—C6—C7 73.53 (19) C24—C23—C22—C21 2.3 (4)
C9—N3—C6—C8 −44.0 (2) C20—C21—C22—C23 0.0 (4)
Ni1—N3—C6—C8 −168.65 (15) C17—C18—C19—C20 −177.7 (2)
C9—N3—C6—C5 77.0 (2) C25—C20—C19—C18 160.3 (2)
Ni1—N3—C6—C5 −47.7 (2) C21—C20—C19—C18 −18.4 (3)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
N4—H4D···O1Wi 0.93 2.11 3.009 (2) 163
N2—H2C···O1Wi 0.93 2.19 3.073 (2) 158
O1W—H1WA···O1ii 0.80 (3) 1.94 (3) 2.732 (2) 173 (3)
O1W—H1WB···O5 0.80 (3) 2.13 (3) 2.921 (3) 171 (3)
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Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2203).

References

  1. Agilent (2011). CrysAlis PRO Agilent Technologies Ltd, Yarnton, England.
  2. Curtis, N. F. (1965). J. Chem. Soc. A, pp. 924–931.
  3. Ou, G.-C. & Ng, S. W. (2010a). Acta Cryst. E66, m1295–m1296. [DOI] [PMC free article] [PubMed]
  4. Ou, G.-C. & Ng, S. W. (2010b). Acta Cryst. E66, m1468. [DOI] [PMC free article] [PubMed]
  5. Ou, G.-C., Zhang, M. & Yuan, X.-Y. (2008). Acta Cryst. E64, m1010. [DOI] [PMC free article] [PubMed]
  6. Ou, G.-C., Zhang, M. & Yuan, X.-Y. (2009a). Acta Cryst. E65, m726. [DOI] [PMC free article] [PubMed]
  7. Ou, G.-C., Zhou, Q. & Ng, S. W. (2009b). Acta Cryst. E65, m728. [DOI] [PMC free article] [PubMed]
  8. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  9. Tait, A. M. & Busch, D. H. (1976). Inorg. Synth. 18, 4–7.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032175/ds2203sup1.cif

e-68-m1100-sup1.cif (31KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032175/ds2203Isup2.hkl

e-68-m1100-Isup2.hkl (245KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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