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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1295–m1296.
Published online 2010 September 25. doi:  10.1107/S1600536810037116
PMCID: PMC2983378

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

Abstract

In the title salt, [Ni(C7H6NO2)(C16H36N4)]ClO4·H2O, the NiII cation is O,O′-chelated by the benzoate anion and N,N′,N′′,N′′′-chelated by the macrocycle ligand, confering a distorted octa­hedral geometry on the metal atom. The complex cations, perchlorate anions and uncoordinated water mol­ecules are linked by N—H(...)O and O—H(...)O hydrogen bonds into a three-dimensional network. The perchlorate ion is disordered over two positions in a 0.554 (8):0.446 (8) ratio.

Related literature

For two related structures, see: Ou et al. (2008a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1295-scheme1.jpg

Experimental

Crystal data

  • [Ni(C7H6NO2)(C16H36N4)]ClO4·H2O
  • M r = 596.79
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1295-efi1.jpg
  • a = 9.6452 (5) Å
  • b = 21.5350 (11) Å
  • c = 13.5083 (7) Å
  • β = 90.784 (1)°
  • V = 2805.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.84 mm−1
  • T = 110 K
  • 0.45 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.818, T max = 1.000
  • 6638 measured reflections
  • 3832 independent reflections
  • 3667 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.064
  • S = 1.08
  • 3832 reflections
  • 410 parameters
  • 142 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.21 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 874 Friedel pairs
  • Flack parameter: −0.012 (9)

Data collection: SMART (Bruker, 2003 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037116/xu5028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037116/xu5028Isup2.hkl

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

Acknowledgments

We thank the Key Subject Construction Project of Hunan Province (No. 2006–180), the Key Scientific Research Project of Hunan Provincial Education Department (No. 08 A023, 05 C736), the NSF of Hunan Province (09 J J3028) and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Previous studies on (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)nickel benzoate perchlorate salts have documented a chelating mode for the carboxylate ion. The perchlorate counterion is not directly involved in coordination but forms hydrogen bonds with the amino portions of the macrocycle (Ou et al., 2008a, 2008b). The title substituted benzoate has an additional amino unit that also engages in hydrogen bonding. In the salt, [Ni(C16H36N4)(C7H6NO2)][ClO4].H2O (Scheme I, Fig. 1), the metal atom is O,O'-chelated by the carboxylate anion and N,N',N'',N'''-chelated by the macrocycle to confer an octahedral geometry to the metal center. The cation, anion and lattice water molecules are linked by N–H···O and O–H···O hydrogen bonds into a three-dimensional network.

Experimental

Anthranilic acid (0.27 g, 2 mmol) and sodium hydroxide (0.08 g, 2 mmol) were dissolved in water (15 ml). To this solution was added (rac-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)nickel diperchlorate (0.11 g, 2 mmol) dissolved in acetonitrile (10 ml). The solution was set aside for the growth of violet crystals after a few days.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95–1.00 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

The water and amino H atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 Å and N–H 0.86±0.01 Å. For the water molecule, the H···H distance was restrained to 1.37±0.01 Å. The temperature factors were tied to those of the parent atoms by a factor of 1.2–1.5 times.

The perchlorate is disordered over two positions in a 0.554 (8):0.446 (8) ratio. All Cl–O distances were restrained to within 0.01 Å of each other as were the O···O distances. The anisotropic temperature factors of the O atoms were restrained to be nearly isotropic.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [Ni(C16H36N4)(C7H6NO2)][ClO4].H2O at the 50% probability level; hydrogen atoms are shown as spheres of arbitrary radius. The disorder in the perchlorate is not shown.

Crystal data

[Ni(C7H6NO2)(C16H36N4)]ClO4·H2OF(000) = 1272
Mr = 596.79Dx = 1.413 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 5267 reflections
a = 9.6452 (5) Åθ = 2.3–27.0°
b = 21.5350 (11) ŵ = 0.84 mm1
c = 13.5083 (7) ÅT = 110 K
β = 90.784 (1)°Prism, violet
V = 2805.5 (3) Å30.45 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3832 independent reflections
Radiation source: fine-focus sealed tube3667 reflections with I > 2σ(I)
graphiteRint = 0.016
[var phi] and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→12
Tmin = 0.818, Tmax = 1.000k = −26→26
6638 measured reflectionsl = −8→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064w = 1/[σ2(Fo2) + (0.0373P)2 + 0.1275P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3832 reflectionsΔρmax = 0.25 e Å3
410 parametersΔρmin = −0.21 e Å3
142 restraintsAbsolute structure: Flack (1983), 874 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.012 (9)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Ni10.50011 (3)0.399116 (12)0.49992 (3)0.01859 (8)
O10.58175 (16)0.44546 (8)0.37089 (12)0.0219 (4)
O20.66792 (16)0.46225 (7)0.51979 (12)0.0201 (3)
Cl10.6956 (5)0.2675 (2)0.1539 (3)0.0295 (7)0.554 (8)
O30.5575 (5)0.2886 (4)0.1347 (6)0.0444 (19)0.554 (8)
O40.7620 (5)0.3111 (2)0.2197 (4)0.0581 (17)0.554 (8)
O50.6945 (9)0.2080 (2)0.2001 (5)0.0439 (19)0.554 (8)
O60.7708 (7)0.2650 (3)0.0641 (4)0.070 (2)0.554 (8)
Cl1'0.6956 (6)0.2641 (3)0.1262 (4)0.0311 (10)0.446 (8)
O3'0.5794 (8)0.2974 (4)0.1623 (6)0.042 (2)0.446 (8)
O4'0.8213 (6)0.2957 (3)0.1496 (6)0.060 (3)0.446 (8)
O5'0.6992 (12)0.2028 (3)0.1656 (9)0.057 (3)0.446 (8)
O6'0.6838 (8)0.2577 (3)0.0218 (4)0.058 (2)0.446 (8)
O1W0.5173 (2)0.42855 (9)0.17034 (14)0.0296 (4)
H110.545 (3)0.4343 (13)0.2291 (11)0.044*
H120.537 (4)0.3925 (8)0.153 (2)0.044*
N10.3714 (2)0.46844 (10)0.56243 (16)0.0190 (4)
H10.423 (2)0.4982 (10)0.585 (2)0.023*
N20.4909 (2)0.35763 (9)0.63905 (16)0.0211 (4)
H20.428 (2)0.3296 (10)0.636 (2)0.025*
N30.6127 (2)0.32080 (10)0.44631 (17)0.0243 (4)
H30.652 (3)0.3351 (13)0.3944 (14)0.029*
N40.3296 (2)0.36063 (10)0.42555 (16)0.0242 (4)
H40.280 (3)0.3380 (12)0.4632 (19)0.029*
N50.7978 (2)0.57537 (11)0.53966 (18)0.0289 (5)
H510.739 (3)0.5514 (12)0.567 (2)0.035*
H520.814 (3)0.6115 (8)0.563 (2)0.035*
C10.3207 (3)0.44029 (12)0.65532 (18)0.0245 (5)
H1A0.24380.41120.64020.029*
H1B0.28520.47320.69950.029*
C20.4374 (3)0.40601 (11)0.70620 (19)0.0253 (5)
H2A0.51260.43540.72410.030*
H2B0.40370.38660.76780.030*
C30.6234 (3)0.33020 (13)0.6779 (2)0.0282 (6)
H3a0.69680.36290.67510.034*
C40.6109 (3)0.30893 (15)0.7856 (2)0.0378 (7)
H4A0.58140.34400.82650.057*
H4B0.70110.29370.80960.057*
H4C0.54230.27550.78950.057*
C50.6684 (3)0.27612 (12)0.6133 (2)0.0293 (6)
H5A0.58830.24770.60590.035*
H5B0.74180.25320.64990.035*
C60.7230 (3)0.28992 (12)0.5088 (2)0.0298 (6)
C70.8464 (3)0.33447 (13)0.5146 (2)0.0353 (7)
H7A0.88320.34090.44810.053*
H7B0.91880.31670.55750.053*
H7C0.81620.37430.54180.053*
C80.7727 (3)0.22831 (14)0.4626 (3)0.0393 (7)
H8A0.79210.23480.39230.059*
H8B0.70030.19670.46920.059*
H8C0.85730.21430.49690.059*
C90.5037 (3)0.27846 (12)0.4086 (2)0.0297 (6)
H9A0.46320.25510.46430.036*
H9B0.54440.24830.36200.036*
C100.3920 (3)0.31573 (13)0.3564 (2)0.0288 (6)
H10A0.43240.33830.29980.035*
H10B0.31940.28740.33040.035*
C110.2384 (3)0.40671 (11)0.37461 (19)0.0241 (5)
H11A0.29790.43280.33100.029*
C120.1271 (3)0.37581 (15)0.3090 (2)0.0335 (6)
H12A0.17190.35170.25680.050*
H12B0.06800.40780.27880.050*
H12C0.07040.34810.34940.050*
C130.1684 (2)0.45014 (12)0.44934 (19)0.0238 (5)
H13A0.12530.42400.50070.029*
H13B0.09230.47220.41420.029*
C140.2594 (2)0.49930 (12)0.50235 (18)0.0217 (5)
C150.3297 (3)0.54169 (12)0.42814 (19)0.0237 (5)
H15A0.38190.57400.46370.036*
H15B0.25920.56110.38530.036*
H15C0.39320.51730.38760.036*
C160.1671 (3)0.54025 (13)0.5675 (2)0.0259 (6)
H16A0.22560.56780.60790.039*
H16B0.11170.51380.61090.039*
H16C0.10530.56520.52530.039*
C170.6690 (2)0.47306 (11)0.42754 (19)0.0186 (5)
C180.7701 (2)0.51743 (11)0.38477 (18)0.0198 (5)
C190.8068 (2)0.51078 (12)0.28554 (19)0.0234 (5)
H190.76780.47770.24790.028*
C200.8984 (3)0.55104 (13)0.2407 (2)0.0292 (6)
H200.92470.54500.17390.035*
C210.9514 (3)0.60087 (12)0.2959 (2)0.0301 (6)
H211.01250.62960.26570.036*
C220.9161 (3)0.60871 (12)0.3934 (2)0.0276 (6)
H220.95320.64300.42920.033*
C230.8259 (2)0.56699 (12)0.4417 (2)0.0219 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.01972 (13)0.01555 (14)0.02064 (13)−0.00292 (12)0.00605 (9)−0.00109 (13)
O10.0225 (8)0.0217 (9)0.0217 (8)−0.0068 (7)0.0050 (7)−0.0017 (7)
O20.0227 (8)0.0171 (9)0.0207 (8)−0.0015 (6)0.0043 (7)−0.0002 (7)
Cl10.0273 (9)0.0245 (10)0.0371 (17)0.0031 (6)0.0107 (11)0.0046 (11)
O30.036 (2)0.035 (3)0.062 (4)0.005 (2)−0.007 (2)−0.016 (3)
O40.053 (3)0.045 (3)0.075 (4)−0.004 (2)−0.017 (3)−0.008 (2)
O50.055 (3)0.015 (2)0.062 (4)0.000 (2)0.014 (3)0.010 (2)
O60.071 (4)0.077 (4)0.065 (4)0.031 (3)0.052 (4)0.012 (3)
Cl1'0.0308 (12)0.0213 (12)0.041 (3)0.0025 (8)0.0045 (16)0.0042 (15)
O3'0.048 (4)0.033 (4)0.047 (4)0.016 (3)0.024 (3)0.001 (3)
O4'0.055 (3)0.038 (3)0.087 (6)−0.014 (3)−0.021 (3)0.020 (3)
O5'0.051 (4)0.027 (4)0.094 (7)0.008 (3)0.017 (5)0.010 (4)
O6'0.055 (4)0.079 (4)0.041 (3)0.016 (3)0.009 (3)−0.017 (3)
O1W0.0405 (11)0.0243 (10)0.0239 (9)0.0039 (8)−0.0026 (8)0.0000 (7)
N10.0222 (10)0.0145 (10)0.0205 (10)−0.0003 (8)0.0027 (8)0.0008 (8)
N20.0208 (10)0.0180 (10)0.0248 (10)0.0008 (8)0.0057 (8)0.0009 (8)
N30.0254 (10)0.0186 (11)0.0291 (11)−0.0042 (8)0.0107 (9)−0.0014 (9)
N40.0258 (10)0.0228 (11)0.0242 (10)−0.0061 (8)0.0086 (8)−0.0022 (9)
N50.0337 (12)0.0215 (11)0.0315 (12)−0.0095 (9)0.0063 (9)−0.0075 (9)
C10.0287 (12)0.0262 (13)0.0187 (11)0.0058 (10)0.0078 (10)0.0013 (10)
C20.0314 (13)0.0246 (13)0.0202 (11)0.0062 (10)0.0056 (10)0.0018 (10)
C30.0250 (12)0.0240 (14)0.0356 (15)0.0034 (10)0.0030 (11)0.0032 (11)
C40.0416 (16)0.0366 (16)0.0353 (15)0.0169 (13)0.0014 (13)0.0070 (13)
C50.0295 (13)0.0180 (12)0.0406 (15)0.0043 (10)0.0081 (11)0.0038 (11)
C60.0245 (13)0.0232 (14)0.0420 (16)0.0016 (10)0.0122 (11)−0.0024 (12)
C70.0229 (13)0.0326 (16)0.0507 (17)0.0009 (11)0.0090 (12)−0.0002 (13)
C80.0370 (16)0.0235 (15)0.058 (2)0.0074 (12)0.0127 (15)−0.0063 (14)
C90.0347 (13)0.0181 (13)0.0368 (14)−0.0057 (10)0.0146 (11)−0.0073 (11)
C100.0315 (14)0.0250 (14)0.0301 (14)−0.0081 (10)0.0079 (11)−0.0125 (11)
C110.0247 (12)0.0247 (13)0.0232 (12)−0.0063 (9)0.0049 (10)−0.0010 (10)
C120.0295 (13)0.0429 (17)0.0282 (13)−0.0081 (12)0.0010 (11)−0.0065 (12)
C130.0193 (11)0.0276 (13)0.0245 (12)−0.0013 (9)0.0031 (10)0.0017 (10)
C140.0229 (11)0.0224 (12)0.0200 (11)0.0015 (9)0.0040 (9)0.0031 (10)
C150.0278 (12)0.0222 (12)0.0212 (11)0.0021 (9)0.0048 (10)0.0034 (10)
C160.0263 (13)0.0259 (15)0.0256 (13)0.0059 (10)0.0062 (10)0.0040 (11)
C170.0197 (11)0.0140 (11)0.0222 (12)0.0024 (9)0.0045 (9)−0.0008 (9)
C180.0190 (11)0.0170 (12)0.0236 (12)0.0000 (8)0.0017 (9)0.0014 (9)
C190.0210 (12)0.0238 (13)0.0255 (12)−0.0011 (9)0.0037 (10)0.0014 (10)
C200.0253 (12)0.0355 (15)0.0269 (13)0.0006 (10)0.0083 (10)0.0080 (11)
C210.0210 (12)0.0288 (14)0.0405 (15)−0.0034 (9)0.0045 (11)0.0131 (12)
C220.0249 (12)0.0199 (13)0.0378 (15)−0.0048 (9)−0.0005 (11)0.0034 (11)
C230.0194 (11)0.0193 (12)0.0269 (12)0.0015 (9)0.0022 (10)0.0017 (10)

Geometric parameters (Å, °)

Ni1—N12.124 (2)C5—C61.541 (4)
Ni1—N22.084 (2)C5—H5A0.9900
Ni1—N32.138 (2)C5—H5B0.9900
Ni1—N42.087 (2)C6—C71.530 (4)
Ni1—O12.1659 (17)C6—C81.546 (4)
Ni1—O22.1280 (16)C7—H7A0.9800
O1—C171.276 (3)C7—H7B0.9800
O2—C171.268 (3)C7—H7C0.9800
Cl1—O61.423 (4)C8—H8A0.9800
Cl1—O51.425 (5)C8—H8B0.9800
Cl1—O31.427 (5)C8—H8C0.9800
Cl1—O41.437 (5)C9—C101.510 (4)
Cl1'—O6'1.421 (5)C9—H9A0.9900
Cl1'—O5'1.423 (6)C9—H9B0.9900
Cl1'—O3'1.422 (5)C10—H10A0.9900
Cl1'—O4'1.422 (6)C10—H10B0.9900
O1W—H110.843 (10)C11—C121.534 (4)
O1W—H120.833 (10)C11—C131.539 (3)
N1—C11.482 (3)C11—H11A1.0000
N1—C141.498 (3)C12—H12A0.9800
N1—H10.861 (10)C12—H12B0.9800
N2—C21.479 (3)C12—H12C0.9800
N2—C31.496 (3)C13—C141.545 (3)
N2—H20.858 (10)C13—H13A0.9900
N3—C91.477 (3)C13—H13B0.9900
N3—C61.504 (4)C14—C151.522 (3)
N3—H30.860 (10)C14—C161.538 (3)
N4—C101.478 (3)C15—H15A0.9800
N4—C111.489 (3)C15—H15B0.9800
N4—H40.86 (3)C15—H15C0.9800
N5—C231.366 (3)C16—H16A0.9800
N5—H510.86 (3)C16—H16B0.9800
N5—H520.854 (10)C16—H16C0.9800
C1—C21.504 (3)C17—C181.487 (3)
C1—H1A0.9900C18—C191.399 (3)
C1—H1B0.9900C18—C231.418 (3)
C2—H2A0.9900C19—C201.383 (3)
C2—H2B0.9900C19—H190.9500
C3—C51.522 (4)C20—C211.400 (4)
C3—C41.532 (4)C20—H200.9500
C3—H3a1.0000C21—C221.375 (4)
C4—H4A0.9800C21—H210.9500
C4—H4B0.9800C22—C231.416 (4)
C4—H4C0.9800C22—H220.9500
N2—Ni1—N4102.76 (8)N3—C6—C7107.2 (2)
N2—Ni1—N184.86 (8)N3—C6—C5110.60 (19)
N4—Ni1—N190.54 (8)C7—C6—C5110.5 (2)
N2—Ni1—O2101.64 (7)N3—C6—C8111.9 (2)
N4—Ni1—O2155.16 (8)C7—C6—C8108.2 (2)
N1—Ni1—O287.05 (7)C5—C6—C8108.4 (2)
N2—Ni1—N389.73 (8)C6—C7—H7A109.5
N4—Ni1—N385.66 (8)C6—C7—H7B109.5
N1—Ni1—N3172.56 (8)H7A—C7—H7B109.5
O2—Ni1—N399.07 (7)C6—C7—H7C109.5
N2—Ni1—O1160.67 (7)H7A—C7—H7C109.5
N4—Ni1—O195.07 (7)H7B—C7—H7C109.5
N1—Ni1—O1102.53 (7)C6—C8—H8A109.5
O2—Ni1—O161.50 (6)C6—C8—H8B109.5
N3—Ni1—O184.20 (7)H8A—C8—H8B109.5
C17—O1—Ni188.63 (14)C6—C8—H8C109.5
C17—O2—Ni190.56 (14)H8A—C8—H8C109.5
O6—Cl1—O5110.2 (4)H8B—C8—H8C109.5
O6—Cl1—O3110.1 (4)N3—C9—C10109.4 (2)
O5—Cl1—O3110.7 (4)N3—C9—H9A109.8
O6—Cl1—O4108.9 (4)C10—C9—H9A109.8
O5—Cl1—O4108.8 (4)N3—C9—H9B109.8
O3—Cl1—O4108.1 (4)C10—C9—H9B109.8
O6'—Cl1'—O5'106.4 (7)H9A—C9—H9B108.2
O6'—Cl1'—O3'109.6 (5)N4—C10—C9110.3 (2)
O5'—Cl1'—O3'110.8 (5)N4—C10—H10A109.6
O6'—Cl1'—O4'108.9 (5)C9—C10—H10A109.6
O5'—Cl1'—O4'110.2 (5)N4—C10—H10B109.6
O3'—Cl1'—O4'110.8 (5)C9—C10—H10B109.6
H11—O1W—H12109.4 (17)H10A—C10—H10B108.1
C1—N1—C14113.35 (19)N4—C11—C12112.5 (2)
C1—N1—Ni1104.50 (15)N4—C11—C13111.3 (2)
C14—N1—Ni1121.17 (16)C12—C11—C13109.5 (2)
C1—N1—H1101.7 (19)N4—C11—H11A107.8
C14—N1—H1105.3 (19)C12—C11—H11A107.8
Ni1—N1—H1109.1 (18)C13—C11—H11A107.8
C2—N2—C3111.5 (2)C11—C12—H12A109.5
C2—N2—Ni1105.70 (15)C11—C12—H12B109.5
C3—N2—Ni1116.01 (15)H12A—C12—H12B109.5
C2—N2—H2106 (2)C11—C12—H12C109.5
C3—N2—H2110 (2)H12A—C12—H12C109.5
Ni1—N2—H2107 (2)H12B—C12—H12C109.5
C9—N3—C6114.5 (2)C11—C13—C14117.97 (19)
C9—N3—Ni1103.96 (15)C11—C13—H13A107.8
C6—N3—Ni1121.14 (16)C14—C13—H13A107.8
C9—N3—H3105 (2)C11—C13—H13B107.8
C6—N3—H3107 (2)C14—C13—H13B107.8
Ni1—N3—H3103 (2)H13A—C13—H13B107.2
C10—N4—C11112.8 (2)N1—C14—C15107.37 (19)
C10—N4—Ni1103.81 (15)N1—C14—C16111.3 (2)
C11—N4—Ni1114.50 (15)C15—C14—C16107.4 (2)
C10—N4—H4104 (2)N1—C14—C13110.4 (2)
C11—N4—H4109 (2)C15—C14—C13111.2 (2)
Ni1—N4—H4113 (2)C16—C14—C13109.19 (19)
C23—N5—H51119 (2)C14—C15—H15A109.5
C23—N5—H52116 (2)C14—C15—H15B109.5
H51—N5—H52121 (3)H15A—C15—H15B109.5
N1—C1—C2109.5 (2)C14—C15—H15C109.5
N1—C1—H1A109.8H15A—C15—H15C109.5
C2—C1—H1A109.8H15B—C15—H15C109.5
N1—C1—H1B109.8C14—C16—H16A109.5
C2—C1—H1B109.8C14—C16—H16B109.5
H1A—C1—H1B108.2H16A—C16—H16B109.5
N2—C2—C1109.3 (2)C14—C16—H16C109.5
N2—C2—H2A109.8H16A—C16—H16C109.5
C1—C2—H2A109.8H16B—C16—H16C109.5
N2—C2—H2B109.8O2—C17—O1119.3 (2)
C1—C2—H2B109.8O2—C17—C18120.9 (2)
H2A—C2—H2B108.3O1—C17—C18119.8 (2)
N2—C3—C5110.5 (2)C19—C18—C23119.9 (2)
N2—C3—C4111.9 (2)C19—C18—C17118.9 (2)
C5—C3—C4110.0 (2)C23—C18—C17121.3 (2)
N2—C3—H3a108.1C20—C19—C18121.8 (2)
C5—C3—H3a108.1C20—C19—H19119.1
C4—C3—H3a108.1C18—C19—H19119.1
C3—C4—H4A109.5C19—C20—C21118.6 (2)
C3—C4—H4B109.5C19—C20—H20120.7
H4A—C4—H4B109.5C21—C20—H20120.7
C3—C4—H4C109.5C22—C21—C20120.7 (2)
H4A—C4—H4C109.5C22—C21—H21119.6
H4B—C4—H4C109.5C20—C21—H21119.6
C3—C5—C6118.7 (2)C21—C22—C23121.7 (3)
C3—C5—H5A107.6C21—C22—H22119.1
C6—C5—H5A107.6C23—C22—H22119.1
C3—C5—H5B107.6N5—C23—C18123.1 (2)
C6—C5—H5B107.6N5—C23—C22119.6 (2)
H5A—C5—H5B107.1C18—C23—C22117.3 (2)
N2—Ni1—O1—C17−31.3 (3)C2—N2—C3—C451.2 (3)
N4—Ni1—O1—C17171.28 (14)Ni1—N2—C3—C4172.23 (19)
N1—Ni1—O1—C1779.59 (14)N2—C3—C5—C671.2 (3)
O2—Ni1—O1—C170.00 (13)C4—C3—C5—C6−164.7 (2)
N3—Ni1—O1—C17−103.62 (14)C9—N3—C6—C7163.1 (2)
N2—Ni1—O2—C17169.89 (14)Ni1—N3—C6—C7−71.0 (2)
N4—Ni1—O2—C17−21.1 (2)C9—N3—C6—C5−76.4 (3)
N1—Ni1—O2—C17−105.97 (14)Ni1—N3—C6—C549.4 (3)
N3—Ni1—O2—C1778.28 (15)C9—N3—C6—C844.6 (3)
O1—Ni1—O2—C170.00 (13)Ni1—N3—C6—C8170.46 (18)
N2—Ni1—N1—C1−14.19 (16)C3—C5—C6—N3−61.6 (3)
N4—Ni1—N1—C188.57 (16)C3—C5—C6—C756.8 (3)
O2—Ni1—N1—C1−116.17 (16)C3—C5—C6—C8175.3 (2)
O1—Ni1—N1—C1−176.11 (15)C6—N3—C9—C10174.1 (2)
N2—Ni1—N1—C14−143.61 (18)Ni1—N3—C9—C1039.7 (2)
N4—Ni1—N1—C14−40.84 (18)C11—N4—C10—C9169.1 (2)
O2—Ni1—N1—C14114.42 (17)Ni1—N4—C10—C944.6 (2)
O1—Ni1—N1—C1454.48 (18)N3—C9—C10—N4−59.9 (3)
N4—Ni1—N2—C2−104.54 (16)C10—N4—C11—C1253.3 (3)
N1—Ni1—N2—C2−15.15 (16)Ni1—N4—C11—C12171.73 (16)
O2—Ni1—N2—C270.77 (16)C10—N4—C11—C13176.57 (19)
N3—Ni1—N2—C2169.98 (16)Ni1—N4—C11—C13−65.0 (2)
O1—Ni1—N2—C298.6 (2)N4—C11—C13—C1471.8 (3)
N4—Ni1—N2—C3131.31 (17)C12—C11—C13—C14−163.2 (2)
N1—Ni1—N2—C3−139.30 (18)C1—N1—C14—C15163.3 (2)
O2—Ni1—N2—C3−53.38 (18)Ni1—N1—C14—C15−71.2 (2)
N3—Ni1—N2—C345.83 (18)C1—N1—C14—C1646.1 (3)
O1—Ni1—N2—C3−25.6 (3)Ni1—N1—C14—C16171.49 (16)
N2—Ni1—N3—C990.51 (16)C1—N1—C14—C13−75.4 (2)
N4—Ni1—N3—C9−12.31 (16)Ni1—N1—C14—C1350.1 (2)
O2—Ni1—N3—C9−167.74 (16)C11—C13—C14—N1−61.3 (3)
O1—Ni1—N3—C9−107.87 (16)C11—C13—C14—C1557.7 (3)
N2—Ni1—N3—C6−40.04 (18)C11—C13—C14—C16176.0 (2)
N4—Ni1—N3—C6−142.86 (18)Ni1—O2—C17—O10.0 (2)
O2—Ni1—N3—C661.70 (18)Ni1—O2—C17—C18179.87 (19)
O1—Ni1—N3—C6121.58 (18)Ni1—O1—C17—O20.0 (2)
N2—Ni1—N4—C10−105.88 (17)Ni1—O1—C17—C18−179.88 (19)
N1—Ni1—N4—C10169.26 (17)O2—C17—C18—C19155.0 (2)
O2—Ni1—N4—C1085.1 (2)O1—C17—C18—C19−25.2 (3)
N3—Ni1—N4—C10−17.14 (17)O2—C17—C18—C23−26.9 (3)
O1—Ni1—N4—C1066.63 (17)O1—C17—C18—C23152.9 (2)
N2—Ni1—N4—C11130.71 (15)C23—C18—C19—C200.8 (4)
N1—Ni1—N4—C1145.86 (16)C17—C18—C19—C20178.9 (2)
O2—Ni1—N4—C11−38.3 (3)C18—C19—C20—C21−2.2 (4)
N3—Ni1—N4—C11−140.55 (16)C19—C20—C21—C221.7 (4)
O1—Ni1—N4—C11−56.77 (16)C20—C21—C22—C230.3 (4)
C14—N1—C1—C2175.3 (2)C19—C18—C23—N5−178.1 (2)
Ni1—N1—C1—C241.4 (2)C17—C18—C23—N53.8 (4)
C3—N2—C2—C1169.3 (2)C19—C18—C23—C221.1 (3)
Ni1—N2—C2—C142.4 (2)C17—C18—C23—C22−176.9 (2)
N1—C1—C2—N2−58.6 (3)C21—C22—C23—N5177.6 (2)
C2—N2—C3—C5174.1 (2)C21—C22—C23—C18−1.7 (4)
Ni1—N2—C3—C5−64.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1wi0.86 (2)2.15 (2)2.995 (3)166 (2)
N2—H2···O5ii0.86 (2)2.56 (2)3.304 (8)147 (2)
N2—H2···O5'ii0.86 (2)2.35 (2)3.125 (11)150 (3)
N3—H3···O10.86 (2)2.49 (3)2.885 (3)109 (2)
N4—H4···O6ii0.86 (3)2.61 (2)3.343 (6)145 (3)
N4—H4···O6'ii0.86 (3)2.40 (2)3.195 (6)155 (3)
N5—H51···O20.85 (3)2.13 (3)2.751 (3)129 (2)
N5—H52···O4'i0.85 (1)2.32 (1)3.155 (6)168 (3)
O1w—H11···O10.84 (2)1.96 (2)2.795 (2)172 (3)
O1w—H12···O30.83 (2)2.26 (2)3.077 (9)167 (3)
O1w—H12···O3'0.83 (2)2.09 (2)2.890 (9)160 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5028).

References

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  • Ou, G.-C., Zhang, M., Yuan, X.-Y. & Dai, Y.-Q. (2008b). Acta Cryst. E64, m1588. [PMC free article] [PubMed]
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