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The title compound, [Ni(C16H28N2O8)], is isostructural with its CuII and CoII analogues. The NiII atom lies on a centre of inversion and exhibits a distorted octa­hedral coordination environment involving two carboxyl­ate O atoms, two ether O atoms and two amino N atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042103/bi2080sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042103/bi2080Isup2.hkl
Contains datablock I

CCDC reference: 627328

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.067
  • Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O2 .. 6.09 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 1999); software used to prepare material for publication: X-SEED.

(1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-7,16-diacetato)nickel(II) top
Crystal data top
[Ni(C16H28N2O8)]Z = 1
Mr = 435.11F(000) = 230
Triclinic, P1Dx = 1.652 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9320 (2) ÅCell parameters from 237 reflections
b = 7.4993 (2) Åθ = 3.1–30.7°
c = 9.0751 (2) ŵ = 1.16 mm1
α = 80.522 (2)°T = 123 K
β = 70.068 (2)°Block, pale blue
γ = 87.206 (2)°0.25 × 0.20 × 0.15 mm
V = 437.44 (2) Å3
Data collection top
Bruker X8 APEX-II CCD
diffractometer
2619 independent reflections
Radiation source: fine-focus sealed tube2458 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 30.7°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 99
Tmin = 0.774, Tmax = 0.840k = 1010
5085 measured reflectionsl = 1113
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.026P)2 + 0.241P]
where P = (Fo2 + 2Fc2)/3
2619 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.47 e Å3
Special details top

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) top
xyzUiso*/Ueq
Ni10.50000.00000.00000.01098 (7)
O10.45496 (15)0.23545 (13)0.42830 (11)0.01321 (19)
N10.55857 (17)0.10629 (15)0.17969 (13)0.0109 (2)
C10.3298 (2)0.37276 (18)0.41596 (16)0.0140 (2)
H1B0.24170.42560.52410.017*
H1A0.41950.46990.36850.017*
O20.68716 (15)0.26407 (13)0.15170 (11)0.01366 (19)
C20.6444 (2)0.20278 (18)0.29875 (16)0.0132 (2)
H2B0.63380.24810.20530.016*
H2A0.75640.26880.32830.016*
O30.23856 (15)0.13588 (13)0.07362 (11)0.01399 (19)
C30.6936 (2)0.00315 (18)0.25711 (15)0.0128 (2)
H3A0.68270.04390.35530.015*
H3B0.83770.01360.18510.015*
O40.04772 (16)0.27894 (14)0.27123 (13)0.0182 (2)
C40.6568 (2)0.28830 (17)0.11111 (16)0.0135 (2)
H4B0.72940.32140.17980.016*
H4A0.54900.37940.10920.016*
C50.8062 (2)0.29173 (19)0.05406 (16)0.0144 (2)
H5A0.87930.40950.09300.017*
H5B0.90870.19460.05610.017*
C60.8052 (2)0.30931 (19)0.31836 (16)0.0148 (2)
H6B0.88260.20180.35630.018*
H6A0.90580.40570.33290.018*
C70.3525 (2)0.13618 (18)0.29396 (15)0.0124 (2)
H7A0.36130.23220.35430.015*
H7B0.30400.02380.37040.015*
C80.1990 (2)0.19141 (17)0.20721 (15)0.0124 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01130 (12)0.01351 (12)0.01031 (11)0.00252 (8)0.00522 (8)0.00522 (8)
O10.0142 (4)0.0144 (4)0.0109 (4)0.0015 (3)0.0034 (3)0.0032 (3)
N10.0111 (5)0.0118 (5)0.0105 (5)0.0001 (4)0.0044 (4)0.0021 (4)
C10.0162 (6)0.0129 (6)0.0121 (6)0.0012 (5)0.0040 (5)0.0012 (4)
O20.0134 (4)0.0178 (5)0.0109 (4)0.0037 (3)0.0052 (3)0.0019 (3)
C20.0122 (6)0.0148 (6)0.0124 (6)0.0008 (4)0.0045 (5)0.0013 (4)
O30.0131 (4)0.0182 (5)0.0128 (4)0.0034 (3)0.0061 (3)0.0059 (4)
C30.0134 (6)0.0149 (6)0.0119 (5)0.0002 (4)0.0067 (5)0.0017 (4)
O40.0141 (5)0.0210 (5)0.0211 (5)0.0048 (4)0.0055 (4)0.0099 (4)
C40.0162 (6)0.0118 (5)0.0138 (6)0.0020 (4)0.0060 (5)0.0029 (4)
C50.0141 (6)0.0165 (6)0.0142 (6)0.0032 (5)0.0075 (5)0.0002 (5)
C60.0135 (6)0.0171 (6)0.0124 (6)0.0025 (5)0.0026 (5)0.0018 (5)
C70.0135 (6)0.0140 (6)0.0103 (5)0.0013 (4)0.0038 (4)0.0044 (4)
C80.0139 (6)0.0110 (5)0.0124 (6)0.0014 (4)0.0044 (5)0.0014 (4)
Geometric parameters (Å, º) top
Ni1—N12.0906 (11)C2—H2B0.990
Ni1—O22.3738 (9)C2—H2A0.990
Ni1—O31.9970 (10)O3—C81.2834 (16)
Ni1—N1i2.0906 (11)C3—H3A0.990
Ni1—O2i2.3738 (9)C3—H3B0.990
Ni1—O3i1.9970 (10)O4—C81.2294 (17)
O1—C11.4203 (16)C4—C51.5005 (19)
O1—C21.4321 (16)C4—H4B0.990
N1—C71.4840 (17)C4—H4A0.990
N1—C31.4924 (17)C5—H5A0.990
N1—C41.4953 (16)C5—H5B0.990
C1—C6i1.507 (2)C6—C1i1.507 (2)
C1—H1B0.990C6—H6B0.990
C1—H1A0.990C6—H6A0.990
O2—C51.4441 (16)C7—C81.5308 (19)
O2—C61.4446 (16)C7—H7A0.990
C2—C31.5086 (18)C7—H7B0.990
N1—Ni1—O280.35 (4)H2B—C2—H2A108.1
N1i—Ni1—O299.65 (4)C8—O3—Ni1115.88 (9)
N1—Ni1—O382.26 (4)N1—C3—C2114.54 (11)
O2—Ni1—O392.79 (4)N1—C3—H3A108.6
O3i—Ni1—N197.74 (4)C2—C3—H3A108.6
O3i—Ni1—O287.21 (4)N1—C3—H3B108.6
O3—Ni1—O3i180.0C2—C3—H3B108.6
O3—Ni1—N1i97.74 (4)H3A—C3—H3B107.6
O3i—Ni1—N1i82.26 (4)N1—C4—C5111.87 (10)
N1i—Ni1—N1180.0N1—C4—H4B109.2
O3—Ni1—O2i87.21 (4)C5—C4—H4B109.2
O3i—Ni1—O2i92.79 (4)N1—C4—H4A109.2
N1i—Ni1—O2i80.35 (4)C5—C4—H4A109.2
N1—Ni1—O2i99.65 (4)H4B—C4—H4A107.9
O2—Ni1—O2i180.00 (3)O2—C5—C4106.42 (11)
C1—O1—C2114.52 (10)O2—C5—H5A110.4
C7—N1—C3112.60 (10)C4—C5—H5A110.4
C7—N1—C4106.93 (10)O2—C5—H5B110.4
C3—N1—C4107.70 (10)C4—C5—H5B110.4
C7—N1—Ni1104.64 (8)H5A—C5—H5B108.6
C3—N1—Ni1116.28 (8)O2—C6—C1i111.73 (11)
C4—N1—Ni1108.28 (8)O2—C6—H6B109.3
O1—C1—C6i114.50 (11)C1i—C6—H6B109.3
O1—C1—H1B108.6O2—C6—H6A109.3
C6i—C1—H1B108.6C1i—C6—H6A109.3
O1—C1—H1A108.6H6B—C6—H6A107.9
C6i—C1—H1A108.6N1—C7—C8110.75 (10)
H1B—C1—H1A107.6N1—C7—H7A109.5
C5—O2—C6111.15 (10)C8—C7—H7A109.5
C5—O2—Ni1100.10 (7)N1—C7—H7B109.5
C6—O2—Ni1131.97 (8)C8—C7—H7B109.5
O1—C2—C3110.25 (11)H7A—C7—H7B108.1
O1—C2—H2B109.6O4—C8—O3125.59 (13)
C3—C2—H2B109.6O4—C8—C7118.58 (12)
O1—C2—H2A109.6O3—C8—C7115.80 (11)
C3—C2—H2A109.6
Symmetry code: (i) x+1, y, z.
 

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