(1,4,10,13-Tetra­oxa-7,16-diaza­cyclo­octa­decane-7,16-diacetato)cobalt(II)

The title compound, [Co(C₁₆H₂₈N₂O₈)], is isostructural with its Cu^II and Ni^II analogues. The Co^II 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.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.025
• wR factor = 0.058
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O3      ..       5.19 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   N1      ..       5.53 su
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.18 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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)cobalt(II)

Crystal data

[Co(C16H28N2O8)]	Z = 1
Mr = 435.33	F(000) = 229
Triclinic, P1	Dx = 1.656 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8973 (5) Å	Cell parameters from 249 reflections
b = 7.5264 (5) Å	θ = 2.4–28.4°
c = 9.1052 (7) Å	µ = 1.03 mm^−1
α = 79.851 (2)°	T = 123 K
β = 69.746 (2)°	Block, pale purple
γ = 86.440 (2)°	0.25 × 0.25 × 0.20 mm
V = 436.50 (5) Å^3

Data collection

Bruker X8 APEX-II CCD diffractometer	2177 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 28.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→9
Tmin = 0.700, Tmax = 0.813	k = −10→10
4881 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0182P)^2 + 0.3282P] where P = (Fo^2 + 2Fc^2)/3
2177 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.5000	0.0000	0.0000	0.01016 (7)
O1	0.45386 (15)	−0.23261 (12)	0.42526 (11)	0.01266 (19)
N1	0.55978 (17)	0.11021 (14)	0.18156 (13)	0.0099 (2)
C1	0.3334 (2)	−0.37202 (17)	0.41396 (16)	0.0132 (3)
H1B	0.2460	−0.4262	0.5223	0.016*
H1A	0.4272	−0.4674	0.3663	0.016*
O2	0.68587 (15)	0.26844 (13)	−0.15063 (11)	0.01311 (19)
C2	0.6458 (2)	−0.19912 (17)	0.29804 (15)	0.0124 (2)
H2A	0.6380	−0.2413	0.2032	0.015*
H2B	0.7575	−0.2669	0.3285	0.015*
O3	0.23440 (15)	0.13282 (13)	0.07986 (11)	0.01356 (19)
C3	0.6940 (2)	−0.00040 (17)	0.25936 (15)	0.0116 (2)
H3B	0.6799	0.0439	0.3587	0.014*
H3A	0.8397	0.0170	0.1887	0.014*
O4	0.04622 (15)	0.28279 (14)	0.27196 (12)	0.0175 (2)
C4	0.6585 (2)	0.29051 (17)	0.11065 (15)	0.0122 (2)
H4A	0.7329	0.3228	0.1777	0.015*
H4B	0.5498	0.3825	0.1091	0.015*
C5	0.8067 (2)	0.29279 (18)	−0.05469 (16)	0.0131 (3)
H5B	0.8814	0.4092	−0.0948	0.016*
H5A	0.9091	0.1942	−0.0570	0.016*
C7	0.3527 (2)	0.14072 (17)	0.29532 (15)	0.0115 (2)
H7B	0.3606	0.2378	0.3536	0.014*
H7A	0.3054	0.0293	0.3736	0.014*
C8	0.1975 (2)	0.19353 (17)	0.20988 (15)	0.0116 (2)
C9	0.8035 (2)	0.31109 (18)	−0.31712 (15)	0.0139 (3)
H9A	0.8824	0.2032	−0.3533	0.017*
H9B	0.9038	0.4078	−0.3341	0.017*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.00940 (13)	0.01182 (12)	0.01142 (12)	0.00237 (9)	−0.00522 (9)	−0.00485 (9)
O1	0.0128 (5)	0.0131 (4)	0.0120 (4)	−0.0019 (3)	−0.0035 (4)	−0.0027 (3)
N1	0.0099 (5)	0.0093 (5)	0.0107 (5)	0.0001 (4)	−0.0041 (4)	−0.0009 (4)
C1	0.0157 (6)	0.0106 (6)	0.0128 (6)	−0.0023 (5)	−0.0046 (5)	−0.0004 (5)
O2	0.0122 (5)	0.0164 (4)	0.0114 (4)	−0.0034 (4)	−0.0049 (4)	−0.0010 (3)
C2	0.0109 (6)	0.0125 (6)	0.0132 (6)	0.0011 (5)	−0.0042 (5)	−0.0008 (5)
O3	0.0115 (5)	0.0168 (5)	0.0147 (5)	0.0028 (4)	−0.0064 (4)	−0.0055 (4)
C3	0.0111 (6)	0.0124 (6)	0.0132 (6)	0.0003 (5)	−0.0071 (5)	−0.0011 (4)
O4	0.0128 (5)	0.0187 (5)	0.0227 (5)	0.0047 (4)	−0.0062 (4)	−0.0091 (4)
C4	0.0146 (6)	0.0092 (5)	0.0140 (6)	−0.0016 (5)	−0.0066 (5)	−0.0015 (4)
C5	0.0123 (6)	0.0140 (6)	0.0146 (6)	−0.0027 (5)	−0.0071 (5)	−0.0007 (5)
C7	0.0109 (6)	0.0125 (6)	0.0111 (6)	0.0016 (5)	−0.0031 (5)	−0.0041 (4)
C8	0.0107 (6)	0.0094 (5)	0.0144 (6)	−0.0012 (4)	−0.0041 (5)	−0.0017 (4)
C9	0.0121 (6)	0.0160 (6)	0.0126 (6)	−0.0028 (5)	−0.0028 (5)	−0.0014 (5)

Geometric parameters (Å, º)

Co1—N1	2.1421 (11)	C2—H2A	0.990
Co1—O2	2.3946 (9)	C2—H2B	0.990
Co1—O3	1.9976 (10)	O3—C8	1.2816 (16)
Co1—N1^i	2.1421 (11)	C3—H3B	0.990
Co1—O2^i	2.3946 (9)	C3—H3A	0.990
Co1—O3^i	1.9976 (10)	O4—C8	1.2241 (16)
O1—C1	1.4168 (15)	C4—C5	1.4965 (18)
O1—C2	1.4264 (16)	C4—H4A	0.990
N1—C7	1.4781 (16)	C4—H4B	0.990
N1—C3	1.4842 (16)	C5—H5B	0.990
N1—C4	1.4911 (16)	C5—H5A	0.990
C1—C9^i	1.5032 (19)	C7—C8	1.5241 (18)
C1—H1B	0.990	C7—H7B	0.990
C1—H1A	0.990	C7—H7A	0.990
O2—C9	1.4383 (15)	C9—C1^i	1.5032 (19)
O2—C5	1.4389 (15)	C9—H9A	0.990
C2—C3	1.5056 (17)	C9—H9B	0.990
N1—Co1—O2	78.98 (4)	H2A—C2—H2B	108.2
N1—Co1—O2^i	101.02 (4)	C8—O3—Co1	117.15 (8)
N1—Co1—O3	81.13 (4)	N1—C3—C2	114.05 (10)
O2—Co1—O3	93.19 (4)	N1—C3—H3B	108.7
O3—Co1—N1^i	98.87 (4)	C2—C3—H3B	108.7
O3—Co1—O2^i	86.81 (4)	N1—C3—H3A	108.7
O3^i—Co1—O3	180.00 (6)	C2—C3—H3A	108.7
O3^i—Co1—N1^i	81.13 (4)	H3B—C3—H3A	107.6
O3^i—Co1—N1	98.87 (4)	N1—C4—C5	111.91 (10)
N1^i—Co1—N1	180.00 (8)	N1—C4—H4A	109.2
O3^i—Co1—O2^i	93.19 (4)	C5—C4—H4A	109.2
N1^i—Co1—O2^i	78.98 (4)	N1—C4—H4B	109.2
O3^i—Co1—O2	86.81 (4)	C5—C4—H4B	109.2
N1^i—Co1—O2	101.02 (4)	H4A—C4—H4B	107.9
O2^i—Co1—O2	180.00 (6)	O2—C5—C4	106.70 (11)
C1—O1—C2	114.84 (10)	O2—C5—H5B	110.4
C7—N1—C3	112.37 (10)	C4—C5—H5B	110.4
C7—N1—C4	107.30 (10)	O2—C5—H5A	110.4
C3—N1—C4	108.16 (10)	C4—C5—H5A	110.4
C7—N1—Co1	104.54 (7)	H5B—C5—H5A	108.6
C3—N1—Co1	115.74 (8)	N1—C7—C8	110.96 (10)
C4—N1—Co1	108.38 (8)	N1—C7—H7B	109.4
O1—C1—C9^i	114.23 (11)	C8—C7—H7B	109.4
O1—C1—H1B	108.7	N1—C7—H7A	109.4
C9^i—C1—H1B	108.7	C8—C7—H7A	109.4
O1—C1—H1A	108.7	H7B—C7—H7A	108.0
C9^i—C1—H1A	108.7	O4—C8—O3	125.43 (13)
H1B—C1—H1A	107.6	O4—C8—C7	118.59 (12)
C9—O2—C5	111.39 (10)	O3—C8—C7	115.91 (11)
C9—O2—Co1	130.14 (8)	O2—C9—C1^i	111.64 (11)
C5—O2—Co1	100.34 (7)	O2—C9—H9A	109.3
O1—C2—C3	110.10 (10)	C1^i—C9—H9A	109.3
O1—C2—H2A	109.6	O2—C9—H9B	109.3
C3—C2—H2A	109.6	C1^i—C9—H9B	109.3
O1—C2—H2B	109.6	H9A—C9—H9B	108.0
C3—C2—H2B	109.6

Symmetry code: (i) −x+1, −y, −z.