Bis­(triethanolamine)­cobalt(II) benzene-1,4-dioxy­di­acetate

The title complex, [Co(C₆H₁₅NO₃)₂](C₁₀H₈O₆), comprises a Co^II cation, coordinated centrosymmetrically in an octahedral N₂O₄ mode by two tridentate triethanolamine ligands, and a centrosymmetric benzene-1,4-dioxy­acetate dianion. The ions are linked by hydrogen bonds into a supramolecular network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.056
• wR factor = 0.165
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT410_ALERT_2_A Short Intra H...H Contact  H2'1   ..  H6B     ..       1.65 Ang.

Author Response: ... arising from the interactions between disorder carbon atoms.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.19
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C6
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C5
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H8 O6

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(triethanolamine)cobalt(II) benzene-1,4-dioxydiacetate

Crystal data

[Co(C6H15NO3)2](C10H8O6)	F(000) = 614
Mr = 581.47	Dx = 1.463 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5364 reflections
a = 11.116 (2) Å	θ = 3.1–27.4°
b = 10.480 (2) Å	µ = 0.72 mm^−1
c = 11.369 (2) Å	T = 293 K
β = 94.88 (3)°	Block, pink
V = 1319.7 (4) Å^3	0.38 × 0.27 × 0.18 mm
Z = 2

Data collection

Rigaku RAXIS-RAPID diffractometer	3013 independent reflections
Radiation source: fine-focus sealed tube	1996 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.773, Tmax = 0.882	l = −14→14
5772 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.1059P)^2] where P = (Fo^2 + 2Fc^2)/3
3013 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 1.05 e Å^−3
6 restraints	Δρmin = −0.48 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.5000	0.5000	0.5000	0.0322 (2)
N1	0.4123 (2)	0.3220 (3)	0.4449 (2)	0.0381 (7)
O1	0.6213 (2)	0.4428 (2)	0.3822 (2)	0.0394 (6)
O2	0.3765 (2)	0.5702 (2)	0.3650 (2)	0.0416 (6)
O3	0.3526 (4)	0.0319 (5)	0.6141 (5)	0.112 (2)
O4	0.1466 (3)	−0.0695 (3)	0.6931 (2)	0.0612 (8)
O5	−0.0443 (2)	−0.1339 (3)	0.6648 (2)	0.0570 (8)
O6	−0.0020 (2)	−0.2408 (3)	0.4505 (2)	0.0475 (7)
C1	0.603 (1)	0.3082 (9)	0.364 (2)	0.046 (3)	0.50
C2	0.4719 (7)	0.2737 (8)	0.3408 (6)	0.046 (1)	0.50
C3	0.284 (1)	0.479 (1)	0.326 (3)	0.048 (4)	0.50
C4	0.2824 (6)	0.3658 (8)	0.4081 (7)	0.047 (1)	0.50
C5	0.3273 (5)	0.1149 (5)	0.5209 (4)	0.070 (1)
C6	0.3935 (6)	0.2392 (5)	0.5429 (4)	0.078 (2)
C7	0.0592 (3)	−0.1194 (4)	0.6342 (3)	0.0418 (8)
C8	0.0857 (4)	−0.1617 (4)	0.5105 (3)	0.0463 (9)
C9	0.0021 (3)	−0.3693 (4)	0.4787 (3)	0.0383 (8)
C10	−0.0568 (3)	−0.4507 (4)	0.3979 (3)	0.0421 (8)
C11	−0.0591 (3)	−0.5815 (4)	0.4183 (3)	0.0412 (8)
C1'	0.601 (1)	0.3180 (9)	0.332 (2)	0.046 (3)	0.50
C2'	0.5214 (7)	0.2461 (7)	0.4093 (7)	0.046 (1)	0.50
C3'	0.276 (1)	0.483 (1)	0.349 (3)	0.048 (4)	0.50
C4'	0.3241 (6)	0.3491 (8)	0.3436 (6)	0.047 (1)	0.50
H1	0.6769	0.4941	0.3478	0.047*
H2	0.3807	0.6520	0.3339	0.050*
H3	0.2941	0.0275	0.6534	0.134*
H10	−0.0955	−0.4178	0.3288	0.051*
H11	−0.0988	−0.6356	0.3630	0.049*
H1'1	0.6771	0.2736	0.3277	0.055*	0.50
H1'2	0.5619	0.3251	0.2522	0.055*	0.50
H2'1	0.5696	0.2199	0.4804	0.055*	0.50
H2'2	0.4925	0.1694	0.3683	0.055*	0.50
H3'1	0.2276	0.5033	0.2761	0.058*	0.50
H3'2	0.2255	0.4913	0.4138	0.058*	0.50
H4'1	0.2576	0.2892	0.3435	0.056*	0.50
H4'2	0.3624	0.3377	0.2707	0.056*	0.50
H1A	0.6369	0.2625	0.4333	0.055*	0.50
H1B	0.6460	0.2812	0.2975	0.055*	0.50
H2A	0.4374	0.3137	0.2687	0.055*	0.50
H2B	0.4623	0.1819	0.3333	0.055*	0.50
H3A	0.2995	0.4488	0.2474	0.058*	0.50
H3B	0.2064	0.5203	0.3201	0.058*	0.50
H4A	0.2373	0.2964	0.3690	0.056*	0.50
H4B	0.2427	0.3896	0.4776	0.056*	0.50
H5A	0.2411	0.1309	0.5108	0.084*
H5B	0.3511	0.0765	0.4488	0.084*
H6A	0.3502	0.2878	0.5984	0.094*
H6B	0.4722	0.2194	0.5821	0.094*
H8A	0.0952	−0.0861	0.4630	0.056*
H8B	0.1622	−0.2067	0.5164	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0370 (3)	0.0345 (4)	0.0253 (3)	−0.0001 (3)	0.0046 (2)	−0.0007 (3)
N1	0.045 (2)	0.041 (2)	0.029 (1)	−0.006 (1)	0.005 (1)	0.000 (1)
O1	0.040 (1)	0.045 (1)	0.035 (1)	−0.004 (1)	0.009 (1)	−0.000 (1)
O2	0.050 (1)	0.039 (2)	0.036 (1)	−0.002 (1)	0.004 (1)	0.005 (1)
O3	0.094 (3)	0.116 (4)	0.122 (4)	−0.036 (3)	−0.016 (3)	0.054 (3)
O4	0.070 (2)	0.074 (2)	0.042 (2)	−0.023 (2)	0.017 (1)	−0.016 (2)
O5	0.052 (2)	0.079 (2)	0.041 (2)	0.003 (1)	0.007 (1)	−0.016 (1)
O6	0.065 (2)	0.043 (2)	0.034 (1)	0.006 (1)	−0.004 (1)	−0.001 (1)
C1	0.050 (2)	0.046 (3)	0.04 (1)	0.004 (2)	0.010 (4)	−0.012 (4)
C2	0.056 (4)	0.042 (3)	0.040 (3)	−0.004 (3)	0.009 (3)	−0.009 (3)
C3	0.035 (2)	0.057 (3)	0.052 (9)	−0.001 (2)	0.003 (4)	0.000 (3)
C4	0.044 (3)	0.057 (3)	0.039 (3)	−0.010 (3)	0.002 (2)	0.002 (3)
C5	0.084 (3)	0.062 (3)	0.066 (3)	−0.023 (3)	0.012 (2)	0.020 (2)
C6	0.116 (4)	0.077 (4)	0.040 (2)	−0.052 (3)	−0.007 (2)	0.012 (2)
C7	0.060 (2)	0.035 (2)	0.031 (2)	0.003 (2)	0.007 (2)	0.002 (2)
C8	0.062 (2)	0.044 (2)	0.033 (2)	0.000 (2)	0.006 (2)	−0.002 (2)
C9	0.044 (2)	0.043 (2)	0.029 (2)	0.008 (2)	0.008 (2)	0.001 (1)
C10	0.050 (2)	0.049 (2)	0.027 (2)	0.007 (2)	−0.003 (2)	−0.002 (2)
C11	0.046 (2)	0.045 (2)	0.032 (2)	0.002 (2)	−0.002 (2)	−0.006 (2)
C1'	0.050 (2)	0.046 (3)	0.04 (1)	0.004 (2)	0.010 (4)	−0.012 (4)
C2'	0.056 (4)	0.042 (3)	0.040 (3)	−0.004 (3)	0.009 (3)	−0.009 (3)
C3'	0.035 (2)	0.057 (3)	0.052 (9)	−0.001 (2)	0.003 (4)	0.000 (3)
C4'	0.044 (3)	0.057 (3)	0.039 (3)	−0.010 (3)	0.002 (2)	0.002 (3)

Geometric parameters (Å, º)

Co1—O1	2.068 (2)	C3—H3A	0.9700
Co1—O2	2.103 (2)	C3—H3B	0.9700
Co1—N1	2.172 (3)	C4—H4A	0.9700
Co1—O1^i	2.068 (2)	C4—H4B	0.9700
Co1—O2^i	2.103 (2)	C5—C6	1.507 (7)
Co1—N1^i	2.172 (3)	C5—H5A	0.9700
N1—C2	1.494 (7)	C5—H5B	0.9700
N1—C4	1.538 (7)	C6—H6A	0.9700
N1—C6	1.441 (5)	C6—H6B	0.9700
N1—C2'	1.533 (7)	C7—C8	1.527 (5)
N1—C4'	1.475 (7)	C8—H8A	0.9700
O1—C1	1.437 (8)	C8—H8B	0.9700
O1—C1'	1.439 (8)	C9—C10	1.378 (5)
O1—H1	0.9300	C9—C11^ii	1.383 (5)
O2—C3'	1.441 (8)	C10—C11	1.391 (6)
O2—C3	1.443 (8)	C10—H10	0.9300
O2—H2	0.9300	C11—C9^ii	1.383 (5)
O3—C5	1.382 (6)	C11—H11	0.9300
O3—H3	0.8200	C1'—C2'	1.51 (1)
O4—C7	1.247 (5)	C1'—H1'1	0.9700
O5—C7	1.239 (4)	C1'—H1'2	0.9700
O6—C8	1.411 (5)	C2'—H2'1	0.9700
O6—C9	1.384 (5)	C2'—H2'2	0.9700
C1—C2	1.50 (1)	C3'—H3'1	0.9700
C1—H1A	0.9700	C3'—H3'2	0.9700
C1—H1B	0.9700	C3'—C4'	1.51 (2)
C2—H2A	0.9700	C4'—H4'1	0.9700
C2—H2B	0.9700	C4'—H4'2	0.9700
C3—C4	1.51 (2)
O1—Co1—O1^i	180	C3—O2—Co1	113.3 (5)
O1—Co1—O2	92.87 (9)	C3—O2—H2	123.4
O1—Co1—O2^i	87.13 (9)	C3—C4—N1	109.7 (8)
O1—Co1—N1	82.3 (1)	C3—C4—H4A	109.7
O1—Co1—N1^i	97.7 (1)	C3—C4—H4B	109.7
O1—Co1—O2^i	87.13 (9)	C4—N1—Co1	102.1 (4)
O1^i—Co1—O2^i	92.87 (9)	C4—C3—H3A	109.2
O1^i—Co1—N1^i	82.3 (1)	C4—C3—H3B	109.2
O1^i—Co1—N1	97.7 (1)	C5—O3—H3	109.5
O1—C1—C2	113 (1)	C5—C6—H6A	107.4
O1—C1—H1A	109.1	C5—C6—H6B	107.4
O1—C1—H1B	109.1	C6—N1—Co1	112.6 (2)
O1—C1'—C2'	107.5 (8)	C6—N1—C2	120.8 (5)
O1—C1'—H1'1	110.2	C6—N1—C4	101.2 (4)
O1—C1'—H1'2	110.2	C6—N1—C2'	93.5 (5)
O2—Co1—O2^i	180	C6—N1—C4'	126.1 (4)
O2—Co1—N1^i	99.2 (1)	C6—C5—H5A	109.5
O2^i—Co1—N1^i	80.8 (1)	C6—C5—H5B	109.5
O2—Co1—N1	80.8 (1)	C7—C8—H8A	108.3
O2^i—Co1—N1	99.2 (1)	C7—C8—H8B	108.3
O2—C3—C4	112 (1)	C9—O6—C8	116.8 (3)
O2—C3—H3A	109.2	C9—C10—C11	120.9 (3)
O2—C3—H3B	109.2	C9^ii—C11—C10	119.7 (3)
O2—C3'—C4'	109 (1)	C9—C10—H10	119.5
O2—C3'—H3'1	109.9	C9^ii—C11—H11	120.2
O2—C3'—H3'2	109.9	C10—C9—O6	116.4 (3)
Co1—O1—H1	126.7	C10—C9—C11^ii	119.4 (4)
Co1—O2—H2	123.4	C10—C11—H11	120.2
N1^i—Co1—N1	180	C11^ii—C9—O6	124.2 (3)
N1—C2—C1	105.5 (7)	C11—C10—H10	119.5
N1—C2—H2A	110.6	C1'—O1—Co1	115.7 (4)
N1—C2—H2B	110.6	C1'—O1—H1	116.4
N1—C4—H4A	109.7	C1'—C2'—N1	114.4 (8)
N1—C4—H4B	109.7	C1'—C2'—H2'1	108.7
N1—C6—C5	119.6 (4)	C1'—C2'—H2'2	108.7
N1—C6—H6A	107.4	C2'—N1—Co1	100.2 (3)
N1—C6—H6B	107.4	C2'—N1—C4	145.9 (5)
N1—C2'—H2'1	108.7	C2'—C1'—H1'1	110.2
N1—C2'—H2'2	108.7	C2'—C1'—H1'2	110.2
N1—C4'—C3'	111.3 (9)	C3'—O2—Co1	108.8 (6)
N1—C4'—H4'1	109.4	C3'—O2—H2	126.6
N1—C4'—H4'2	109.4	C3'—C4'—H4'1	109.4
O3—C5—C6	110.7 (4)	C3'—C4'—H4'2	109.4
O3—C5—H5A	109.5	C4'—N1—Co1	108.2 (4)
O3—C5—H5B	109.5	C4'—N1—C2	75.9 (5)
O4—C7—C8	114.4 (3)	C4'—N1—C2'	112.4 (5)
O5—C7—O4	126.9 (3)	C4'—C3'—H3'1	109.9
O5—C7—C8	118.6 (3)	C4'—C3'—H3'2	109.9
O6—C8—C7	115.9 (3)	H1A—C1—H1B	107.8
O6—C8—H8A	108.3	H2A—C2—H2B	108.8
O6—C8—H8B	108.3	H3A—C3—H3B	107.9
C1—O1—Co1	106.6 (5)	H4A—C4—H4B	108.2
C1—O1—H1	126.7	H5A—C5—H5B	108.1
C1—C2—H2A	110.6	H6A—C6—H6B	107.0
C1—C2—H2B	110.6	H8A—C8—H8B	107.4
C2—N1—Co1	107.6 (3)	H1'1—C1'—H1'2	108.5
C2—N1—C4	110.8 (5)	H2'1—C2'—H2'2	107.6
C2—C1—H1A	109.1	H3'1—C3'—H3'2	108.3
C2—C1—H1B	109.1	H4'1—C4'—H4'2	108.0
Co1—N1—C2—C1	36.0 (8)	O2—Co1—N1—C4'	3.0 (4)
Co1—N1—C4—C3	50 (1)	O2^i—Co1—N1—C4'	−177.0 (4)
Co1—N1—C6—C5	176.5 (4)	O2—Co1—O1—C1	−98.9 (9)
Co1—N1—C2'—C1'	−47.5 (9)	O2^i—Co1—O1—C1	81.1 (9)
Co1—N1—C4'—C3'	−29 (1)	O2—Co1—O1—C1'	−86 (1)
Co1—O1—C1—C2	47 (1)	O2^i—Co1—O1—C1'	94 (1)
Co1—O1—C1'—C2'	−19 (2)	O2—C3—C4—N1	−43 (2)
Co1—O2—C3—C4	13 (2)	O2—C3'—C4'—N1	51 (2)
Co1—O2—C3'—C4'	−47 (2)	O3—C5—C6—N1	159.9 (5)
N1—Co1—O1—C1	−18.5 (9)	O4—C7—C8—O6	167.8 (3)
N1^i—Co1—O1—C1	161.5 (9)	O5—C7—C8—O6	−14.2 (5)
N1—Co1—O1—C1'	−6 (1)	O6—C9—C10—C11	−179.4 (3)
N1^i—Co1—O1—C1'	175 (1)	C1—O1—C1'—C2'	37 (3)
N1^i—Co1—O2—C3	−167 (1)	C2—N1—C4—C3	−65 (1)
N1—Co1—O2—C3	13 (1)	C2—N1—C6—C5	−54.5 (8)
N1—Co1—O2—C3'	24 (1)	C2—N1—C2'—C1'	58 (1)
N1^i—Co1—O2—C3'	−156 (1)	C2—N1—C4'—C3'	−133 (1)
O1^i—Co1—N1—C2	169.4 (4)	C3—O2—C3'—C4'	68 (4)
O1—Co1—N1—C2	−10.6 (4)	C4—N1—C2—C1	146.8 (8)
O1^i—Co1—N1—C4	52.7 (3)	C4—N1—C6—C5	68.2 (7)
O1—Co1—N1—C4	−127.3 (3)	C4—N1—C2'—C1'	83 (1)
O1^i—Co1—N1—C6	−55.1 (4)	C4—N1—C4'—C3'	56 (1)
O1—Co1—N1—C6	124.9 (4)	C6—N1—C2—C1	−95.2 (9)
O1^i—Co1—N1—C2'	−153.3 (3)	C6—N1—C4—C3	166 (1)
O1—Co1—N1—C2'	26.7 (3)	C6—N1—C2'—C1'	−161.3 (9)
O1^i—Co1—N1—C4'	88.9 (4)	C6—N1—C4'—C3'	109 (1)
O1—Co1—N1—C4'	−91.1 (4)	C8—O6—C9—C10	−160.9 (3)
O1^i—Co1—O2—C3	−86 (1)	C8—O6—C9—C11^ii	20.1 (5)
O1—Co1—O2—C3	94 (1)	C9—O6—C8—C7	−81.2 (4)
O1—Co1—O2—C3'	106 (1)	C9—C10—C11—C9^ii	0.3 (6)
O1^i—Co1—O2—C3'	−74 (1)	C11^ii—C9—C10—C11	−0.3 (6)
O1—C1—C2—N1	−57 (1)	C1'—O1—C1—C2	−82 (4)
O1—C1'—C2'—N1	46 (2)	C2'—N1—C2—C1	−47.5 (9)
O2—Co1—N1—C2	83.6 (4)	C2'—N1—C4—C3	−80 (2)
O2^i—Co1—N1—C2	−96.4 (4)	C2'—N1—C6—C5	−80.9 (7)
O2—Co1—N1—C4	−33.1 (3)	C2'—N1—C4'—C3'	−139 (1)
O2^i—Co1—N1—C4	146.9 (3)	C3'—O2—C3—C4	−57 (4)
O2—Co1—N1—C6	−140.9 (4)	C4'—N1—C2—C1	141.0 (9)
O2^i—Co1—N1—C6	39.1 (4)	C4'—N1—C4—C3	−55 (1)
O2—Co1—N1—C2'	120.9 (3)	C4'—N1—C2'—C1'	67 (1)
O2^i—Co1—N1—C2'	−59.1 (3)	C4'—N1—C6—C5	40.3 (9)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4^iii	0.93	1.93	2.564 (4)	123
O2—H2···O5^iii	0.93	2.17	2.597 (3)	107
O3—H3···O4	0.82	2.01	2.743 (5)	148

Symmetry code: (iii) x+1/2, −y+1/2, z−1/2.