Bis(ethyl­enediamine-κ²N,N′)copper(II) 9,10-dioxoanthracene-2,6-disulfonate

In the title compound, [Cu(C₂H₈N₂)₂](C₁₄H₆O₈S₂), the Cu^II atom lies on an inversion centre and is coordinated by two ethyl­enediamine ligands in a square-planar geometry. 9,10-Dioxoanthracene-2,6-disulfonate anions, also lying on inversion centres, coordinate weakly to Cu^II and accept N—H...O hydrogen bonds from ethyl­enediamine, linking the [Cu(C₂H₈N₂)₂]²⁺ cations into chains. Adjacent chains are linked into extended two-dimensional networks via N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.087
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.13
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         300 Deg.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C4     -C7_b          1.45 Ang.

Alert level G
PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............          1 Times

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

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Bis(ethylenediamine-κ²N,N')copper(II) 9,10-dioxoanthracene-2,6-disulfonate

Crystal data

[Cu(C2H8N2)2](C14H6O8S2)	Z = 1
Mr = 550.06	F(000) = 283
Triclinic, P1	Dx = 1.773 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9738 (11) Å	Cell parameters from 4412 reflections
b = 8.3196 (14) Å	θ = 12–18°
c = 11.0372 (19) Å	µ = 1.32 mm^−1
α = 79.231 (3)°	T = 273 K
β = 78.946 (3)°	Block, blue
γ = 75.258 (3)°	0.32 × 0.26 × 0.20 mm
V = 515.11 (16) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2228 independent reflections
Radiation source: fine-focus sealed tube	1760 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.67, Tmax = 0.77	k = −10→10
4412 measured reflections	l = −14→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0406P)^2 + 0.2691P] where P = (Fo^2 + 2Fc^2)/3
2228 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.23 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
Cu1	0.0000	0.0000	0.5000	0.03089 (15)
S1	0.30573 (11)	0.19633 (8)	0.25059 (6)	0.02894 (16)
O1	0.1407 (3)	0.3498 (2)	0.2788 (2)	0.0463 (5)
O2	0.4030 (3)	0.0987 (3)	0.36019 (17)	0.0415 (5)
O3	0.2160 (4)	0.0968 (3)	0.18533 (19)	0.0469 (5)
O4	0.7449 (3)	0.6970 (2)	0.16757 (18)	0.0412 (5)
N1	0.0702 (4)	0.1022 (3)	0.6340 (2)	0.0340 (5)
H1A	0.0084	0.0559	0.7093	0.041*
H1B	0.2261	0.0834	0.6314	0.041*
N2	−0.2309 (4)	0.2193 (3)	0.4660 (2)	0.0339 (5)
H2A	−0.1750	0.2811	0.3961	0.041*
H2B	−0.3673	0.2008	0.4553	0.041*
C1	0.5428 (4)	0.2597 (3)	0.1453 (2)	0.0253 (5)
C2	0.6675 (4)	0.1612 (3)	0.0547 (2)	0.0308 (5)
H2	0.6242	0.0641	0.0474	0.037*
C3	0.8557 (4)	0.2087 (3)	−0.0241 (2)	0.0297 (5)
H3	0.9379	0.1439	−0.0855	0.036*
C4	0.9239 (4)	0.3528 (3)	−0.0127 (2)	0.0247 (5)
C5	0.7957 (4)	0.4525 (3)	0.0770 (2)	0.0238 (5)
C6	0.6032 (4)	0.4060 (3)	0.1557 (2)	0.0262 (5)
H6	0.5160	0.4728	0.2149	0.031*
C7	0.8628 (4)	0.6067 (3)	0.0930 (2)	0.0261 (5)
C8	−0.0320 (6)	0.2842 (4)	0.6140 (3)	0.0457 (7)
H8A	0.0694	0.3404	0.5500	0.055*
H8B	−0.0499	0.3307	0.6905	0.055*
C9	−0.2673 (5)	0.3092 (4)	0.5739 (3)	0.0448 (7)
H9A	−0.3747	0.2647	0.6416	0.054*
H9B	−0.3328	0.4279	0.5508	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0393 (3)	0.0274 (2)	0.0276 (3)	−0.00766 (19)	−0.00812 (19)	−0.00460 (18)
S1	0.0268 (3)	0.0330 (3)	0.0284 (3)	−0.0147 (3)	−0.0017 (2)	0.0006 (3)
O1	0.0340 (11)	0.0399 (11)	0.0571 (13)	−0.0091 (9)	0.0099 (9)	−0.0037 (10)
O2	0.0419 (11)	0.0503 (12)	0.0315 (10)	−0.0176 (9)	−0.0063 (8)	0.0068 (9)
O3	0.0473 (12)	0.0614 (13)	0.0432 (12)	−0.0356 (11)	−0.0035 (9)	−0.0064 (10)
O4	0.0389 (11)	0.0414 (11)	0.0460 (12)	−0.0165 (9)	0.0110 (9)	−0.0211 (9)
N1	0.0412 (13)	0.0335 (12)	0.0304 (12)	−0.0144 (10)	−0.0071 (10)	−0.0025 (9)
N2	0.0335 (12)	0.0355 (12)	0.0334 (12)	−0.0102 (9)	−0.0037 (9)	−0.0053 (9)
C1	0.0227 (12)	0.0304 (12)	0.0234 (12)	−0.0116 (9)	−0.0036 (9)	0.0021 (9)
C2	0.0339 (14)	0.0280 (13)	0.0354 (14)	−0.0153 (10)	−0.0046 (11)	−0.0063 (10)
C3	0.0324 (14)	0.0292 (13)	0.0294 (13)	−0.0110 (10)	0.0003 (10)	−0.0084 (10)
C4	0.0270 (12)	0.0244 (12)	0.0242 (12)	−0.0094 (9)	−0.0046 (9)	−0.0016 (9)
C5	0.0238 (12)	0.0250 (12)	0.0234 (12)	−0.0078 (9)	−0.0033 (9)	−0.0027 (9)
C6	0.0257 (12)	0.0314 (13)	0.0233 (12)	−0.0104 (10)	−0.0018 (9)	−0.0049 (10)
C7	0.0273 (12)	0.0273 (12)	0.0240 (12)	−0.0077 (10)	−0.0021 (10)	−0.0040 (10)
C8	0.067 (2)	0.0342 (15)	0.0428 (17)	−0.0172 (14)	−0.0134 (15)	−0.0106 (13)
C9	0.0486 (18)	0.0368 (16)	0.0461 (17)	−0.0004 (13)	−0.0053 (14)	−0.0130 (13)

Geometric parameters (Å, º)

Cu1—N1	1.994 (2)	C1—C2	1.392 (4)
Cu1—N1^i	1.994 (2)	C2—C3	1.378 (3)
Cu1—N2^i	2.009 (2)	C2—H2	0.930
Cu1—N2	2.009 (2)	C3—C4	1.395 (3)
S1—O3	1.445 (2)	C3—H3	0.930
S1—O1	1.445 (2)	C4—C5	1.396 (3)
S1—O2	1.4569 (19)	C4—C7^ii	1.482 (3)
S1—C1	1.776 (2)	C5—C6	1.394 (3)
O4—C7	1.216 (3)	C5—C7	1.487 (3)
N1—C8	1.473 (4)	C6—H6	0.930
N1—H1A	0.900	C7—C4^ii	1.482 (3)
N1—H1B	0.900	C8—C9	1.507 (4)
N2—C9	1.476 (3)	C8—H8A	0.970
N2—H2A	0.900	C8—H8B	0.970
N2—H2B	0.900	C9—H9A	0.970
C1—C6	1.384 (3)	C9—H9B	0.970
N1—Cu1—N1^i	180.0	C1—C2—H2	120.3
N1—Cu1—N2^i	94.83 (9)	C2—C3—C4	120.6 (2)
N1^i—Cu1—N2^i	85.17 (9)	C2—C3—H3	119.7
N1—Cu1—N2	85.17 (9)	C4—C3—H3	119.7
N1^i—Cu1—N2	94.83 (9)	C3—C4—C5	119.5 (2)
N2^i—Cu1—N2	180.0	C3—C4—C7^ii	119.1 (2)
O3—S1—O1	113.59 (13)	C5—C4—C7^ii	121.3 (2)
O3—S1—O2	112.45 (12)	C6—C5—C4	119.9 (2)
O1—S1—O2	112.11 (13)	C6—C5—C7	118.7 (2)
O3—S1—C1	105.75 (11)	C4—C5—C7	121.4 (2)
O1—S1—C1	105.80 (12)	C1—C6—C5	119.6 (2)
O2—S1—C1	106.42 (11)	C1—C6—H6	120.2
C8—N1—Cu1	108.41 (17)	C5—C6—H6	120.2
C8—N1—H1A	110.0	O4—C7—C4^ii	121.5 (2)
Cu1—N1—H1A	110.0	O4—C7—C5	121.1 (2)
C8—N1—H1B	110.0	C4^ii—C7—C5	117.3 (2)
Cu1—N1—H1B	110.0	N1—C8—C9	107.7 (2)
H1A—N1—H1B	108.4	N1—C8—H8A	110.2
C9—N2—Cu1	107.83 (17)	C9—C8—H8A	110.2
C9—N2—H2A	110.1	N1—C8—H8B	110.2
Cu1—N2—H2A	110.1	C9—C8—H8B	110.2
C9—N2—H2B	110.1	H8A—C8—H8B	108.5
Cu1—N2—H2B	110.1	N2—C9—C8	107.3 (2)
H2A—N2—H2B	108.5	N2—C9—H9A	110.2
C6—C1—C2	120.8 (2)	C8—C9—H9A	110.2
C6—C1—S1	119.33 (19)	N2—C9—H9B	110.2
C2—C1—S1	119.87 (18)	C8—C9—H9B	110.2
C3—C2—C1	119.5 (2)	H9A—C9—H9B	108.5
C3—C2—H2	120.3

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.90	2.12	2.922 (3)	149
N1—H1B···O2^iii	0.90	2.35	3.172 (3)	152
N2—H2A···O1	0.90	2.21	3.000 (3)	146
N2—H2B···O2^iv	0.90	2.28	3.113 (3)	154

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