Diaqua­bis(ethyl­enediamine-κ²N,N′)copper(II) bis­(4-aminona­phthalene-1-sulfonate) dihydrate

In the title compound, [Cu(C₂H₈N₂)₂(H₂O)₂](C₁₀H₈NO₃S)₂·2H₂O, the Cu^II complex cation, located on an inversion centre, has a distorted octa­hedral coordination geometry formed by two ethyl­enediamine and two water mol­ecules. The distance of 3.4987 (11) Å between the centroids of neighbouring parallel aromatic rings of aminona­phthalenesulfonate anions suggests the existence of π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.037
• wR factor = 0.120
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

[Diaquabis(ethylenediamine)copper(II)] [bis(4-aminonaphthalene-1-sulfonate)] dihydrate

Crystal data

[Cu(C2H8N2)2(H2O)2](C10H8NO3S)2·2H2O	F(000) = 734
Mr = 700.28	Dx = 1.567 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4417 reflections
a = 12.4376 (9) Å	θ = 2.3–28.1°
b = 9.5950 (7) Å	µ = 0.94 mm^−1
c = 12.4375 (9) Å	T = 292 K
β = 90.03 (1)°	Block, blue
V = 1484.28 (19) Å^3	0.26 × 0.26 × 0.18 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 27.5°, θmin = 1.6°
φ and ω scans	h = −9→16
9813 measured reflections	k = −12→11
3382 independent reflections	l = −16→16

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0743P)^2] where P = (Fo^2 + 2Fc^2)/3
3382 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.39 e Å^−3
10 restraints	Δρmin = −0.48 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	0.02789 (14)
N1	−0.00237 (17)	0.1576 (2)	0.60916 (16)	0.0369 (4)
N2	0.01493 (17)	0.1545 (2)	0.39165 (16)	0.0351 (4)
C1	−0.0311 (2)	0.2857 (3)	0.5518 (2)	0.0439 (6)
H1C	−0.0134	0.3666	0.5951	0.053*
H1D	−0.1076	0.2873	0.5368	0.053*
C2	0.0327 (2)	0.2876 (3)	0.4473 (2)	0.0462 (6)
H2C	0.0090	0.3643	0.4023	0.055*
H2D	0.1086	0.2998	0.4624	0.055*
C3	0.38021 (16)	0.0538 (2)	0.18314 (16)	0.0256 (4)
C4	0.43634 (18)	−0.0453 (2)	0.24095 (16)	0.0306 (4)
H4	0.4009	−0.0994	0.2919	0.037*
C5	0.54668 (18)	−0.0646 (2)	0.22307 (17)	0.0322 (5)
H5	0.5835	−0.1312	0.2630	0.039*
C6	0.60123 (18)	0.0121 (2)	0.14849 (17)	0.0269 (4)
C7	0.54691 (15)	0.1191 (2)	0.09020 (14)	0.0232 (4)
C8	0.60105 (16)	0.2044 (2)	0.01514 (16)	0.0308 (5)
H8	0.6743	0.1919	0.0039	0.037*
C9	0.54763 (18)	0.3048 (2)	−0.04102 (17)	0.0352 (5)
H9	0.5845	0.3602	−0.0900	0.042*
C10	0.43742 (18)	0.3246 (2)	−0.02511 (17)	0.0333 (5)
H10	0.4015	0.3931	−0.0640	0.040*
C11	0.38216 (16)	0.2452 (2)	0.04630 (15)	0.0280 (4)
H11	0.3089	0.2603	0.0557	0.034*
C12	0.43434 (15)	0.13924 (19)	0.10693 (14)	0.0223 (4)
N3	0.71228 (16)	−0.0097 (2)	0.13407 (18)	0.0338 (4)
O1	0.21271 (14)	−0.04208 (19)	0.28290 (14)	0.0433 (4)
O2	0.20875 (13)	0.20108 (19)	0.23210 (14)	0.0449 (4)
O3	0.19277 (14)	0.02160 (19)	0.09616 (14)	0.0439 (4)
O4	0.19541 (16)	−0.0063 (2)	0.5137 (2)	0.0483 (5)
O5	0.20231 (17)	0.6756 (3)	0.20565 (17)	0.0523 (5)
S1	0.23869 (4)	0.06051 (6)	0.19907 (4)	0.03067 (16)
H4A	0.225 (2)	−0.024 (3)	0.457 (2)	0.049 (9)*
H4B	0.224 (2)	−0.057 (3)	0.552 (2)	0.052 (10)*
H5A	0.214 (3)	0.618 (4)	0.259 (3)	0.093 (13)*
H5B	0.209 (4)	0.744 (5)	0.237 (4)	0.13 (2)*
H2A	0.068 (2)	0.137 (3)	0.351 (2)	0.040 (7)*
H3A	0.731 (2)	−0.004 (2)	0.074 (2)	0.029 (7)*
H3B	0.7294 (19)	−0.084 (3)	0.158 (2)	0.033 (7)*
H1A	−0.055 (2)	0.137 (3)	0.662 (2)	0.055 (8)*
H1B	0.063 (2)	0.170 (3)	0.634 (2)	0.052 (8)*
H2B	−0.050 (2)	0.156 (3)	0.357 (2)	0.072 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0282 (2)	0.0276 (2)	0.0278 (2)	0.00022 (13)	0.00489 (15)	−0.00159 (13)
N1	0.0321 (11)	0.0395 (11)	0.0390 (10)	−0.0018 (9)	0.0055 (9)	−0.0087 (8)
N2	0.0298 (10)	0.0375 (11)	0.0380 (10)	−0.0012 (8)	0.0068 (8)	0.0042 (8)
C1	0.0441 (14)	0.0309 (12)	0.0566 (15)	0.0013 (10)	0.0066 (12)	−0.0105 (11)
C2	0.0489 (15)	0.0355 (13)	0.0544 (15)	−0.0077 (11)	0.0092 (12)	0.0036 (11)
C3	0.0272 (10)	0.0242 (9)	0.0254 (9)	0.0022 (8)	0.0038 (8)	−0.0035 (8)
C4	0.0364 (12)	0.0305 (10)	0.0248 (9)	0.0001 (9)	0.0035 (9)	0.0046 (8)
C5	0.0355 (12)	0.0325 (11)	0.0285 (10)	0.0063 (9)	−0.0016 (9)	0.0047 (8)
C6	0.0270 (11)	0.0270 (10)	0.0268 (10)	0.0026 (8)	−0.0023 (8)	−0.0060 (7)
C7	0.0253 (10)	0.0234 (9)	0.0210 (8)	−0.0007 (8)	0.0018 (7)	−0.0042 (7)
C8	0.0276 (11)	0.0324 (11)	0.0324 (10)	−0.0038 (8)	0.0050 (8)	−0.0025 (8)
C9	0.0413 (12)	0.0319 (11)	0.0325 (11)	−0.0053 (10)	0.0101 (9)	0.0062 (9)
C10	0.0390 (12)	0.0286 (10)	0.0323 (10)	0.0038 (9)	0.0005 (9)	0.0037 (8)
C11	0.0268 (10)	0.0283 (10)	0.0289 (9)	0.0037 (8)	0.0010 (8)	−0.0011 (8)
C12	0.0249 (10)	0.0219 (9)	0.0201 (8)	0.0011 (7)	0.0016 (7)	−0.0046 (7)
N3	0.0270 (10)	0.0392 (12)	0.0351 (11)	0.0073 (8)	0.0005 (9)	−0.0020 (8)
O1	0.0405 (10)	0.0472 (10)	0.0421 (9)	−0.0034 (8)	0.0188 (8)	0.0091 (8)
O2	0.0383 (9)	0.0388 (10)	0.0575 (10)	0.0081 (7)	0.0182 (8)	−0.0048 (8)
O3	0.0291 (9)	0.0599 (11)	0.0428 (10)	−0.0032 (8)	−0.0019 (8)	−0.0044 (8)
O4	0.0325 (10)	0.0605 (14)	0.0519 (12)	0.0021 (8)	0.0048 (9)	−0.0011 (10)
O5	0.0519 (12)	0.0479 (12)	0.0571 (11)	−0.0024 (9)	−0.0177 (9)	0.0036 (10)
S1	0.0268 (3)	0.0343 (3)	0.0309 (3)	0.0005 (2)	0.0108 (2)	−0.0001 (2)

Geometric parameters (Å, º)

Cu1—N1	2.0323 (19)	C5—H5	0.9300
Cu1—N1^i	2.0323 (19)	C6—N3	1.409 (3)
Cu1—N2^i	2.0119 (19)	C6—C7	1.427 (3)
Cu1—N2	2.0119 (19)	C7—C8	1.413 (3)
Cu1—O4^i	2.437 (2)	C7—C12	1.429 (3)
Cu1—O4	2.437 (2)	C8—C9	1.362 (3)
N1—C1	1.466 (3)	C8—H8	0.9300
N1—H1A	0.95 (3)	C9—C10	1.398 (3)
N1—H1B	0.88 (2)	C9—H9	0.9300
N2—C2	1.469 (3)	C10—C11	1.357 (3)
N2—H2A	0.86 (2)	C10—H10	0.9300
N2—H2B	0.92 (3)	C11—C12	1.422 (3)
C1—C2	1.523 (4)	C11—H11	0.9300
C1—H1C	0.9700	N3—H3A	0.78 (2)
C1—H1D	0.9700	N3—H3B	0.80 (2)
C2—H2C	0.9700	O1—S1	1.4701 (17)
C2—H2D	0.9700	O2—S1	1.4583 (18)
C3—C4	1.381 (3)	O3—S1	1.4502 (18)
C3—C12	1.423 (3)	O4—H4A	0.81 (3)
C3—S1	1.773 (2)	O4—H4B	0.77 (3)
C4—C5	1.403 (3)	O5—H5A	0.87 (3)
C4—H4	0.9300	O5—H5B	0.77 (4)
C5—C6	1.365 (3)
N2^i—Cu1—N2	180.0	C12—C3—S1	121.57 (15)
N2^i—Cu1—N1	95.70 (9)	C3—C4—C5	120.2 (2)
N2—Cu1—N1	84.30 (9)	C3—C4—H4	119.9
N2^i—Cu1—N1^i	84.30 (9)	C5—C4—H4	119.9
N2—Cu1—N1^i	95.70 (9)	C6—C5—C4	121.55 (19)
N1—Cu1—N1^i	180.0	C6—C5—H5	119.2
N2^i—Cu1—O4^i	88.45 (8)	C4—C5—H5	119.2
N2—Cu1—O4^i	91.55 (8)	C5—C6—N3	119.61 (19)
N1—Cu1—O4^i	90.77 (8)	C5—C6—C7	119.86 (19)
N1^i—Cu1—O4^i	89.23 (8)	N3—C6—C7	120.4 (2)
N2^i—Cu1—O4	91.55 (8)	C8—C7—C6	121.80 (18)
N2—Cu1—O4	88.45 (8)	C8—C7—C12	119.04 (17)
N1—Cu1—O4	89.23 (8)	C6—C7—C12	119.15 (18)
N1^i—Cu1—O4	90.77 (8)	C9—C8—C7	121.06 (19)
O4^i—Cu1—O4	180.0	C9—C8—H8	119.5
C1—N1—Cu1	107.62 (14)	C7—C8—H8	119.5
C1—N1—H1A	110.1 (17)	C8—C9—C10	120.10 (19)
Cu1—N1—H1A	108.9 (17)	C8—C9—H9	119.9
C1—N1—H1B	106.6 (19)	C10—C9—H9	119.9
Cu1—N1—H1B	108.5 (18)	C11—C10—C9	120.86 (19)
H1A—N1—H1B	115 (2)	C11—C10—H10	119.6
C2—N2—Cu1	109.81 (15)	C9—C10—H10	119.6
C2—N2—H2A	109.8 (17)	C10—C11—C12	121.14 (19)
Cu1—N2—H2A	109.0 (17)	C10—C11—H11	119.4
C2—N2—H2B	110 (2)	C12—C11—H11	119.4
Cu1—N2—H2B	105 (2)	C11—C12—C3	123.32 (18)
H2A—N2—H2B	114 (3)	C11—C12—C7	117.79 (17)
N1—C1—C2	107.3 (2)	C3—C12—C7	118.89 (17)
N1—C1—H1C	110.2	C6—N3—H3A	113.8 (19)
C2—C1—H1C	110.2	C6—N3—H3B	110.3 (18)
N1—C1—H1D	110.2	H3A—N3—H3B	109 (2)
C2—C1—H1D	110.2	Cu1—O4—H4A	114 (2)
H1C—C1—H1D	108.5	Cu1—O4—H4B	122 (2)
N2—C2—C1	108.30 (19)	H4A—O4—H4B	101 (3)
N2—C2—H2C	110.0	H5A—O5—H5B	98 (4)
C1—C2—H2C	110.0	O3—S1—O2	112.72 (11)
N2—C2—H2D	110.0	O3—S1—O1	111.53 (11)
C1—C2—H2D	110.0	O2—S1—O1	111.30 (10)
H2C—C2—H2D	108.4	O3—S1—C3	106.42 (10)
C4—C3—C12	120.28 (19)	O2—S1—C3	108.59 (10)
C4—C3—S1	117.94 (17)	O1—S1—C3	105.87 (10)
N2^i—Cu1—N1—C1	−160.05 (15)	C12—C7—C8—C9	0.0 (3)
N2—Cu1—N1—C1	19.95 (15)	C7—C8—C9—C10	−0.1 (3)
O4^i—Cu1—N1—C1	−71.53 (16)	C8—C9—C10—C11	0.2 (3)
O4—Cu1—N1—C1	108.47 (16)	C9—C10—C11—C12	−0.2 (3)
N1—Cu1—N2—C2	8.66 (16)	C10—C11—C12—C3	179.64 (19)
N1^i—Cu1—N2—C2	−171.34 (16)	C10—C11—C12—C7	0.0 (3)
O4^i—Cu1—N2—C2	99.28 (16)	C4—C3—C12—C11	−178.63 (19)
O4—Cu1—N2—C2	−80.72 (16)	S1—C3—C12—C11	6.6 (3)
Cu1—N1—C1—C2	−43.5 (2)	C4—C3—C12—C7	1.0 (3)
Cu1—N2—C2—C1	−34.7 (3)	S1—C3—C12—C7	−173.75 (14)
N1—C1—C2—N2	52.1 (3)	C8—C7—C12—C11	0.1 (3)
C12—C3—C4—C5	−1.5 (3)	C6—C7—C12—C11	−178.98 (17)
S1—C3—C4—C5	173.44 (16)	C8—C7—C12—C3	−179.56 (18)
C3—C4—C5—C6	−0.5 (3)	C6—C7—C12—C3	1.4 (3)
C4—C5—C6—N3	179.31 (19)	C4—C3—S1—O3	−114.28 (18)
C4—C5—C6—C7	2.9 (3)	C12—C3—S1—O3	60.59 (18)
C5—C6—C7—C8	177.65 (19)	C4—C3—S1—O2	124.12 (18)
N3—C6—C7—C8	1.3 (3)	C12—C3—S1—O2	−61.01 (18)
C5—C6—C7—C12	−3.3 (3)	C4—C3—S1—O1	4.5 (2)
N3—C6—C7—C12	−179.69 (17)	C12—C3—S1—O1	179.38 (16)
C6—C7—C8—C9	179.02 (19)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1	0.81 (3)	2.18 (3)	2.899 (3)	148 (3)
O4—H4B···O5^ii	0.77 (3)	2.24 (3)	2.888 (3)	142 (3)
O5—H5A···N3^iii	0.87 (3)	2.03 (3)	2.875 (3)	162 (4)
O5—H5B···O1^iv	0.77 (4)	2.13 (4)	2.877 (3)	165 (5)
N1—H1A···O1^i	0.95 (3)	2.27 (3)	3.143 (3)	152 (2)
N1—H1B···O2^ii	0.88 (2)	2.51 (3)	3.327 (3)	155 (2)
N2—H2A···O2	0.86 (2)	2.37 (3)	3.155 (3)	153 (2)
N2—H2B···O5^v	0.92 (3)	2.06 (3)	2.967 (3)	173 (3)
N3—H3A···O3^vi	0.78 (2)	2.33 (3)	3.100 (3)	170 (2)
N3—H3B···O2^vii	0.80 (2)	2.59 (3)	3.381 (3)	169 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x, y+1, z; (v) −x, y−1/2, −z+1/2; (vi) −x+1, −y, −z; (vii) −x+1, y−1/2, −z+1/2.