Literature DB >> 21578685

Bis(4-amino-benzene-sulfonato-κO)bis-(propane-1,3-diamine-κN,N')copper(II) dihydrate.

Ke-Juan Zhang, Xiang-Gao Meng, Xiu-Ling Li.

Abstract

In the title compound, [Cu(C(3)H(10)N(2))(2)(C(6)H(6)NO(3)S)(2)]·2H(2)O, the Cu(II) atom lies on an inversion center and is hexa-coordinated by four N atoms from two 1,3-diamino-propane ligands and two O atoms from two 4-amino-benzene-sulfonate ligands in a trans arrangement, displaying a distorted and axially elongated octa-hedral coordination geometry, with the O atoms at the axial positions. A three-dimensional network is formed in the crystal structure through O-H⋯O, N-H⋯O and N-H⋯N hydrogen bonds.

Entities: CellLine Chemical Disease Species

Year: 2009 PMID： 21578685 PMCID： PMC2972104 DOI： 10.1107/S1600536809049769

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to crystal engineering based on metal and organic building blocks, see: Evans & Lin (2002 ▶); Li et al. (2003 ▶, 2004 ▶). For related structures, see: Kim & Lee (2002 ▶); Sundberg et al. (2001 ▶); Sundberg & Sillanpää (1993 ▶); Sundberg & Uggla (1997 ▶); Wang et al. (2002 ▶). For the synthesis, see: Gunderman et al. (1996 ▶).

Experimental

Crystal data

[Cu(C3H10N2)2(C6H6NO3S)2]·2H2O M = 592.19 Monoclinic, a = 9.5171 (1) Å b = 10.3875 (4) Å c = 13.1646 (5) Å β = 101.256 (2)° V = 1276.40 (7) Å3 Z = 2 Mo Kα radiation μ = 1.07 mm−1 T = 293 K 0.48 × 0.20 × 0.18 mm

Data collection

Siemens SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.627, T max = 0.830 3629 measured reflections 2230 independent reflections 1889 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.132 S = 1.09 2230 reflections 161 parameters 3 restraints H-atom parameters constrained Δρmax = 0.48 e Å−3 Δρmin = −0.41 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049769/hy2252sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049769/hy2252Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C₃H₁₀N₂)₂(C₆H₆NO₃S)₂]·2H₂O	F(000) = 622
M_r = 592.19	D_x = 1.541 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2312 reflections
a = 9.5171 (1) Å	θ = 2.2–25.1°
b = 10.3875 (4) Å	µ = 1.07 mm⁻¹
c = 13.1646 (5) Å	T = 293 K
β = 101.256 (2)°	Prism, blue
V = 1276.40 (7) Å³	0.48 × 0.20 × 0.18 mm
Z = 2

Siemens SMART 1000 CCD diffractometer	2230 independent reflections
Radiation source: fine-focus sealed tube	1889 reflections with I > 2σ(I)
graphite	R_int = 0.024
φ and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.627, T_max = 0.830	k = −7→12
3629 measured reflections	l = −15→10

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0669P)² + 1.3129P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2230 reflections	Δρ_max = 0.48 e Å⁻³
161 parameters	Δρ_min = −0.41 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.054 (4)

	x	y	z	U_iso*/U_eq
Cu	0.5000	0.0000	0.5000	0.0387 (3)
N1	0.3723 (3)	−0.1305 (3)	0.5539 (2)	0.0470 (7)
H1A	0.3788	−0.2043	0.5193	0.056*
H1B	0.4125	−0.1457	0.6205	0.056*
N2	0.3801 (3)	0.1490 (3)	0.5351 (2)	0.0457 (7)
H2A	0.4171	0.1731	0.6005	0.055*
H2B	0.3929	0.2153	0.4938	0.055*
C1	0.2183 (4)	−0.1079 (4)	0.5506 (3)	0.0565 (10)
H1C	0.1820	−0.1742	0.5905	0.068*
H1D	0.1669	−0.1143	0.4796	0.068*
C2	0.1902 (4)	0.0226 (4)	0.5934 (3)	0.0537 (10)
H2C	0.0902	0.0277	0.5990	0.064*
H2D	0.2476	0.0314	0.6625	0.064*
C3	0.2240 (4)	0.1327 (4)	0.5273 (3)	0.0519 (9)
H3A	0.1794	0.1169	0.4557	0.062*
H3B	0.1840	0.2116	0.5491	0.062*
O1W	0.5872 (4)	−0.1325 (5)	0.1104 (5)	0.147 (2)
H1WA	0.5115	−0.0876	0.0934	0.221*
H1WB	0.5700	−0.1840	0.1563	0.221*
S	0.31964 (10)	0.04586 (13)	0.21957 (7)	0.0585 (4)
O1	0.3474 (3)	−0.0243 (3)	0.3153 (3)	0.0735 (10)
O2	0.3401 (4)	−0.0303 (6)	0.1333 (3)	0.156 (3)
O3	0.4010 (3)	0.1646 (4)	0.2294 (3)	0.0936 (13)
C11	0.1360 (4)	0.0876 (4)	0.1932 (2)	0.0435 (8)
C12	0.0384 (4)	0.0061 (4)	0.1338 (3)	0.0488 (9)
H12A	0.0702	−0.0675	0.1050	0.059*
C13	−0.1068 (4)	0.0337 (4)	0.1168 (3)	0.0527 (10)
H13A	−0.1717	−0.0220	0.0770	0.063*
C14	−0.1565 (4)	0.1431 (4)	0.1584 (3)	0.0483 (9)
C15	−0.0568 (4)	0.2261 (4)	0.2159 (3)	0.0523 (9)
H15A	−0.0880	0.3016	0.2424	0.063*
C16	0.0875 (4)	0.1982 (4)	0.2342 (3)	0.0493 (9)
H16A	0.1525	0.2538	0.2741	0.059*
N3	−0.3017 (3)	0.1723 (4)	0.1411 (3)	0.0680 (10)
H3D	−0.3627	0.1219	0.1039	0.082*
H3C	−0.3305	0.2407	0.1676	0.082*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0294 (4)	0.0433 (4)	0.0434 (4)	0.0037 (2)	0.0068 (2)	0.0027 (2)
N1	0.0377 (16)	0.0488 (17)	0.0541 (18)	0.0005 (13)	0.0079 (13)	0.0047 (14)
N2	0.0406 (16)	0.0493 (17)	0.0478 (17)	0.0061 (13)	0.0103 (13)	−0.0016 (14)
C1	0.0385 (19)	0.064 (2)	0.069 (3)	−0.0065 (18)	0.0147 (18)	−0.005 (2)
C2	0.039 (2)	0.076 (3)	0.049 (2)	0.0008 (18)	0.0162 (17)	−0.0048 (19)
C3	0.0358 (19)	0.068 (3)	0.051 (2)	0.0141 (17)	0.0058 (16)	−0.0058 (19)
O1W	0.061 (2)	0.130 (4)	0.254 (6)	−0.018 (2)	0.038 (3)	−0.109 (4)
S	0.0392 (5)	0.0932 (8)	0.0388 (5)	0.0172 (5)	−0.0031 (4)	0.0027 (5)
O1	0.0558 (18)	0.081 (2)	0.070 (2)	0.0005 (15)	−0.0221 (15)	0.0234 (16)
O2	0.067 (3)	0.294 (7)	0.091 (3)	0.084 (3)	−0.025 (2)	−0.090 (4)
O3	0.0430 (16)	0.125 (3)	0.109 (3)	−0.0080 (18)	0.0046 (17)	0.051 (2)
C11	0.0385 (18)	0.057 (2)	0.0331 (17)	0.0085 (16)	0.0022 (13)	0.0113 (15)
C12	0.049 (2)	0.051 (2)	0.042 (2)	0.0118 (16)	0.0005 (16)	0.0030 (16)
C13	0.044 (2)	0.053 (2)	0.056 (2)	−0.0013 (17)	−0.0026 (17)	0.0072 (18)
C14	0.0387 (19)	0.058 (2)	0.048 (2)	0.0050 (17)	0.0075 (15)	0.0182 (17)
C15	0.054 (2)	0.052 (2)	0.052 (2)	0.0129 (18)	0.0123 (17)	0.0032 (18)
C16	0.050 (2)	0.055 (2)	0.0408 (19)	0.0000 (17)	0.0035 (15)	0.0011 (16)
N3	0.0404 (18)	0.075 (2)	0.087 (3)	0.0107 (17)	0.0085 (17)	0.012 (2)

Cu—N1	2.038 (3)	O1W—H1WB	0.85
Cu—N2	2.029 (3)	S—O2	1.428 (4)
Cu—O1	2.589 (3)	S—O1	1.435 (3)
N1—C1	1.476 (4)	S—O3	1.448 (4)
N1—H1A	0.9000	S—C11	1.768 (3)
N1—H1B	0.9000	C11—C12	1.381 (5)
N2—C3	1.479 (4)	C11—C16	1.386 (5)
N2—H2A	0.9000	C12—C13	1.386 (6)
N2—H2B	0.9000	C12—H12A	0.9300
C1—C2	1.512 (5)	C13—C14	1.384 (6)
C1—H1C	0.9700	C13—H13A	0.9300
C1—H1D	0.9700	C14—N3	1.389 (5)
C2—C3	1.509 (6)	C14—C15	1.391 (6)
C2—H2C	0.9700	C15—C16	1.378 (5)
C2—H2D	0.9700	C15—H15A	0.9300
C3—H3A	0.9700	C16—H16A	0.9300
C3—H3B	0.9700	N3—H3D	0.8600
O1W—H1WA	0.85	N3—H3C	0.8600

N2—Cu—N2ⁱ	180.0	C1—C2—H2D	109.0
N2—Cu—N1	91.61 (13)	H2C—C2—H2D	107.8
N2ⁱ—Cu—N1	88.40 (13)	N2—C3—C2	111.8 (3)
N2—Cu—N1ⁱ	88.40 (13)	N2—C3—H3A	109.3
N2ⁱ—Cu—N1ⁱ	91.60 (13)	C2—C3—H3A	109.3
N1—Cu—N1ⁱ	180.0	N2—C3—H3B	109.3
N2—Cu—O1ⁱ	87.08 (11)	C2—C3—H3B	109.3
N2ⁱ—Cu—O1ⁱ	92.92 (11)	H3A—C3—H3B	107.9
N1—Cu—O1ⁱ	90.08 (11)	H1WA—O1W—H1WB	105.1
N1ⁱ—Cu—O1ⁱ	89.92 (11)	O2—S—O1	112.8 (3)
N2—Cu—O1	92.92 (11)	O2—S—O3	112.9 (3)
N2ⁱ—Cu—O1	87.08 (12)	O1—S—O3	110.5 (2)
N1—Cu—O1	89.92 (11)	O2—S—C11	105.22 (19)
N1ⁱ—Cu—O1	90.08 (11)	O1—S—C11	107.59 (18)
O1ⁱ—Cu—O1	180.0	O3—S—C11	107.44 (19)
C1—N1—Cu	122.7 (2)	S—O1—Cu	138.47 (19)
C1—N1—H1A	106.7	C12—C11—C16	119.4 (3)
Cu—N1—H1A	106.7	C12—C11—S	119.4 (3)
C1—N1—H1B	106.7	C16—C11—S	121.2 (3)
Cu—N1—H1B	106.7	C11—C12—C13	120.2 (4)
H1A—N1—H1B	106.6	C11—C12—H12A	119.9
C3—N2—Cu	119.9 (2)	C13—C12—H12A	119.9
C3—N2—H2A	107.3	C14—C13—C12	120.8 (4)
Cu—N2—H2A	107.3	C14—C13—H13A	119.6
C3—N2—H2B	107.3	C12—C13—H13A	119.6
Cu—N2—H2B	107.3	C13—C14—N3	121.3 (4)
H2A—N2—H2B	106.9	C13—C14—C15	118.3 (3)
N1—C1—C2	112.3 (3)	N3—C14—C15	120.3 (4)
N1—C1—H1C	109.1	C16—C15—C14	121.0 (4)
C2—C1—H1C	109.1	C16—C15—H15A	119.5
N1—C1—H1D	109.1	C14—C15—H15A	119.5
C2—C1—H1D	109.1	C15—C16—C11	120.1 (4)
H1C—C1—H1D	107.9	C15—C16—H16A	119.9
C3—C2—C1	113.1 (3)	C11—C16—H16A	119.9
C3—C2—H2C	109.0	C14—N3—H3D	120.0
C1—C2—H2C	109.0	C14—N3—H3C	120.0
C3—C2—H2D	109.0	H3D—N3—H3C	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2	0.85	1.90	2.651 (5)	146
O1W—H1WB···O3ⁱⁱ	0.85	2.16	2.969 (8)	160
N1—H1A···N3ⁱⁱⁱ	0.90	2.46	3.250 (5)	147
N1—H1B···O3ⁱ	0.90	2.39	3.243 (4)	158
N2—H2A···O3^iv	0.90	2.42	3.183 (4)	143
N2—H2B···O1W^v	0.90	2.13	3.025 (5)	177
N3—H3D···O1W^vi	0.86	2.69	3.337 (6)	133
N3—H3C···O1^vii	0.86	2.46	3.248 (5)	153

Table 1

Selected bond lengths (Å)

Cu—N1	2.038 (3)
Cu—N2	2.029 (3)
Cu—O1	2.589 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2	0.85	1.90	2.651 (5)	146
O1W—H1WB⋯O3ⁱ	0.85	2.16	2.969 (8)	160
N1—H1A⋯N3ⁱⁱ	0.90	2.46	3.250 (5)	147
N1—H1B⋯O3ⁱⁱⁱ	0.90	2.39	3.243 (4)	158
N2—H2A⋯O3^iv	0.90	2.42	3.183 (4)	143
N2—H2B⋯O1W ^v	0.90	2.13	3.025 (5)	177
N3—H3D⋯O1W ^vi	0.86	2.69	3.337 (6)	133
N3—H3C⋯O1^vii	0.86	2.46	3.248 (5)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

4 in total

1. Crystal engineering of NLO materials based on metal--organic coordination networks.

Authors: Owen R Evans; Wenbin Lin
Journal: Acc Chem Res Date: 2002-07 Impact factor: 22.384

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

3. Novel hydrogen-bonded three-dimensional networks encapsulating one-dimensional covalent chains: [M(4,4'-bipy)(H2O)(4)](4-abs)(2).nH2O (4,4'-bipy = 4,4'-bipyridine; 4-abs = 4-aminobenzenesulfonate) (M = Co, n = 1; M = Mn, n = 2).

Authors: Yonghui Wang; Liyun Feng; Yangguang Li; Changwen Hu; Enbo Wang; Ninghai Hu; Hengqing Jia
Journal: Inorg Chem Date: 2002-12-02 Impact factor: 5.165

4. Diaquabis(1,3-propanediamine-kappa(2)N,N')nickel(II) bis(sulfanilate).

Authors: Chong-Hyeak Kim; Sueg-Geun Lee
Journal: Acta Crystallogr C Date: 2002-06-29 Impact factor: 1.172

4 in total

1 in total

1. Diazido-bis(propane-1,3-diamine)copper(II).

Authors: Islam Ullah Khan; Onur Sahin; Orhan Büyükgüngör
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-03-24

1 in total