metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Aqua­{2-[(3,5-di­chloro-2-oxido­benzyl­­idene)amino]-3-(4-hy­droxy­phen­yl)propionato-κ3O1,N,O2}copper(II) sesquihydrate

aKey Laboratory of Non-ferrous Metal Materials and Processing Technology, Department of Materials and Chemical Engineering, Guilin University of Technology, Ministry of Education, Guilin 541004, People's Republic of China
*Correspondence e-mail: lisa4.6@163.com

(Received 13 March 2008; accepted 28 April 2008; online 3 May 2008)

In the title compound, [Cu(C16H11Cl2NO4)(H2O)]·1.5H2O, the CuII atom is coordinated by two O atoms and one N atom from the 2-[(3,5-dichloro-2-oxidobenzyl­idene)amino]-3-(4-hydroxy­phen­yl)propionate ligand, and by the O atom from a water mol­ecule in a square-planar coordination. There are two formula units in the asymmetric unit. Molecules are further assembled into a three-dimensional network through C—H⋯Cl contacts, a Cu⋯Cl weak inter­action [3.161 (2) Å], O—H⋯O and C—H⋯O hydrogen bonds. The three water mol­ecules of the asymmetric unit are distributed over five positions with one full and two approximately half occupancies, while a tyrosine side chain in one of the complex mol­ecules is disordered over two positions [occupancies 0.507 (5) and 0.493 (5)].

Related literature

For related literature, see: Casella & Gullotti (1986[Casella, L. & Gullotti, M. (1986). Inorg. Chem. 25, 1293-1303.]); Guthrie et al. (1980[Guthrie, J. W., Lintvedt, R. L. & Glick, M. D. (1980). Inorg. Chem. 19, 2949-2955.]); Wang et al. (1994[Wang, Z., Wu, Z., Yen, Z., Le, Z., Zhu, X. & Huang, Q. (1994). Synth. React. Inorg. Met.-Org. Chem. 24, 1453-1460.]); Zhang et al. (2003[Zhang, S. H., Jiang, Y. M., Xiao, Y. & Zhou, Z. Y. (2003). Chin. J. Inorg. Chem. 19, 517-520.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C16H11Cl2NO4)(H2O)]·1.5H2O

  • Mr = 460.74

  • Triclinic, [P \overline 1]

  • a = 10.006 (2) Å

  • b = 13.899 (2) Å

  • c = 14.565 (2) Å

  • α = 70.469 (2)°

  • β = 87.427 (3)°

  • γ = 73.121 (3)°

  • V = 1823.8 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.53 mm−1

  • T = 293 (2) K

  • 0.40 × 0.18 × 0.09 mm

Data collection
  • Bruker SMART 1000 diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.580, Tmax = 0.875

  • 9183 measured reflections

  • 6315 independent reflections

  • 3605 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.143

  • S = 1.02

  • 6315 reflections

  • 583 parameters

  • H-atom parameters constrained

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O12i 0.82 1.88 2.643 (10) 154
O8—H8⋯O7ii 0.82 1.70 2.515 (9) 175
O5—H33⋯O6iii 0.85 1.89 2.714 (6) 164
O13—H42⋯Cl1iv 0.85 2.77 3.555 (9) 154
C26—H26⋯O3v 0.93 2.44 3.365 (7) 173
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) -x, -y+1, -z; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Schiff base complexes containing amino acids have been studied for many years(Casella & Gullotti, 1986; Wang et al., 1994; Zhang et al., 2003). Schiff bases have played an important role in the development of coordination chemistry as they form stable complexes with most of the transition metals.

In the asymmetric unit there are two CuII ions, two L ligand anions, two ligating water molecules and three water hydrate molecules (Fig. 1). The CuII cations are coordinated by two O atoms and one N atom from ligand L, then the O atom from an H2O coordinate to CuII. These four atoms form a square-planar coordination centered at the cuprate(II) ions (Fig. 1). The coordination in these two complexes in the asymmetric unit does not seem to be alike. There is a Cu···Cl distance of 3.161 (2) Å indicating a possible weak interaction between the two complexes in the asymmetric unit. Fig. 2 shows that the tyrosine in one of the complexes has two different orientations in this crystal giving a disordered structure. Weak contacts of C–H···Cl and Cu···Cl types and O–H···O hydrogen bonds construct a 3-D network running along the a axis (Fig.3).

Related literature top

For related literature, see: Casella & Gullotti (1986); Guthrie et al. (1980); Wang et al. (1994); Zhang et al. (2003).

Experimental top

An ethanol solution (5 ml) containing 3,5-dichloro-2-hydroxy-benzaldehyde (0.096 g, 0.5 mmol) was added to an aqueous solution containing 2-amino-3-(4-hydroxy-phenyl)-propionic acid (0.222 g, 2 mmol) and sodium hydroxide (0.091 g, 0.5 mmol). After stirring for 1 h, an aqueous solution of copper chloride (0.1 g, 0.5 mmol) was added to the resulting solution and stirred for 2 h. The green solution was filtered. After 10 days, green block crystals were obtained by slow evaporation of the filtrate (yield: 45.2%, based on Cu).

Refinement top

Water H atoms were located in a difference Fourier map and were allowed to ride on the O atom, with Uiso(H) = 1.5Ueq(O). All other H atoms were positioned geometrically and refined as riding, with C–H = 0.93 Å and with Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title complex showing 30% probability displacement ellipsoids. H atoms, except for the water molecules, are not shown.
[Figure 2] Fig. 2. The disordered tyrosine view in one of the complexes.
[Figure 3] Fig. 3. The three-dimensional network of Cu···Cl weak interactions and hydrogen bonds shown in dotted lines.
Aqua{2-[(3,5-dichloro-2-oxidobenzylidene)amino]-3-(4-hydroxyphenyl)propionato- κ3O1,N,O2}copper(II) sesquihydrate top
Crystal data top
[Cu(C16H11Cl2NO4)(H2O)]·1.5H2OZ = 4
Mr = 460.74F(000) = 936
Triclinic, P1Dx = 1.678 Mg m3
a = 10.006 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.899 (2) ÅCell parameters from 2332 reflections
c = 14.565 (2) Åθ = 2.3–25.2°
α = 70.469 (2)°µ = 1.53 mm1
β = 87.427 (3)°T = 293 K
γ = 73.121 (3)°Plate, green
V = 1823.8 (5) Å30.40 × 0.18 × 0.09 mm
Data collection top
Bruker SMART 1000
diffractometer
6315 independent reflections
Radiation source: fine-focus sealed tube3605 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.580, Tmax = 0.875k = 1216
9183 measured reflectionsl = 1617
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0669P)2]
where P = (Fo2 + 2Fc2)/3
6315 reflections(Δ/σ)max = 0.001
583 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Cu(C16H11Cl2NO4)(H2O)]·1.5H2Oγ = 73.121 (3)°
Mr = 460.74V = 1823.8 (5) Å3
Triclinic, P1Z = 4
a = 10.006 (2) ÅMo Kα radiation
b = 13.899 (2) ŵ = 1.53 mm1
c = 14.565 (2) ÅT = 293 K
α = 70.469 (2)°0.40 × 0.18 × 0.09 mm
β = 87.427 (3)°
Data collection top
Bruker SMART 1000
diffractometer
6315 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3605 reflections with I > 2σ(I)
Tmin = 0.580, Tmax = 0.875Rint = 0.027
9183 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.02Δρmax = 0.58 e Å3
6315 reflectionsΔρmin = 0.36 e Å3
583 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.46267 (7)0.15476 (5)0.36588 (4)0.0406 (2)
Cu20.01499 (6)0.64742 (5)0.11028 (4)0.0407 (2)
Cl10.87069 (17)0.11542 (12)0.34408 (11)0.0668 (5)
Cl21.07017 (15)0.16022 (11)0.69630 (11)0.0578 (4)
Cl30.39713 (16)0.37698 (11)0.12877 (10)0.0580 (4)
Cl40.58637 (15)0.33274 (11)0.22575 (11)0.0597 (4)
N10.5002 (4)0.1767 (3)0.4841 (3)0.0349 (10)
N20.0214 (5)0.6696 (4)0.0075 (3)0.0556 (13)
O10.2819 (4)0.2595 (3)0.3616 (2)0.0447 (9)
O20.1508 (4)0.3508 (3)0.4497 (3)0.0621 (12)
O30.8857 (4)0.3483 (4)0.7126 (3)0.0699 (12)
H30.95060.36220.67950.105*
O40.6311 (4)0.0441 (3)0.3785 (2)0.0454 (9)
O50.4122 (4)0.1358 (3)0.2489 (2)0.0552 (10)
H330.33330.16760.21740.083*
H340.46720.10720.21290.083*
O60.1909 (4)0.7570 (3)0.1170 (3)0.0508 (10)
O70.3148 (4)0.8569 (3)0.0328 (4)0.0801 (15)
O80.4986 (7)0.8913 (6)0.0835 (5)0.051 (2)0.507 (5)
H80.55640.88360.04290.077*0.507 (5)
O8'0.4246 (7)0.9296 (6)0.1086 (6)0.049 (2)0.493 (5)
H8'0.49120.90950.06910.074*0.493 (5)
O90.1554 (3)0.5378 (3)0.0977 (2)0.0459 (9)
O100.0682 (4)0.6254 (3)0.2247 (2)0.0547 (10)
H350.12830.67140.26900.082*
H360.03570.57310.24520.082*
O110.8440 (5)0.4610 (4)0.3037 (3)0.1056 (18)
H370.82720.51830.25480.158*
H380.82330.42170.27630.158*
O120.8592 (8)0.6491 (7)0.3412 (6)0.066 (3)0.522 (10)
H390.85290.66660.39220.098*0.522 (10)
H400.86430.58320.36370.098*0.522 (10)
O130.4751 (9)0.0597 (6)0.7508 (5)0.077 (3)0.523 (6)
H410.44220.09760.78650.116*0.523 (6)
H420.40760.05810.71840.116*0.523 (6)
O12'0.9281 (9)0.5554 (7)0.4185 (7)0.066 (4)0.478 (10)
H39'0.84730.55260.40640.098*0.478 (10)
H40'0.91550.59230.45610.098*0.478 (10)
O13'0.3267 (10)0.1743 (7)0.8023 (6)0.077 (3)0.477 (6)
H41'0.33860.16690.86200.116*0.477 (6)
H42'0.29320.12480.80190.116*0.477 (6)
C10.2626 (6)0.2932 (4)0.4349 (4)0.0468 (14)
C20.3934 (5)0.2649 (4)0.5020 (4)0.0404 (13)
H20.36980.24350.57050.048*
C30.4401 (5)0.3661 (4)0.4761 (4)0.0456 (14)
H3A0.46560.38460.40870.055*
H3B0.36130.42410.48090.055*
C40.5605 (5)0.3567 (4)0.5389 (4)0.0380 (13)
C50.5444 (6)0.3550 (4)0.6350 (4)0.0486 (15)
H5A0.45790.35640.66140.058*
C60.6528 (6)0.3515 (4)0.6913 (4)0.0474 (14)
H60.63880.35060.75510.057*
C70.7826 (6)0.3492 (4)0.6543 (4)0.0446 (14)
C80.8034 (6)0.3492 (4)0.5601 (4)0.0450 (14)
H8A0.89070.34710.53440.054*
C90.6932 (6)0.3523 (4)0.5041 (4)0.0429 (14)
H90.70830.35130.44090.051*
C100.6014 (5)0.1182 (4)0.5469 (4)0.0380 (13)
H10A0.60160.13230.60500.046*
C110.7153 (5)0.0322 (4)0.5356 (4)0.0383 (12)
C120.7253 (5)0.0025 (4)0.4506 (4)0.0395 (13)
C130.8490 (6)0.0788 (4)0.4477 (4)0.0452 (14)
C140.9516 (5)0.1270 (4)0.5211 (4)0.0433 (14)
H141.03060.17980.51580.052*
C150.9376 (5)0.0971 (4)0.6025 (4)0.0438 (14)
C160.8219 (5)0.0183 (4)0.6104 (4)0.0411 (13)
H160.81410.00170.66580.049*
C170.2082 (5)0.7943 (4)0.0462 (4)0.0420 (13)
C180.073 (2)0.7774 (14)0.0135 (14)0.038 (4)0.507 (5)
H180.09320.77050.08140.045*0.507 (5)
C190.0263 (11)0.8773 (8)0.0352 (8)0.045 (3)0.507 (5)
H19A0.02560.88940.10470.053*0.507 (5)
H19B0.09730.93730.02590.053*0.507 (5)
C200.1122 (19)0.8796 (15)0.0029 (15)0.042 (4)0.507 (5)
C210.140 (2)0.8750 (15)0.0908 (16)0.044 (4)0.507 (5)
H210.07450.86470.13740.053*0.507 (5)
C220.2662 (11)0.8858 (8)0.1162 (8)0.046 (3)0.507 (5)
H220.27840.89200.17670.055*0.507 (5)
C230.3739 (14)0.8875 (10)0.0528 (10)0.042 (3)0.507 (5)
C240.347 (6)0.887 (5)0.039 (5)0.044 (9)0.507 (5)
H240.41770.88870.08340.053*0.507 (5)
C250.218 (2)0.8852 (13)0.0675 (12)0.044 (4)0.507 (5)
H250.20230.88750.13070.053*0.507 (5)
C18'0.101 (2)0.7389 (15)0.0366 (14)0.036 (4)0.493 (5)
H18'0.14110.69480.09150.043*0.493 (5)
C19'0.0505 (10)0.8163 (8)0.0707 (8)0.038 (3)0.493 (5)
H19C0.12740.88110.05980.046*0.493 (5)
H19D0.02850.78450.14050.046*0.493 (5)
C20'0.0742 (19)0.8468 (15)0.0232 (13)0.032 (4)0.493 (5)
C21'0.0869 (12)0.8771 (8)0.0768 (9)0.040 (3)0.493 (5)
H21'0.01390.88110.11670.048*0.493 (5)
C22'0.2054 (19)0.9017 (13)0.1196 (11)0.042 (4)0.493 (5)
H22'0.21260.91910.18670.050*0.493 (5)
C23'0.313 (5)0.900 (5)0.062 (5)0.040 (8)0.493 (5)
C24'0.3069 (15)0.8696 (10)0.0395 (12)0.042 (3)0.493 (5)
H24'0.37850.86760.07920.051*0.493 (5)
C25'0.188 (2)0.8424 (17)0.0773 (17)0.046 (5)0.493 (5)
H25'0.18420.81920.14480.055*0.493 (5)
C260.1228 (6)0.6130 (5)0.0709 (4)0.0566 (16)
H260.12280.62900.12800.068*
C270.2371 (5)0.5265 (4)0.0609 (4)0.0420 (13)
C280.2481 (5)0.4970 (4)0.0244 (4)0.0371 (12)
C290.3733 (5)0.4155 (4)0.0259 (4)0.0386 (13)
C300.4740 (5)0.3672 (4)0.0480 (4)0.0422 (13)
H300.55420.31530.04310.051*
C310.4552 (6)0.3966 (4)0.1310 (4)0.0452 (14)
C320.3407 (5)0.4747 (4)0.1372 (4)0.0456 (14)
H320.33070.49430.19280.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0356 (4)0.0389 (4)0.0449 (4)0.0035 (3)0.0044 (3)0.0167 (3)
Cu20.0304 (4)0.0523 (4)0.0438 (4)0.0084 (3)0.0012 (3)0.0247 (3)
Cl10.0668 (11)0.0601 (10)0.0635 (10)0.0104 (8)0.0035 (8)0.0319 (8)
Cl20.0417 (9)0.0507 (9)0.0644 (10)0.0008 (7)0.0143 (7)0.0070 (7)
Cl30.0579 (10)0.0565 (9)0.0624 (9)0.0029 (8)0.0133 (8)0.0366 (8)
Cl40.0463 (9)0.0514 (9)0.0650 (10)0.0010 (7)0.0144 (7)0.0080 (7)
N10.032 (2)0.029 (2)0.042 (2)0.003 (2)0.000 (2)0.014 (2)
N20.034 (3)0.070 (3)0.063 (3)0.014 (2)0.008 (2)0.045 (3)
O10.034 (2)0.049 (2)0.051 (2)0.0024 (17)0.0083 (17)0.0244 (19)
O20.031 (2)0.069 (3)0.090 (3)0.005 (2)0.010 (2)0.046 (2)
O30.053 (3)0.105 (4)0.062 (3)0.022 (3)0.009 (2)0.039 (3)
O40.044 (2)0.041 (2)0.049 (2)0.0006 (17)0.0049 (19)0.0213 (18)
O50.045 (2)0.066 (3)0.053 (2)0.002 (2)0.0085 (18)0.031 (2)
O60.043 (2)0.052 (2)0.060 (2)0.0029 (19)0.0139 (19)0.030 (2)
O70.033 (2)0.079 (3)0.144 (4)0.008 (2)0.013 (3)0.075 (3)
O80.032 (4)0.060 (5)0.066 (5)0.006 (4)0.005 (4)0.033 (4)
O8'0.026 (4)0.054 (5)0.067 (6)0.013 (4)0.007 (4)0.021 (4)
O90.030 (2)0.062 (2)0.054 (2)0.0033 (18)0.0003 (18)0.039 (2)
O100.054 (3)0.062 (3)0.053 (2)0.007 (2)0.0147 (19)0.032 (2)
O110.103 (4)0.138 (5)0.078 (3)0.016 (4)0.013 (3)0.057 (3)
O120.060 (6)0.073 (7)0.078 (7)0.020 (5)0.012 (5)0.042 (6)
O130.090 (7)0.076 (6)0.069 (6)0.022 (5)0.004 (5)0.030 (5)
O12'0.060 (6)0.073 (8)0.078 (7)0.020 (5)0.012 (5)0.042 (6)
O13'0.090 (8)0.076 (7)0.069 (6)0.022 (6)0.004 (5)0.030 (5)
C10.041 (4)0.040 (3)0.060 (4)0.009 (3)0.005 (3)0.020 (3)
C20.030 (3)0.043 (3)0.045 (3)0.002 (3)0.007 (2)0.017 (3)
C30.043 (3)0.037 (3)0.052 (3)0.001 (3)0.008 (3)0.017 (3)
C40.038 (3)0.030 (3)0.043 (3)0.002 (2)0.005 (3)0.016 (2)
C50.037 (3)0.061 (4)0.052 (3)0.014 (3)0.010 (3)0.024 (3)
C60.047 (4)0.064 (4)0.034 (3)0.014 (3)0.001 (3)0.021 (3)
C70.040 (3)0.047 (3)0.047 (3)0.005 (3)0.008 (3)0.020 (3)
C80.032 (3)0.050 (3)0.057 (4)0.006 (3)0.004 (3)0.027 (3)
C90.048 (4)0.044 (3)0.040 (3)0.009 (3)0.006 (3)0.023 (3)
C100.045 (3)0.032 (3)0.036 (3)0.008 (3)0.003 (3)0.012 (2)
C110.035 (3)0.032 (3)0.044 (3)0.006 (2)0.002 (2)0.011 (2)
C120.040 (3)0.030 (3)0.045 (3)0.008 (3)0.000 (3)0.009 (2)
C130.049 (4)0.035 (3)0.050 (3)0.005 (3)0.006 (3)0.017 (3)
C140.036 (3)0.028 (3)0.054 (3)0.001 (2)0.002 (3)0.007 (3)
C150.028 (3)0.036 (3)0.055 (3)0.004 (3)0.006 (3)0.002 (3)
C160.042 (3)0.036 (3)0.046 (3)0.012 (3)0.001 (3)0.013 (3)
C170.027 (3)0.035 (3)0.061 (4)0.007 (3)0.000 (3)0.014 (3)
C180.027 (9)0.041 (12)0.047 (10)0.005 (7)0.002 (7)0.020 (8)
C190.032 (7)0.043 (7)0.061 (7)0.008 (5)0.008 (6)0.021 (6)
C200.031 (12)0.039 (11)0.054 (12)0.002 (7)0.002 (9)0.018 (8)
C210.032 (11)0.048 (12)0.053 (9)0.013 (9)0.005 (7)0.017 (8)
C220.041 (7)0.046 (7)0.053 (7)0.011 (5)0.003 (6)0.023 (6)
C230.034 (8)0.040 (7)0.054 (8)0.006 (6)0.002 (7)0.021 (6)
C240.04 (3)0.040 (16)0.06 (2)0.007 (17)0.006 (15)0.022 (15)
C250.036 (9)0.045 (9)0.052 (10)0.004 (7)0.009 (11)0.023 (9)
C18'0.024 (9)0.038 (12)0.047 (10)0.003 (7)0.012 (6)0.022 (8)
C19'0.032 (6)0.040 (7)0.045 (6)0.009 (5)0.000 (5)0.019 (5)
C20'0.024 (9)0.036 (11)0.042 (10)0.007 (6)0.004 (7)0.021 (8)
C21'0.030 (7)0.042 (7)0.048 (7)0.008 (5)0.003 (6)0.016 (6)
C22'0.034 (8)0.046 (9)0.049 (9)0.009 (6)0.004 (9)0.021 (9)
C23'0.03 (2)0.039 (14)0.05 (2)0.004 (15)0.003 (14)0.022 (15)
C24'0.034 (9)0.042 (8)0.049 (9)0.002 (7)0.004 (8)0.021 (6)
C25'0.038 (13)0.049 (12)0.049 (9)0.005 (9)0.000 (9)0.022 (8)
C260.040 (4)0.076 (4)0.060 (4)0.005 (3)0.003 (3)0.048 (3)
C270.036 (3)0.043 (3)0.047 (3)0.001 (3)0.006 (3)0.024 (3)
C280.028 (3)0.043 (3)0.046 (3)0.012 (3)0.006 (3)0.022 (3)
C290.036 (3)0.033 (3)0.054 (3)0.011 (3)0.015 (3)0.025 (3)
C300.036 (3)0.026 (3)0.060 (4)0.003 (2)0.006 (3)0.014 (3)
C310.039 (3)0.039 (3)0.050 (3)0.008 (3)0.009 (3)0.008 (3)
C320.045 (4)0.045 (3)0.044 (3)0.003 (3)0.001 (3)0.020 (3)
Geometric parameters (Å, º) top
Cu1—O41.890 (3)C8—C91.383 (7)
Cu1—N11.917 (4)C8—H8A0.9300
Cu1—O51.919 (3)C9—H90.9300
Cu1—O11.953 (3)C10—C111.441 (7)
Cu2—O91.896 (3)C10—H10A0.9300
Cu2—N21.909 (4)C11—C161.406 (7)
Cu2—O101.915 (3)C11—C121.422 (7)
Cu2—O61.946 (4)C12—C131.423 (7)
Cl1—C131.733 (5)C13—C141.366 (7)
Cl2—C151.756 (5)C14—C151.371 (7)
Cl3—C291.738 (5)C14—H140.9300
Cl4—C311.755 (5)C15—C161.374 (7)
N1—C101.278 (6)C16—H160.9300
N1—C21.463 (6)C17—C18'1.49 (2)
N2—C261.279 (6)C17—C181.56 (2)
N2—C18'1.47 (2)C18—C191.527 (17)
N2—C181.55 (2)C18—H180.9800
O1—C11.290 (6)C19—C201.50 (2)
O2—C11.229 (6)C19—H19A0.9700
O3—C71.361 (6)C19—H19B0.9700
O3—H30.8200C20—C211.38 (3)
O4—C121.301 (6)C20—C251.39 (3)
O5—H330.8499C21—C221.39 (3)
O5—H340.8498C21—H210.9300
O6—C171.285 (6)C22—C231.388 (18)
O7—C171.220 (6)C22—H220.9300
O8—C231.366 (14)C23—C241.38 (6)
O8—H80.8200C24—C251.39 (5)
O8'—C23'1.38 (7)C24—H240.9300
O8'—H8'0.8200C25—H250.9300
O9—C281.303 (6)C18'—C19'1.54 (2)
O10—H350.8500C18'—H18'0.9800
O10—H360.8500C19'—C20'1.499 (18)
O11—H370.8504C19'—H19C0.9700
O11—H380.8502C19'—H19D0.9700
O12—H390.8501C20'—C21'1.39 (2)
O12—H400.8501C20'—C25'1.39 (3)
O13—H410.8500C21'—C22'1.39 (2)
O13—H420.8500C21'—H21'0.9300
O12'—H39'0.8500C22'—C23'1.39 (4)
O12'—H40'0.8500C22'—H22'0.9300
O13'—H41'0.8500C23'—C24'1.39 (7)
O13'—H42'0.8500C24'—C25'1.39 (3)
C1—C21.543 (7)C24'—H24'0.9300
C2—C31.532 (7)C25'—H25'0.9300
C2—H20.9800C26—C271.442 (7)
C3—C41.494 (7)C26—H260.9300
C3—H3A0.9700C27—C321.401 (7)
C3—H3B0.9700C27—C281.423 (7)
C4—C91.392 (7)C28—C291.429 (7)
C4—C51.395 (7)C29—C301.358 (7)
C5—C61.368 (7)C30—C311.389 (7)
C5—H5A0.9300C30—H300.9300
C6—C71.379 (7)C31—C321.354 (7)
C6—H60.9300C32—H320.9300
C7—C81.379 (7)
O4—Cu1—N194.31 (16)C15—C16—H16119.7
O4—Cu1—O588.98 (15)C11—C16—H16119.7
N1—Cu1—O5176.21 (16)O7—C17—O6125.8 (5)
O4—Cu1—O1174.80 (15)O7—C17—C18'116.7 (9)
N1—Cu1—O184.68 (15)O6—C17—C18'116.2 (9)
O5—Cu1—O191.87 (15)O7—C17—C18116.8 (9)
O9—Cu2—N294.16 (16)O6—C17—C18116.0 (9)
O9—Cu2—O1089.46 (15)C19—C18—N2118.3 (12)
N2—Cu2—O10174.82 (18)C19—C18—C17105.5 (12)
O9—Cu2—O6177.43 (15)N2—C18—C17102.0 (11)
N2—Cu2—O683.96 (16)C19—C18—H18110.2
O10—Cu2—O692.31 (15)N2—C18—H18110.2
C10—N1—C2120.7 (4)C17—C18—H18110.2
C10—N1—Cu1125.7 (3)C20—C19—C18118.6 (13)
C2—N1—Cu1113.5 (3)C20—C19—H19A107.7
C26—N2—C18'118.4 (9)C18—C19—H19A107.7
C26—N2—C18120.1 (8)C20—C19—H19B107.7
C26—N2—Cu2126.6 (4)C18—C19—H19B107.7
C18'—N2—Cu2112.6 (8)H19A—C19—H19B107.1
C18—N2—Cu2112.7 (8)C21—C20—C25117.7 (17)
C1—O1—Cu1114.9 (3)C21—C20—C19122.2 (17)
C7—O3—H3109.5C25—C20—C19120.0 (17)
C12—O4—Cu1127.0 (3)C20—C21—C22120.7 (17)
Cu1—O5—H33124.3C20—C21—H21119.6
Cu1—O5—H34126.9C22—C21—H21119.6
H33—O5—H34107.4C23—C22—C21121.1 (14)
C17—O6—Cu2115.6 (3)C23—C22—H22119.5
C23'—O8'—H8'109.5C21—C22—H22119.5
C28—O9—Cu2126.2 (3)O8—C23—C24123 (3)
Cu2—O10—H35124.6O8—C23—C22118.9 (12)
Cu2—O10—H36130.1C24—C23—C22118 (3)
H35—O10—H36105.1C23—C24—C25121 (6)
H39—O12—H40103.0C23—C24—H24119.4
H41—O13—H42108.7C25—C24—H24119.4
H39'—O12'—H40'105.2C24—C25—C20121 (4)
H41'—O13'—H42'106.2C24—C25—H25119.4
O2—C1—O1124.1 (5)C20—C25—H25119.4
O2—C1—C2119.7 (5)N2—C18'—C17109.7 (13)
O1—C1—C2116.0 (5)N2—C18'—C19'107.5 (12)
N1—C2—C3112.2 (4)C17—C18'—C19'113.0 (13)
N1—C2—C1108.1 (4)N2—C18'—H18'108.8
C3—C2—C1106.6 (4)C17—C18'—H18'108.8
N1—C2—H2109.9C19'—C18'—H18'108.8
C3—C2—H2109.9C20'—C19'—C18'116.6 (12)
C1—C2—H2109.9C20'—C19'—H19C108.1
C4—C3—C2114.6 (4)C18'—C19'—H19C108.1
C4—C3—H3A108.6C20'—C19'—H19D108.1
C2—C3—H3A108.6C18'—C19'—H19D108.1
C4—C3—H3B108.6H19C—C19'—H19D107.3
C2—C3—H3B108.6C21'—C20'—C25'115.3 (15)
H3A—C3—H3B107.6C21'—C20'—C19'122.7 (14)
C9—C4—C5116.4 (5)C25'—C20'—C19'122.0 (16)
C9—C4—C3122.0 (5)C20'—C21'—C22'122.1 (14)
C5—C4—C3121.5 (5)C20'—C21'—H21'119.0
C6—C5—C4121.7 (5)C22'—C21'—H21'119.0
C6—C5—H5A119.2C23'—C22'—C21'120 (3)
C4—C5—H5A119.2C23'—C22'—H22'120.2
C5—C6—C7120.6 (5)C21'—C22'—H22'120.2
C5—C6—H6119.7O8'—C23'—C22'117 (5)
C7—C6—H6119.7O8'—C23'—C24'122 (3)
O3—C7—C8122.3 (5)C22'—C23'—C24'121 (5)
O3—C7—C6118.2 (5)C25'—C24'—C23'116 (3)
C8—C7—C6119.6 (5)C25'—C24'—H24'122.0
C7—C8—C9119.2 (5)C23'—C24'—H24'122.0
C7—C8—H8A120.4C24'—C25'—C20'125.8 (19)
C9—C8—H8A120.4C24'—C25'—H25'117.1
C8—C9—C4122.4 (5)C20'—C25'—H25'117.1
C8—C9—H9118.8N2—C26—C27125.2 (5)
C4—C9—H9118.8N2—C26—H26117.4
N1—C10—C11125.7 (5)C27—C26—H26117.4
N1—C10—H10A117.2C32—C27—C28120.9 (5)
C11—C10—H10A117.2C32—C27—C26117.3 (5)
C16—C11—C12120.5 (5)C28—C27—C26121.7 (5)
C16—C11—C10117.2 (5)O9—C28—C27125.5 (5)
C12—C11—C10122.3 (5)O9—C28—C29119.9 (4)
O4—C12—C11124.6 (5)C27—C28—C29114.5 (5)
O4—C12—C13120.0 (5)C30—C29—C28123.9 (5)
C11—C12—C13115.4 (5)C30—C29—Cl3118.6 (4)
C14—C13—C12123.4 (5)C28—C29—Cl3117.6 (4)
C14—C13—Cl1119.0 (4)C29—C30—C31119.0 (5)
C12—C13—Cl1117.7 (4)C29—C30—H30120.5
C13—C14—C15119.7 (5)C31—C30—H30120.5
C13—C14—H14120.2C32—C31—C30120.7 (5)
C15—C14—H14120.2C32—C31—Cl4121.0 (4)
C14—C15—C16120.6 (5)C30—C31—Cl4118.2 (4)
C14—C15—Cl2119.1 (4)C31—C32—C27120.9 (5)
C16—C15—Cl2120.3 (4)C31—C32—H32119.6
C15—C16—C11120.5 (5)C27—C32—H32119.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O12i0.821.882.643 (10)154
O8—H8···O7ii0.821.702.515 (9)175
O5—H33···O6iii0.851.892.714 (6)164
O13—H42···Cl1iv0.852.773.555 (9)154
C26—H26···O3v0.932.443.365 (7)173
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x+1, y, z+1; (v) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C16H11Cl2NO4)(H2O)]·1.5H2O
Mr460.74
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.006 (2), 13.899 (2), 14.565 (2)
α, β, γ (°)70.469 (2), 87.427 (3), 73.121 (3)
V3)1823.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.53
Crystal size (mm)0.40 × 0.18 × 0.09
Data collection
DiffractometerBruker SMART 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.580, 0.875
No. of measured, independent and
observed [I > 2σ(I)] reflections
9183, 6315, 3605
Rint0.027
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.143, 1.02
No. of reflections6315
No. of parameters583
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.36

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O12i0.821.882.643 (10)154
O8—H8···O7ii0.821.702.515 (9)175
O5—H33···O6iii0.851.892.714 (6)164
O13—H42···Cl1iv0.852.773.555 (9)154
C26—H26···O3v0.932.443.365 (7)173
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x+1, y, z+1; (v) x+1, y+1, z+1.
 

Acknowledgements

We acknowledge financial support by the Key Laboratory of Non-ferrous Metal Materials and New Processing Technology, Ministry of Education, P. R. China and the Creative Talents Base of Graduate Education, Guang Xi province.

References

First citationBruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCasella, L. & Gullotti, M. (1986). Inorg. Chem. 25, 1293–1303.  CrossRef CAS Web of Science Google Scholar
First citationGuthrie, J. W., Lintvedt, R. L. & Glick, M. D. (1980). Inorg. Chem. 19, 2949–2955.  CSD CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, Z., Wu, Z., Yen, Z., Le, Z., Zhu, X. & Huang, Q. (1994). Synth. React. Inorg. Met.-Org. Chem. 24, 1453–1460.  Google Scholar
First citationZhang, S. H., Jiang, Y. M., Xiao, Y. & Zhou, Z. Y. (2003). Chin. J. Inorg. Chem. 19, 517–520.  CAS Google Scholar

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