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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m756.
Published online 2008 May 3. doi:  10.1107/S1600536808012038
PMCID: PMC2961633

Aqua­{2-[(3,5-dichloro-2-oxidobenzyl­idene)amino]-3-(4-hydroxy­phen­yl)propionato-κ3 O 1,N,O 2}copper(II) sesquihydrate

Abstract

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 [triangle]); Guthrie et al. (1980 [triangle]); Wang et al. (1994 [triangle]); Zhang et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m756-scheme1.jpg

Experimental

Crystal data

  • [Cu(C16H11Cl2NO4)(H2O)]·1.5H2O
  • M r = 460.74
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m756-efi1.jpg
  • 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 [triangle]) T min = 0.580, T max = 0.875
  • 9183 measured reflections
  • 6315 independent reflections
  • 3605 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 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

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012038/cs2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012038/cs2072Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
A view of the title complex showing 30% probability displacement ellipsoids. H atoms, except for the water molecules, are not shown.
Fig. 2.
The disordered tyrosine view in one of the complexes.
Fig. 3.
The three-dimensional network of Cu···Cl weak interactions and hydrogen bonds shown in dotted lines.

Crystal data

[Cu(C16H11Cl2N1O4)(H2O1)]·1.5H2O1Z = 4
Mr = 460.74F000 = 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 = 2.3–25.2º
α = 70.469 (2)ºµ = 1.53 mm1
β = 87.427 (3)ºT = 293 (2) K
γ = 73.121 (3)ºPlate, green
V = 1823.8 (5) Å30.40 × 0.18 × 0.09 mm

Data collection

Bruker SMART 1000 diffractometer6315 independent reflections
Radiation source: fine-focus sealed tube3605 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 293(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.580, Tmax = 0.875k = −12→16
9183 measured reflectionsl = −16→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.143  w = 1/[σ2(Fo2) + (0.0669P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6315 reflectionsΔρmax = 0.58 e Å3
583 parametersΔρmin = −0.36 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Cu10.46267 (7)0.15476 (5)0.36588 (4)0.0406 (2)
Cu2−0.01499 (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*
O6−0.1909 (4)0.7570 (3)−0.1170 (3)0.0508 (10)
O7−0.3148 (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)
H8'0.49120.9095−0.06910.074*0.493 (5)
O90.1554 (3)0.5378 (3)−0.0977 (2)0.0459 (9)
O10−0.0682 (4)0.6254 (3)−0.2247 (2)0.0547 (10)
H35−0.12830.6714−0.26900.082*
H36−0.03570.5731−0.24520.082*
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)
H141.0306−0.17980.51580.052*
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*
C17−0.2082 (5)0.7943 (4)−0.0462 (4)0.0420 (13)
C18−0.073 (2)0.7774 (14)0.0135 (14)0.038 (4)0.507 (5)
H18−0.09320.77050.08140.045*0.507 (5)
C19−0.0263 (11)0.8773 (8)−0.0352 (8)0.045 (3)0.507 (5)
H19A−0.02560.8894−0.10470.053*0.507 (5)
H19B−0.09730.9373−0.02590.053*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)
H240.41770.8887−0.08340.053*0.507 (5)
C250.218 (2)0.8852 (13)−0.0675 (12)0.044 (4)0.507 (5)
H250.20230.8875−0.13070.053*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)
H19C−0.12740.88110.05980.046*0.493 (5)
H19D−0.02850.78450.14050.046*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)
H21'0.01390.8811−0.11670.048*0.493 (5)
C22'0.2054 (19)0.9017 (13)−0.1196 (11)0.042 (4)0.493 (5)
H22'0.21260.9191−0.18670.050*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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2072).

References

  • Bruker (2004). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Casella, L. & Gullotti, M. (1986). Inorg. Chem.25, 1293–1303.
  • Guthrie, J. W., Lintvedt, R. L. & Glick, M. D. (1980). Inorg. Chem.19, 2949–2955.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Z., Wu, Z., Yen, Z., Le, Z., Zhu, X. & Huang, Q. (1994). Synth. React. Inorg. Met.-Org. Chem.24, 1453–1460.
  • Zhang, S. H., Jiang, Y. M., Xiao, Y. & Zhou, Z. Y. (2003). Chin. J. Inorg. Chem.19, 517–520.

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