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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m953.
Published online 2008 June 21. doi:  10.1107/S1600536808018357
PMCID: PMC2961693

μ-4,4′-Bipyridine-κ2 N:N′-bis­{[2-(3,5-dibromo-2-oxidobenzyl­ideneamino)-3-hydroxy­propanoato-κ3 O,N,O′]copper(II)} monohydrate

Abstract

The title compound, [Cu2(C10H7Br2NO4)2(C10H8N2)]·H2O, is a binuclear copper(II) complex. Both Cu atoms are four-coordinate in a square-planar geometry. In addition, there is one water mol­ecule in the asymmetric unit. The crystal structure is stabilized by O—H(...)O and O—H(...)Br hydrogen bonds.

Related literature

For related literature, see: Gao et al. (2005 [triangle]); Liang et al. (2006 [triangle]); Zhang et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m953-scheme1.jpg

Experimental

Crystal data

  • [Cu2(C10H7Br2NO4)2(C10H8N2)]·H2O
  • M r = 1031.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m953-efi1.jpg
  • a = 7.3905 (7) Å
  • b = 11.3374 (16) Å
  • c = 19.943 (2) Å
  • β = 93.686 (2)°
  • V = 1667.6 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 6.13 mm−1
  • T = 298 (2) K
  • 0.18 × 0.17 × 0.16 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.405, T max = 0.441 (expected range = 0.345–0.375)
  • 8428 measured reflections
  • 5732 independent reflections
  • 3029 reflections with I > 2σ(I)
  • R int = 0.084

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073
  • wR(F 2) = 0.187
  • S = 1.02
  • 5732 reflections
  • 442 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.73 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 5732 Friedel pairs
  • Flack parameter: 0.00 (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/S1600536808018357/bt2726sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018357/bt2726Isup2.hkl

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

Acknowledgments

We acknowledge financial support by the Key Laboratory of Non-ferrous Metal Materials andProcessing Technology, Ministry of Education, People’s Republic of China.

supplementary crystallographic information

Comment

Amino acids are the basic unit of proteins and enzymes, and they can form a series of amino acid Schiff-bases. Even though considerable work has been done on the complexes of amino acid Schiff-bases (Zhang et al., 2003; Liang et al., 2006; Gao et al., 2005), there is not much reported on amino acid Schiff-base complexes containing 4,4'-bipyridine as an additional ligand.

The coordination environment of Cu1 and Cu2 is almost equal, so we choose Cu1 for discussion. The distance of Cu1—N1 is 1.932 (16)Å, and the distance Cu1—N3 is 2.038 (14)Å. The bond angle of four atoms coordinated with Cu1 ion are as follows: O4—Cu1—N1 = 93.2 (6)°, N1—Cu1—O1 = 83.7 (6)°, O1—Cu1—N3 = 92.7 (6)°, N3—Cu1—O4 = 90.5 (6)°. The mean deviation from plane of the four atoms coordinated to Cu1 is 0.0507 Å, showing that these four atoms lie in a common plane. The packing didagram (Fig.2) shows that the water molecules is connected to the complex through H–O···Br hydrogen bonds. In addition, there are O–H···O hydrogen bonds stabilizing the crystal structure.

Experimental

An ethanol solution (5 ml) containing 3,5-dibromo-2-hydroxy-benzaldehyde (0.140 g, 0.5 mmol) was added to an aqueous solution (5 ml) containing 2-amino-3-hydroxy-propionic acid (0.056 g, 0.5 mmol) and sodium hydroxide (0.040 g, 1 mmol). After stirring for 1 h, an aqueous solution of copper nitrate (0.120 g, 0.5 mmol) was added to the resulting solution and stirred for 2 h. At last, the ethanol solution (5 ml) containing 4, 4'-bipyridine (0.05 g, 0.025 mmol) was added. The green solution was filtrated. After five days, green block shaped crystals were obtained by slow evaporation of the filtrate (yield: 36.5%, 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 atomswere 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 (I), showing 30% probability displacement ellipsoids.
Fig. 2.
The three-dimensional network of (I) through hydrogen bonds.

Crystal data

[Cu2(C10H7Br2N1O4)2(C10H8N2)]·H2OF000 = 1004
Mr = 1031.25Dx = 2.054 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1685 reflections
a = 7.3905 (7) Åθ = 2.7–24.9º
b = 11.3374 (16) ŵ = 6.13 mm1
c = 19.943 (2) ÅT = 298 (2) K
β = 93.686 (2)ºBlock, green
V = 1667.6 (3) Å30.18 × 0.17 × 0.16 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer5732 independent reflections
Radiation source: fine-focus sealed tube3029 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.084
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −5→8
Tmin = 0.405, Tmax = 0.441k = −13→13
8428 measured reflectionsl = −23→23

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.073  w = 1/[σ2(Fo2) + (0.0693P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.187(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.80 e Å3
5732 reflectionsΔρmin = −0.73 e Å3
442 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 2625 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.00 (3)
Secondary atom site location: difference Fourier map

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 (Å2)

xyzUiso*/Ueq
Cu10.6425 (3)0.82294 (19)0.68048 (12)0.0410 (6)
Cu20.3052 (3)−0.0991 (2)0.82661 (12)0.0400 (6)
Br10.8208 (3)0.8393 (2)0.91853 (11)0.0580 (6)
Br21.0514 (3)1.3118 (2)0.88646 (14)0.0752 (8)
Br30.1238 (3)−0.11439 (18)0.58941 (10)0.0531 (6)
Br4−0.0792 (3)−0.5930 (2)0.61848 (12)0.0656 (7)
N10.678 (2)0.9816 (14)0.6484 (8)0.042 (4)
N20.251 (2)−0.2541 (14)0.8606 (8)0.042 (4)
N30.589 (2)0.6542 (12)0.7086 (8)0.037 (4)
N40.3702 (19)0.0648 (13)0.7989 (8)0.036 (4)
O10.5913 (18)0.7883 (11)0.5864 (7)0.047 (4)
O20.558 (2)0.8659 (13)0.4829 (7)0.067 (5)
O30.724 (2)1.1969 (14)0.5553 (8)0.081 (5)
H30.63321.23290.54140.122*
O40.7108 (17)0.8640 (11)0.7719 (6)0.049 (4)
O50.3548 (17)−0.0627 (10)0.9202 (6)0.043 (4)
O60.3950 (19)−0.1389 (12)1.0224 (6)0.055 (4)
O70.3448 (19)−0.4755 (12)0.9412 (8)0.068 (4)
H70.4236−0.52640.94470.102*
O80.2331 (17)−0.1390 (10)0.7358 (7)0.046 (4)
O90.820 (2)0.6748 (12)0.4525 (8)0.095 (5)
H9A0.84380.60550.43910.114*
H9B0.88770.72330.43320.114*
C10.578 (3)0.8763 (19)0.5442 (11)0.053 (5)
C20.612 (3)0.9974 (17)0.5764 (10)0.048 (5)
H20.49111.03260.57800.058*
C30.714 (3)1.0800 (16)0.5322 (10)0.057 (6)
H3A0.83621.05010.52920.068*
H3B0.65531.07940.48730.068*
C40.759 (3)1.0674 (17)0.6838 (10)0.047 (5)
H40.77621.13870.66190.056*
C50.821 (3)1.0595 (17)0.7508 (10)0.044 (5)
C60.793 (3)0.9601 (18)0.7942 (11)0.043 (5)
C70.853 (3)0.9737 (18)0.8614 (11)0.050 (6)
C80.928 (3)1.0682 (19)0.8908 (11)0.049 (6)
H80.96111.06990.93650.059*
C90.954 (3)1.1678 (18)0.8481 (11)0.048 (6)
C100.900 (3)1.1637 (19)0.7819 (11)0.049 (5)
H100.91401.23050.75570.058*
C110.351 (2)−0.1498 (17)0.9624 (10)0.043 (5)
C120.282 (3)−0.2650 (16)0.9346 (10)0.044 (5)
H120.1672−0.28410.95400.053*
C130.424 (3)−0.3636 (15)0.9540 (10)0.050 (5)
H13A0.5294−0.35430.92800.060*
H13B0.4629−0.35701.00130.060*
C140.171 (2)−0.3387 (17)0.8278 (10)0.040 (5)
H140.1344−0.40350.85210.048*
C150.132 (3)−0.3404 (17)0.7536 (10)0.041 (5)
C160.155 (3)−0.2372 (17)0.7129 (11)0.041 (5)
C170.100 (2)−0.2486 (17)0.6457 (10)0.039 (5)
C180.029 (2)−0.3534 (17)0.6184 (11)0.046 (5)
H18−0.0080−0.35680.57290.055*
C190.013 (3)−0.4503 (17)0.6576 (11)0.044 (5)
C200.056 (2)−0.4448 (17)0.7274 (10)0.043 (5)
H200.0349−0.50860.75510.051*
C210.520 (3)0.5759 (16)0.6625 (10)0.039 (5)
H210.50160.60080.61810.047*
C220.477 (2)0.4650 (16)0.6773 (10)0.038 (5)
H220.42470.41620.64390.046*
C230.509 (2)0.4221 (15)0.7418 (9)0.034 (4)
C240.579 (2)0.4999 (16)0.7890 (10)0.040 (5)
H240.60180.47580.83330.048*
C250.618 (3)0.6195 (16)0.7698 (10)0.041 (5)
H250.66420.67240.80220.049*
C260.331 (3)0.1090 (16)0.7361 (10)0.041 (5)
H260.27290.05860.70480.050*
C270.368 (2)0.2229 (16)0.7147 (10)0.040 (5)
H270.33770.24720.67090.048*
C280.454 (2)0.2985 (16)0.7613 (9)0.039 (5)
C290.498 (2)0.2568 (16)0.8271 (10)0.039 (5)
H290.55700.30580.85890.047*
C300.452 (2)0.1379 (16)0.8441 (10)0.041 (5)
H300.48010.11100.88760.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0588 (15)0.0261 (13)0.0369 (14)−0.0032 (12)−0.0069 (12)0.0037 (12)
Cu20.0560 (14)0.0274 (13)0.0353 (14)−0.0029 (12)−0.0063 (11)0.0035 (12)
Br10.0639 (13)0.0598 (15)0.0494 (14)0.0004 (11)−0.0033 (10)0.0105 (12)
Br20.0904 (18)0.0616 (18)0.0719 (17)−0.0270 (15)−0.0074 (13)−0.0250 (16)
Br30.0715 (14)0.0456 (13)0.0410 (13)−0.0020 (11)−0.0063 (10)0.0104 (10)
Br40.0863 (16)0.0439 (14)0.0649 (16)−0.0157 (13)−0.0071 (12)−0.0127 (14)
N10.054 (10)0.032 (10)0.038 (10)−0.005 (8)−0.008 (8)−0.004 (8)
N20.058 (11)0.027 (9)0.039 (11)0.003 (8)−0.003 (8)0.007 (8)
N30.059 (10)0.020 (8)0.030 (10)0.000 (7)−0.004 (8)0.006 (8)
N40.047 (10)0.029 (9)0.032 (10)−0.006 (7)0.007 (8)−0.005 (8)
O10.070 (10)0.027 (8)0.044 (9)−0.004 (6)−0.007 (7)0.003 (7)
O20.110 (11)0.052 (12)0.037 (9)−0.016 (8)−0.009 (8)0.000 (8)
O30.103 (12)0.052 (10)0.087 (13)−0.017 (9)−0.015 (10)0.004 (10)
O40.070 (9)0.030 (8)0.044 (8)−0.005 (6)−0.012 (7)−0.003 (6)
O50.065 (9)0.027 (8)0.037 (8)−0.004 (6)−0.007 (7)0.001 (6)
O60.106 (11)0.039 (10)0.020 (8)−0.005 (7)−0.001 (7)0.004 (6)
O70.097 (12)0.032 (8)0.069 (11)−0.011 (7)−0.033 (8)0.018 (8)
O80.064 (9)0.026 (8)0.046 (8)−0.009 (6)−0.003 (7)0.003 (6)
O90.136 (15)0.049 (9)0.099 (13)−0.016 (9)−0.004 (11)−0.008 (8)
C10.072 (14)0.037 (13)0.047 (13)−0.004 (10)−0.009 (11)−0.005 (12)
C20.067 (14)0.039 (12)0.038 (12)−0.005 (10)−0.010 (11)−0.003 (10)
C30.073 (15)0.043 (12)0.052 (14)−0.009 (11)−0.015 (11)0.006 (10)
C40.061 (14)0.035 (12)0.044 (13)−0.005 (10)−0.004 (11)−0.008 (10)
C50.059 (14)0.035 (12)0.038 (13)−0.003 (9)−0.009 (10)−0.013 (10)
C60.055 (13)0.033 (12)0.040 (13)0.002 (9)−0.011 (10)−0.005 (10)
C70.060 (14)0.041 (13)0.046 (14)0.006 (10)−0.012 (11)−0.008 (11)
C80.056 (14)0.043 (13)0.047 (14)0.008 (10)−0.018 (11)−0.013 (11)
C90.057 (14)0.038 (13)0.048 (14)0.006 (9)−0.014 (11)−0.017 (11)
C100.060 (14)0.040 (12)0.045 (14)0.001 (10)−0.004 (11)−0.006 (11)
C110.063 (13)0.030 (12)0.035 (11)−0.004 (9)−0.016 (9)0.005 (10)
C120.061 (13)0.032 (11)0.037 (12)−0.004 (9)−0.011 (10)0.006 (9)
C130.076 (15)0.031 (11)0.041 (12)0.000 (10)−0.013 (11)0.005 (9)
C140.047 (12)0.031 (11)0.043 (13)0.000 (9)−0.001 (10)0.009 (10)
C150.045 (12)0.034 (12)0.042 (13)0.002 (9)0.004 (10)0.004 (10)
C160.045 (12)0.032 (12)0.046 (14)0.004 (9)−0.001 (10)−0.001 (10)
C170.039 (11)0.035 (12)0.041 (13)0.004 (8)−0.004 (9)0.005 (10)
C180.053 (13)0.042 (13)0.042 (13)−0.003 (10)−0.001 (11)−0.007 (10)
C190.048 (12)0.036 (12)0.047 (14)0.001 (9)0.003 (10)−0.004 (11)
C200.049 (12)0.031 (12)0.047 (14)0.004 (9)−0.003 (10)0.002 (10)
C210.057 (13)0.031 (12)0.029 (11)0.002 (9)0.002 (10)0.006 (9)
C220.055 (12)0.024 (11)0.034 (13)−0.003 (9)−0.010 (9)0.005 (9)
C230.050 (11)0.023 (11)0.028 (11)0.000 (8)−0.005 (9)0.000 (9)
C240.057 (13)0.028 (12)0.035 (12)−0.001 (9)−0.003 (10)0.009 (9)
C250.057 (13)0.032 (11)0.032 (12)0.004 (9)0.000 (10)0.003 (9)
C260.056 (13)0.031 (11)0.037 (13)−0.010 (9)−0.001 (10)−0.001 (10)
C270.056 (13)0.032 (12)0.032 (12)0.001 (9)−0.002 (10)0.002 (9)
C280.053 (12)0.027 (12)0.035 (12)0.001 (9)−0.002 (10)0.000 (10)
C290.055 (13)0.028 (12)0.033 (13)−0.003 (9)−0.012 (9)−0.002 (9)
C300.057 (13)0.036 (12)0.031 (12)−0.006 (9)−0.004 (10)0.001 (9)

Geometric parameters (Å, °)

Cu1—O41.917 (13)C5—C61.44 (3)
Cu1—O11.930 (13)C6—C71.39 (3)
Cu1—N11.932 (16)C7—C81.32 (3)
Cu1—N32.038 (14)C8—C91.44 (3)
Cu2—O81.909 (13)C8—H80.9300
Cu2—O51.924 (13)C9—C101.36 (3)
Cu2—N21.934 (16)C10—H100.9300
Cu2—N42.006 (15)C11—C121.50 (3)
Br1—C71.93 (2)C12—C131.56 (2)
Br2—C91.92 (2)C12—H120.9800
Br3—C171.905 (19)C13—H13A0.9700
Br4—C191.90 (2)C13—H13B0.9700
N1—C41.32 (2)C14—C151.49 (3)
N1—C21.50 (2)C14—H140.9300
N2—C141.28 (2)C15—C201.40 (3)
N2—C121.48 (2)C15—C161.44 (3)
N3—C251.29 (2)C16—C171.38 (3)
N3—C211.36 (2)C17—C181.40 (3)
N4—C301.34 (2)C18—C191.36 (3)
N4—C261.36 (2)C18—H180.9300
O1—C11.30 (2)C19—C201.41 (3)
O2—C11.23 (2)C20—H200.9300
O3—C31.40 (2)C21—C221.34 (2)
O3—H30.8200C21—H210.9300
O4—C61.31 (2)C22—C231.38 (2)
O5—C111.30 (2)C22—H220.9300
O6—C111.23 (2)C23—C241.37 (2)
O7—C131.41 (2)C23—C281.517 (18)
O7—H70.8200C24—C251.44 (2)
O8—C161.32 (2)C24—H240.9300
O9—H9A0.8500C25—H250.9300
O9—H9B0.8500C26—C271.39 (2)
C1—C21.53 (3)C26—H260.9300
C2—C31.52 (3)C27—C281.39 (2)
C2—H20.9800C27—H270.9300
C3—H3A0.9700C28—C291.41 (2)
C3—H3B0.9700C29—C301.44 (2)
C4—C51.39 (3)C29—H290.9300
C4—H40.9300C30—H300.9300
C5—C101.44 (3)
O4—Cu1—O1175.3 (6)O6—C11—O5122.7 (18)
O4—Cu1—N193.2 (6)O6—C11—C12120.8 (18)
O1—Cu1—N183.7 (6)O5—C11—C12116.4 (16)
O4—Cu1—N390.5 (6)N2—C12—C11108.8 (15)
O1—Cu1—N392.7 (6)N2—C12—C13111.3 (16)
N1—Cu1—N3175.6 (6)C11—C12—C13109.1 (15)
O8—Cu2—O5174.5 (6)N2—C12—H12109.2
O8—Cu2—N293.8 (6)C11—C12—H12109.2
O5—Cu2—N283.4 (6)C13—C12—H12109.2
O8—Cu2—N490.9 (6)O7—C13—C12109.5 (15)
O5—Cu2—N492.0 (6)O7—C13—H13A109.8
N2—Cu2—N4175.3 (7)C12—C13—H13A109.8
C4—N1—C2122.1 (17)O7—C13—H13B109.8
C4—N1—Cu1125.1 (14)C12—C13—H13B109.8
C2—N1—Cu1112.7 (12)H13A—C13—H13B108.2
C14—N2—C12118.8 (16)N2—C14—C15124.7 (18)
C14—N2—Cu2126.8 (14)N2—C14—H14117.7
C12—N2—Cu2113.7 (12)C15—C14—H14117.7
C25—N3—C21118.4 (16)C20—C15—C16122.5 (18)
C25—N3—Cu1121.7 (13)C20—C15—C14115.4 (18)
C21—N3—Cu1119.9 (12)C16—C15—C14121.8 (18)
C30—N4—C26116.9 (16)O8—C16—C17120.6 (19)
C30—N4—Cu2119.5 (12)O8—C16—C15123.6 (19)
C26—N4—Cu2123.5 (12)C17—C16—C15115.6 (18)
C1—O1—Cu1118.3 (12)C16—C17—C18122.6 (19)
C3—O3—H3109.5C16—C17—Br3117.7 (15)
C6—O4—Cu1127.8 (13)C18—C17—Br3119.7 (16)
C11—O5—Cu2117.1 (11)C19—C18—C17120 (2)
C13—O7—H7109.5C19—C18—H18119.8
C16—O8—Cu2128.1 (13)C17—C18—H18119.8
H9A—O9—H9B108.6C18—C19—C20120.7 (19)
O2—C1—O1124.7 (19)C18—C19—Br4119.5 (16)
O2—C1—C2121 (2)C20—C19—Br4119.7 (15)
O1—C1—C2114.4 (17)C15—C20—C19117.8 (19)
N1—C2—C3119.0 (17)C15—C20—H20121.1
N1—C2—C1109.2 (17)C19—C20—H20121.1
C3—C2—C1112.6 (17)C22—C21—N3123.6 (18)
N1—C2—H2104.9C22—C21—H21118.2
C3—C2—H2104.9N3—C21—H21118.2
C1—C2—H2104.9C21—C22—C23120.5 (19)
O3—C3—C2114.2 (17)C21—C22—H22119.7
O3—C3—H3A108.7C23—C22—H22119.7
C2—C3—H3A108.7C24—C23—C22116.7 (17)
O3—C3—H3B108.7C24—C23—C28121.0 (14)
C2—C3—H3B108.7C22—C23—C28122.1 (14)
H3A—C3—H3B107.6C23—C24—C25119.8 (18)
N1—C4—C5125.1 (19)C23—C24—H24120.1
N1—C4—H4117.5C25—C24—H24120.1
C5—C4—H4117.5N3—C25—C24121.1 (18)
C4—C5—C10117.4 (19)N3—C25—H25119.5
C4—C5—C6125.4 (19)C24—C25—H25119.5
C10—C5—C6116.7 (18)N4—C26—C27125.9 (18)
O4—C6—C7122 (2)N4—C26—H26117.1
O4—C6—C5121.6 (18)C27—C26—H26117.1
C7—C6—C5116.3 (18)C28—C27—C26117.3 (19)
C8—C7—C6128 (2)C28—C27—H27121.4
C8—C7—Br1116.2 (16)C26—C27—H27121.4
C6—C7—Br1116.0 (15)C27—C28—C29119.0 (18)
C7—C8—C9116 (2)C27—C28—C23121.1 (14)
C7—C8—H8121.9C29—C28—C23119.8 (14)
C9—C8—H8121.9C28—C29—C30119.3 (18)
C10—C9—C8121 (2)C28—C29—H29120.4
C10—C9—Br2119.8 (17)C30—C29—H29120.4
C8—C9—Br2119.6 (15)N4—C30—C29121.6 (18)
C9—C10—C5122 (2)N4—C30—H30119.2
C9—C10—H10118.9C29—C30—H30119.2
C5—C10—H10118.9
O4—Cu1—N1—C411.7 (16)Cu2—O5—C11—C12−9(2)
O1—Cu1—N1—C4−164.7 (16)C14—N2—C12—C11−171.5 (16)
O4—Cu1—N1—C2−171.5 (13)Cu2—N2—C12—C11−1(2)
O1—Cu1—N1—C212.0 (13)C14—N2—C12—C1368 (2)
O8—Cu2—N2—C14−8.0 (17)Cu2—N2—C12—C13−121.0 (14)
O5—Cu2—N2—C14167.2 (17)O6—C11—C12—N2−176.3 (17)
O8—Cu2—N2—C12−177.9 (13)O5—C11—C12—N26(3)
O5—Cu2—N2—C12−2.7 (12)O6—C11—C12—C13−55 (3)
O4—Cu1—N3—C25−3.0 (15)O5—C11—C12—C13127.6 (17)
O1—Cu1—N3—C25173.6 (14)N2—C12—C13—O7−73 (2)
O4—Cu1—N3—C21176.1 (14)C11—C12—C13—O7167.3 (17)
O1—Cu1—N3—C21−7.3 (14)C12—N2—C14—C15−179.4 (17)
O8—Cu2—N4—C30−173.2 (13)Cu2—N2—C14—C1511 (3)
O5—Cu2—N4—C3011.5 (14)N2—C14—C15—C20175.3 (17)
O8—Cu2—N4—C268.9 (15)N2—C14—C15—C16−11 (3)
O5—Cu2—N4—C26−166.4 (15)Cu2—O8—C16—C17175.6 (13)
N1—Cu1—O1—C1−8.0 (14)Cu2—O8—C16—C15−9(3)
N3—Cu1—O1—C1169.3 (14)C20—C15—C16—O8−177.2 (17)
N1—Cu1—O4—C6−14.4 (16)C14—C15—C16—O89(3)
N3—Cu1—O4—C6168.0 (15)C20—C15—C16—C17−1(3)
N2—Cu2—O5—C116.4 (13)C14—C15—C16—C17−174.9 (17)
N4—Cu2—O5—C11−172.7 (13)O8—C16—C17—C18175.4 (17)
N2—Cu2—O8—C166.8 (15)C15—C16—C17—C18−1(3)
N4—Cu2—O8—C16−173.8 (15)O8—C16—C17—Br3−5(2)
Cu1—O1—C1—O2174.8 (16)C15—C16—C17—Br3179.1 (13)
Cu1—O1—C1—C22(2)C16—C17—C18—C19−1(3)
C4—N1—C2—C332 (3)Br3—C17—C18—C19179.2 (14)
Cu1—N1—C2—C3−145.0 (15)C17—C18—C19—C205(3)
C4—N1—C2—C1163.1 (17)C17—C18—C19—Br4−178.5 (14)
Cu1—N1—C2—C1−14 (2)C16—C15—C20—C195(3)
O2—C1—C2—N1−165.5 (18)C14—C15—C20—C19178.6 (16)
O1—C1—C2—N18(2)C18—C19—C20—C15−6(3)
O2—C1—C2—C3−31 (3)Br4—C19—C20—C15176.9 (14)
O1—C1—C2—C3142.5 (19)C25—N3—C21—C221(3)
N1—C2—C3—O3−59 (3)Cu1—N3—C21—C22−178.0 (15)
C1—C2—C3—O3171.1 (17)N3—C21—C22—C23−3(3)
C2—N1—C4—C5178.9 (19)C21—C22—C23—C242(3)
Cu1—N1—C4—C5−5(3)C21—C22—C23—C28177.2 (16)
N1—C4—C5—C10−177.6 (18)C22—C23—C24—C25−1(3)
N1—C4—C5—C6−5(3)C28—C23—C24—C25−175.5 (15)
Cu1—O4—C6—C7−172.9 (14)C21—N3—C25—C241(3)
Cu1—O4—C6—C510 (3)Cu1—N3—C25—C24179.8 (13)
C4—C5—C6—O43(3)C23—C24—C25—N3−1(3)
C10—C5—C6—O4175.2 (17)C30—N4—C26—C270(3)
C4—C5—C6—C7−174.8 (19)Cu2—N4—C26—C27178.3 (14)
C10—C5—C6—C7−2(3)N4—C26—C27—C280(3)
C5—C6—C7—C82(3)C26—C27—C28—C290(3)
O4—C6—C7—Br14(3)C26—C27—C28—C23177.0 (15)
C5—C6—C7—Br1−178.7 (14)C24—C23—C28—C27174.5 (19)
C6—C7—C8—C9−1(3)C22—C23—C28—C270(2)
Br1—C7—C8—C9179.1 (14)C24—C23—C28—C29−9(2)
C7—C8—C9—C102(3)C22—C23—C28—C29176.6 (19)
C7—C8—C9—Br2177.2 (15)C27—C28—C29—C30−1(3)
C8—C9—C10—C5−3(3)C23—C28—C29—C30−177.4 (16)
Br2—C9—C10—C5−178.0 (15)C26—N4—C30—C29−1(3)
C4—C5—C10—C9175.9 (19)Cu2—N4—C30—C29−178.8 (14)
C6—C5—C10—C93(3)C28—C29—C30—N41(3)
Cu2—O5—C11—O6173.7 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.822.102.90 (2)164
O7—H7···O6ii0.821.932.73 (2)165
O9—H9A···Br3i0.852.573.415 (14)171
O9—H9B···Br4iii0.852.763.599 (15)171

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+2; (iii) −x+1, y+3/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2726).

References

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  • Liang, F. Z., Ma, J. P. & Zhu, J. H. (2006). Chin. J. Inorg. Chem.22, 115–118.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, S. H., Jiang, Y. M., Xiao, Y. & Zhou, Z. Y. (2003). Chin. J. Inorg. Chem.19, 517–520.

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