Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041517/er2034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041517/er2034Isup2.hkl |
CCDC reference: 667095
A solution of aspartic acid (0.059 g, 0.5 mmol) and pottasium hydroxide (0.028 g, 0.5 mmol) in distilled water (10 ml) was added slowly to a solution of 3,5-dibromo-2-hydroxybenzaldehyde (0.5 mmol, 0.140 g) in ethanol (10 ml). The mixture was stirred for 1 h at 323 K, then added slowly to a solution of copper(II) nitrate (0.121 g, 0.5 mmol) in distilled water (10 ml). This mixture was stirred and refluxed for 2 h at 323 K; The precipitate was separated by filtration. Dregs were dissolved in DMF. The solution was filtered and the filtrate was left to stand at room temperature. Blue strips suitable for X-ray diffraction were obtained in a yield of 65% (based on copper nitrate).
H atoms of the water molecule were located in a difference Fourier map. The O—H distances were normalized to 0.85 Å and the H atoms were allowed to ride on the O atom, with Uiso(H) = 1.5 Ueq(O). All other H atoms were positioned geometrically and refined as riding, with C—H distances of 0.93–0.98 Å and Uiso(H) = 1.2 Ueq(C) and with O—H distances of 0.82 Å and Uiso(H) = 1.5 Ueq(O).
Rencently, compounds containing dimmer water (Ghosh & Bharadwaj, 2003), water ring (Moorthy et al., 2002, Ugalde et al., 2000, Ghosh & Bharadwaj, 2004), water chain (Neogi & Bharadwaj, 2005, Cheruzel et al., 2003, Ghosh et al., 2005), metal-water chain (Ye et al., 2004), water network (Zhang et al., 2005), water-methanol intermix clusters (Raghuraman et al., 2003), and water ring chain (Feng, et al., 2007) give rise to considerable interest. Because these dimmer water, water ring, water chain, metal-water chain, water network, water ring chain and intermix clusters are potentially important form of water that is poorly understood. Water chains appear to facilitate the selective permeation (Tajkhorshid et al., 2002) of water across membranes and also to be important (Zaslavsky, & Gennis, 2000) in the control of proton fluxes in a variety of biomolecules.
The title compound, (I), is a CuII complex containing a ligand constructed from 2-(3,5-dibromo-2-hydroxy-benzylamino)-succinic acid and 3,5-dichloro-2-hydroxy-benzaldehyde. Each CuII atom is coordinated by two O atoms and one N atom from L2- and one O atom from DMF and one O atom from H2O to furnish a slightly distorted tetragonal pyramidal(Table 1). The asymmetric unit (Fig. 1) comprises one CuII complexes, one water molecule and one DMF molecule. The water molecules are linked by O—H···O hydrogen bonds (Table 2), forming a 'peral necklace' water chains. In the 'pearl necklace' water chains, the O8 water act as thread and the O9 water as pearl along 101 plan(Fig. 2). The water chains lie between layers of CuII complexes (Fig. 3), forming O—H···O hydrogen bonds to the O2 atoms of the carboxylate groups. The complex are further constructed three-dimensional supramolecular network through O—H···O hydrogen bond and C—H···Br hydrogen bond (Fig. 3).
For related literature, see: Cheruzel et al. (2003); Feng et al. (2007); Ghosh & Bharadwaj (2003); Ghosh & Bharadwaj (2004); Ghosh et al. (2005); Moorthy et al. (2002); Neogi & Bharadwaj (2005); Raghuraman et al. (2003); Tajkhorshid et al. (2002); Ugalde et al. (2000); Ye et al. (2004); Zaslavsky & Gennis (2000); Zhang et al. (2005).
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
[Cu(C11H7Br2NO5)(C3H7NO)(H2O)]·C3H7NO·H2O | F(000) = 2552 |
Mr = 638.76 | Dx = 1.820 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4147 reflections |
a = 46.176 (3) Å | θ = 2.7–25.7° |
b = 5.1633 (19) Å | µ = 4.42 mm−1 |
c = 21.793 (2) Å | T = 298 K |
β = 116.186 (4)° | Strip, blue |
V = 4662.6 (18) Å3 | 0.56 × 0.10 × 0.07 mm |
Z = 8 |
Bruker SMART 1K CCD diffractometer | 4091 independent reflections |
Radiation source: fine-focus sealed tube | 3197 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 10 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
φ and ω scans | h = −54→33 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −6→6 |
Tmin = 0.191, Tmax = 0.747 | l = −25→25 |
11320 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0358P)2 + 6.521P] where P = (Fo2 + 2Fc2)/3 |
4091 reflections | (Δ/σ)max = 0.002 |
290 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
[Cu(C11H7Br2NO5)(C3H7NO)(H2O)]·C3H7NO·H2O | V = 4662.6 (18) Å3 |
Mr = 638.76 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 46.176 (3) Å | µ = 4.42 mm−1 |
b = 5.1633 (19) Å | T = 298 K |
c = 21.793 (2) Å | 0.56 × 0.10 × 0.07 mm |
β = 116.186 (4)° |
Bruker SMART 1K CCD diffractometer | 4091 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 3197 reflections with I > 2σ(I) |
Tmin = 0.191, Tmax = 0.747 | Rint = 0.044 |
11320 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.47 e Å−3 |
4091 reflections | Δρmin = −0.34 e Å−3 |
290 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.667762 (11) | 0.45742 (9) | 0.32640 (2) | 0.03304 (14) | |
Br1 | 0.631916 (12) | 0.16100 (10) | 0.48947 (2) | 0.05071 (15) | |
Br2 | 0.550915 (11) | −0.56975 (9) | 0.29641 (3) | 0.05290 (15) | |
N1 | 0.64487 (7) | 0.2519 (6) | 0.24615 (15) | 0.0299 (7) | |
N2 | 0.70705 (8) | 0.8065 (7) | 0.51375 (15) | 0.0370 (8) | |
N3 | 0.49942 (10) | 0.0691 (9) | 0.3994 (2) | 0.0650 (12) | |
O1 | 0.68006 (6) | 0.6679 (5) | 0.26737 (13) | 0.0379 (7) | |
O2 | 0.67757 (7) | 0.6785 (6) | 0.16312 (13) | 0.0459 (7) | |
O3 | 0.59772 (7) | 0.6053 (6) | 0.12787 (15) | 0.0564 (9) | |
O4 | 0.58105 (8) | 0.3707 (7) | 0.03307 (14) | 0.0592 (9) | |
H4 | 0.5656 | 0.4695 | 0.0201 | 0.089* | |
O5 | 0.64999 (6) | 0.2798 (5) | 0.37752 (12) | 0.0377 (7) | |
O6 | 0.69090 (6) | 0.6953 (5) | 0.40330 (12) | 0.0380 (7) | |
O7 | 0.52932 (10) | 0.3581 (10) | 0.4777 (2) | 0.1011 (15) | |
O8 | 0.74314 (7) | 0.2116 (6) | 0.71684 (16) | 0.0562 (8) | |
H18 | 0.7230 | 0.2380 | 0.7012 | 0.084* | |
H19 | 0.7466 | 0.0605 | 0.7341 | 0.084* | |
O9 | 0.71561 (7) | 0.1607 (6) | 0.34796 (14) | 0.0518 (8) | |
H20 | 0.7256 | 0.1984 | 0.3244 | 0.078* | |
H21 | 0.7051 | 0.0219 | 0.3315 | 0.078* | |
C1 | 0.67179 (9) | 0.5756 (8) | 0.20757 (19) | 0.0325 (9) | |
C2 | 0.65577 (9) | 0.3065 (8) | 0.19336 (18) | 0.0338 (9) | |
H2 | 0.6732 | 0.1827 | 0.2015 | 0.041* | |
C3 | 0.63146 (9) | 0.2660 (8) | 0.11995 (18) | 0.0366 (10) | |
H3A | 0.6421 | 0.2968 | 0.0909 | 0.044* | |
H3B | 0.6247 | 0.0861 | 0.1142 | 0.044* | |
C4 | 0.60197 (10) | 0.4333 (8) | 0.0956 (2) | 0.0386 (10) | |
C5 | 0.62537 (9) | 0.0658 (8) | 0.23949 (19) | 0.0322 (9) | |
H5 | 0.6167 | −0.0235 | 0.1982 | 0.039* | |
C6 | 0.61567 (9) | −0.0170 (8) | 0.29146 (19) | 0.0314 (9) | |
C7 | 0.62860 (9) | 0.0981 (7) | 0.35723 (18) | 0.0304 (9) | |
C8 | 0.61662 (9) | 0.0012 (7) | 0.40234 (19) | 0.0323 (9) | |
C9 | 0.59465 (9) | −0.1957 (8) | 0.3859 (2) | 0.0371 (10) | |
H9 | 0.5880 | −0.2573 | 0.4177 | 0.044* | |
C10 | 0.58250 (9) | −0.3019 (7) | 0.3207 (2) | 0.0353 (9) | |
C11 | 0.59296 (9) | −0.2178 (8) | 0.2745 (2) | 0.0345 (9) | |
H11 | 0.5850 | −0.2942 | 0.2315 | 0.041* | |
C12 | 0.69048 (9) | 0.6671 (8) | 0.4600 (2) | 0.0359 (9) | |
H12 | 0.6774 | 0.5373 | 0.4638 | 0.043* | |
C13 | 0.72672 (11) | 1.0211 (9) | 0.5119 (2) | 0.0540 (12) | |
H13A | 0.7238 | 1.0466 | 0.4659 | 0.081* | |
H13B | 0.7490 | 0.9842 | 0.5410 | 0.081* | |
H13C | 0.7204 | 1.1752 | 0.5276 | 0.081* | |
C14 | 0.70679 (12) | 0.7506 (10) | 0.5795 (2) | 0.0557 (13) | |
H14A | 0.6934 | 0.6023 | 0.5748 | 0.084* | |
H14B | 0.6984 | 0.8973 | 0.5935 | 0.084* | |
H14C | 0.7284 | 0.7156 | 0.6133 | 0.084* | |
C15 | 0.52653 (13) | 0.1844 (12) | 0.4396 (3) | 0.0691 (15) | |
H15 | 0.5452 | 0.1250 | 0.4382 | 0.083* | |
C16 | 0.49831 (18) | −0.1326 (14) | 0.3523 (4) | 0.122 (3) | |
H16A | 0.5198 | −0.1692 | 0.3584 | 0.183* | |
H16B | 0.4853 | −0.0760 | 0.3062 | 0.183* | |
H16C | 0.4891 | −0.2863 | 0.3611 | 0.183* | |
C17 | 0.46963 (14) | 0.1399 (15) | 0.3995 (3) | 0.097 (2) | |
H17A | 0.4737 | 0.2536 | 0.4373 | 0.145* | |
H17B | 0.4588 | −0.0129 | 0.4038 | 0.145* | |
H17C | 0.4563 | 0.2266 | 0.3574 | 0.145* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0410 (3) | 0.0322 (3) | 0.0282 (3) | −0.0060 (2) | 0.0174 (2) | −0.0026 (2) |
Br1 | 0.0727 (3) | 0.0537 (3) | 0.0363 (2) | −0.0067 (3) | 0.0336 (2) | −0.0012 (2) |
Br2 | 0.0474 (3) | 0.0431 (3) | 0.0706 (3) | −0.0103 (2) | 0.0282 (2) | 0.0033 (2) |
N1 | 0.0345 (17) | 0.0314 (18) | 0.0297 (16) | 0.0006 (16) | 0.0197 (14) | −0.0012 (14) |
N2 | 0.0403 (19) | 0.040 (2) | 0.0302 (17) | −0.0008 (17) | 0.0149 (15) | −0.0066 (16) |
N3 | 0.060 (3) | 0.066 (3) | 0.060 (3) | −0.004 (2) | 0.018 (2) | −0.012 (2) |
O1 | 0.0504 (16) | 0.0331 (16) | 0.0333 (15) | −0.0083 (14) | 0.0213 (13) | −0.0022 (13) |
O2 | 0.0609 (19) | 0.0492 (19) | 0.0368 (16) | −0.0100 (16) | 0.0300 (15) | 0.0027 (14) |
O3 | 0.060 (2) | 0.052 (2) | 0.0504 (19) | 0.0087 (17) | 0.0179 (16) | −0.0108 (16) |
O4 | 0.056 (2) | 0.076 (3) | 0.0342 (17) | 0.0043 (18) | 0.0098 (15) | −0.0064 (17) |
O5 | 0.0487 (17) | 0.0384 (17) | 0.0305 (14) | −0.0143 (14) | 0.0214 (12) | −0.0066 (13) |
O6 | 0.0495 (17) | 0.0360 (17) | 0.0305 (15) | −0.0091 (14) | 0.0194 (13) | −0.0041 (12) |
O7 | 0.072 (3) | 0.130 (4) | 0.086 (3) | −0.023 (3) | 0.021 (2) | −0.053 (3) |
O8 | 0.0523 (19) | 0.049 (2) | 0.072 (2) | −0.0015 (16) | 0.0317 (16) | 0.0006 (17) |
O9 | 0.0545 (18) | 0.0473 (19) | 0.0528 (19) | −0.0079 (16) | 0.0228 (15) | 0.0021 (16) |
C1 | 0.031 (2) | 0.034 (2) | 0.032 (2) | 0.0023 (18) | 0.0140 (17) | −0.0036 (18) |
C2 | 0.041 (2) | 0.033 (2) | 0.034 (2) | −0.0002 (19) | 0.0231 (18) | −0.0036 (18) |
C3 | 0.045 (2) | 0.037 (2) | 0.033 (2) | −0.005 (2) | 0.0217 (18) | −0.0082 (19) |
C4 | 0.049 (3) | 0.037 (3) | 0.033 (2) | −0.008 (2) | 0.021 (2) | −0.0044 (19) |
C5 | 0.035 (2) | 0.034 (2) | 0.027 (2) | 0.0017 (19) | 0.0142 (17) | −0.0027 (18) |
C6 | 0.031 (2) | 0.029 (2) | 0.037 (2) | 0.0018 (18) | 0.0175 (17) | −0.0007 (17) |
C7 | 0.036 (2) | 0.029 (2) | 0.030 (2) | 0.0060 (19) | 0.0171 (17) | 0.0046 (17) |
C8 | 0.038 (2) | 0.028 (2) | 0.033 (2) | 0.0050 (18) | 0.0171 (17) | 0.0029 (17) |
C9 | 0.041 (2) | 0.035 (2) | 0.042 (2) | 0.005 (2) | 0.0245 (19) | 0.009 (2) |
C10 | 0.033 (2) | 0.028 (2) | 0.044 (2) | −0.0021 (18) | 0.0168 (19) | 0.0005 (19) |
C11 | 0.035 (2) | 0.033 (2) | 0.035 (2) | 0.0025 (19) | 0.0155 (18) | −0.0018 (18) |
C12 | 0.036 (2) | 0.034 (2) | 0.038 (2) | −0.0040 (19) | 0.0173 (18) | −0.0038 (19) |
C13 | 0.065 (3) | 0.044 (3) | 0.053 (3) | −0.021 (3) | 0.026 (2) | −0.013 (2) |
C14 | 0.068 (3) | 0.067 (3) | 0.038 (2) | −0.005 (3) | 0.028 (2) | −0.005 (2) |
C15 | 0.058 (3) | 0.077 (4) | 0.062 (3) | 0.003 (3) | 0.017 (3) | −0.001 (3) |
C16 | 0.110 (6) | 0.089 (5) | 0.135 (6) | 0.014 (5) | 0.024 (5) | −0.047 (5) |
C17 | 0.069 (4) | 0.134 (6) | 0.090 (5) | −0.019 (4) | 0.038 (4) | −0.025 (5) |
Cu1—O5 | 1.887 (3) | C2—H2 | 0.9800 |
Cu1—N1 | 1.916 (3) | C3—C4 | 1.498 (6) |
Cu1—O1 | 1.950 (3) | C3—H3A | 0.9700 |
Cu1—O6 | 1.969 (3) | C3—H3B | 0.9700 |
Cu1—O9 | 2.556 (3) | C5—C6 | 1.454 (5) |
Br1—C8 | 1.898 (4) | C5—H5 | 0.9300 |
Br2—C10 | 1.907 (4) | C6—C11 | 1.403 (5) |
N1—C5 | 1.281 (5) | C6—C7 | 1.417 (5) |
N1—C2 | 1.472 (5) | C7—C8 | 1.415 (5) |
N2—C12 | 1.299 (5) | C8—C9 | 1.368 (5) |
N2—C13 | 1.444 (5) | C9—C10 | 1.390 (5) |
N2—C14 | 1.467 (5) | C9—H9 | 0.9300 |
N3—C15 | 1.312 (6) | C10—C11 | 1.366 (5) |
N3—C17 | 1.424 (7) | C11—H11 | 0.9300 |
N3—C16 | 1.447 (7) | C12—H12 | 0.9300 |
O1—C1 | 1.277 (4) | C13—H13A | 0.9600 |
O2—C1 | 1.233 (4) | C13—H13B | 0.9600 |
O3—C4 | 1.202 (5) | C13—H13C | 0.9600 |
O4—C4 | 1.316 (5) | C14—H14A | 0.9600 |
O4—H4 | 0.8200 | C14—H14B | 0.9600 |
O5—C7 | 1.291 (4) | C14—H14C | 0.9600 |
O6—C12 | 1.252 (4) | C15—H15 | 0.9300 |
O7—C15 | 1.190 (7) | C16—H16A | 0.9600 |
O8—H18 | 0.8502 | C16—H16B | 0.9600 |
O8—H19 | 0.8500 | C16—H16C | 0.9600 |
O9—H20 | 0.8501 | C17—H17A | 0.9600 |
O9—H21 | 0.8500 | C17—H17B | 0.9600 |
C1—C2 | 1.540 (6) | C17—H17C | 0.9600 |
C2—C3 | 1.509 (5) | ||
O5—Cu1—N1 | 93.51 (12) | C11—C6—C7 | 120.6 (3) |
O5—Cu1—O1 | 171.55 (12) | C11—C6—C5 | 117.6 (3) |
N1—Cu1—O1 | 84.86 (12) | C7—C6—C5 | 121.8 (3) |
O5—Cu1—O6 | 90.85 (11) | O5—C7—C8 | 119.6 (3) |
N1—Cu1—O6 | 174.78 (12) | O5—C7—C6 | 124.6 (3) |
O1—Cu1—O6 | 90.42 (11) | C8—C7—C6 | 115.8 (4) |
O5—Cu1—O9 | 99.55 (11) | C9—C8—C7 | 123.6 (4) |
N1—Cu1—O9 | 85.39 (11) | C9—C8—Br1 | 119.4 (3) |
O1—Cu1—O9 | 88.60 (11) | C7—C8—Br1 | 117.0 (3) |
O6—Cu1—O9 | 96.73 (11) | C8—C9—C10 | 118.6 (4) |
C5—N1—C2 | 121.4 (3) | C8—C9—H9 | 120.7 |
C5—N1—Cu1 | 126.6 (3) | C10—C9—H9 | 120.7 |
C2—N1—Cu1 | 111.5 (2) | C11—C10—C9 | 120.9 (4) |
C12—N2—C13 | 121.9 (4) | C11—C10—Br2 | 120.1 (3) |
C12—N2—C14 | 121.1 (4) | C9—C10—Br2 | 118.9 (3) |
C13—N2—C14 | 117.0 (3) | C10—C11—C6 | 120.4 (4) |
C15—N3—C17 | 121.4 (5) | C10—C11—H11 | 119.8 |
C15—N3—C16 | 121.7 (5) | C6—C11—H11 | 119.8 |
C17—N3—C16 | 117.0 (5) | O6—C12—N2 | 124.5 (4) |
C1—O1—Cu1 | 115.0 (3) | O6—C12—H12 | 117.8 |
C4—O4—H4 | 109.5 | N2—C12—H12 | 117.8 |
C7—O5—Cu1 | 128.1 (2) | N2—C13—H13A | 109.5 |
C12—O6—Cu1 | 121.9 (3) | N2—C13—H13B | 109.5 |
H18—O8—H19 | 106.6 | H13A—C13—H13B | 109.5 |
Cu1—O9—H20 | 114.0 | N2—C13—H13C | 109.5 |
Cu1—O9—H21 | 98.3 | H13A—C13—H13C | 109.5 |
H20—O9—H21 | 107.2 | H13B—C13—H13C | 109.5 |
O2—C1—O1 | 124.7 (4) | N2—C14—H14A | 109.5 |
O2—C1—C2 | 118.8 (3) | N2—C14—H14B | 109.5 |
O1—C1—C2 | 116.2 (3) | H14A—C14—H14B | 109.5 |
N1—C2—C3 | 116.8 (3) | N2—C14—H14C | 109.5 |
N1—C2—C1 | 108.4 (3) | H14A—C14—H14C | 109.5 |
C3—C2—C1 | 113.9 (3) | H14B—C14—H14C | 109.5 |
N1—C2—H2 | 105.6 | O7—C15—N3 | 125.9 (6) |
C3—C2—H2 | 105.6 | O7—C15—H15 | 117.1 |
C1—C2—H2 | 105.6 | N3—C15—H15 | 117.1 |
C4—C3—C2 | 115.5 (3) | N3—C16—H16A | 109.5 |
C4—C3—H3A | 108.4 | N3—C16—H16B | 109.5 |
C2—C3—H3A | 108.4 | H16A—C16—H16B | 109.5 |
C4—C3—H3B | 108.4 | N3—C16—H16C | 109.5 |
C2—C3—H3B | 108.4 | H16A—C16—H16C | 109.5 |
H3A—C3—H3B | 107.5 | H16B—C16—H16C | 109.5 |
O3—C4—O4 | 123.6 (4) | N3—C17—H17A | 109.5 |
O3—C4—C3 | 125.2 (4) | N3—C17—H17B | 109.5 |
O4—C4—C3 | 111.3 (4) | H17A—C17—H17B | 109.5 |
N1—C5—C6 | 125.1 (3) | N3—C17—H17C | 109.5 |
N1—C5—H5 | 117.4 | H17A—C17—H17C | 109.5 |
C6—C5—H5 | 117.4 | H17B—C17—H17C | 109.5 |
O5—Cu1—N1—C5 | −0.2 (3) | C1—C2—C3—C4 | −65.5 (4) |
O1—Cu1—N1—C5 | −171.9 (3) | C2—C3—C4—O3 | 5.9 (6) |
O6—Cu1—N1—C5 | −146.7 (12) | C2—C3—C4—O4 | −175.0 (4) |
O9—Cu1—N1—C5 | 99.1 (3) | C2—N1—C5—C6 | 174.1 (3) |
O5—Cu1—N1—C2 | −171.9 (2) | Cu1—N1—C5—C6 | 3.2 (5) |
O1—Cu1—N1—C2 | 16.4 (2) | N1—C5—C6—C11 | 177.3 (4) |
O6—Cu1—N1—C2 | 41.6 (14) | N1—C5—C6—C7 | −3.0 (6) |
O9—Cu1—N1—C2 | −72.6 (2) | Cu1—O5—C7—C8 | −175.5 (3) |
O5—Cu1—O1—C1 | −86.2 (8) | Cu1—O5—C7—C6 | 4.6 (5) |
N1—Cu1—O1—C1 | −7.0 (3) | C11—C6—C7—O5 | 178.6 (3) |
O6—Cu1—O1—C1 | 175.2 (3) | C5—C6—C7—O5 | −1.0 (6) |
O9—Cu1—O1—C1 | 78.5 (3) | C11—C6—C7—C8 | −1.3 (5) |
N1—Cu1—O5—C7 | −3.6 (3) | C5—C6—C7—C8 | 179.1 (3) |
O1—Cu1—O5—C7 | 74.9 (9) | O5—C7—C8—C9 | −178.1 (4) |
O6—Cu1—O5—C7 | 173.5 (3) | C6—C7—C8—C9 | 1.8 (5) |
O9—Cu1—O5—C7 | −89.5 (3) | O5—C7—C8—Br1 | 2.8 (5) |
O5—Cu1—O6—C12 | 4.6 (3) | C6—C7—C8—Br1 | −177.3 (3) |
N1—Cu1—O6—C12 | 151.2 (13) | C7—C8—C9—C10 | −2.2 (6) |
O1—Cu1—O6—C12 | 176.2 (3) | Br1—C8—C9—C10 | 176.9 (3) |
O9—Cu1—O6—C12 | −95.1 (3) | C8—C9—C10—C11 | 2.1 (6) |
Cu1—O1—C1—O2 | −179.4 (3) | C8—C9—C10—Br2 | −178.2 (3) |
Cu1—O1—C1—C2 | −4.2 (4) | C9—C10—C11—C6 | −1.7 (6) |
C5—N1—C2—C3 | 36.1 (5) | Br2—C10—C11—C6 | 178.6 (3) |
Cu1—N1—C2—C3 | −151.8 (3) | C7—C6—C11—C10 | 1.3 (6) |
C5—N1—C2—C1 | 166.3 (3) | C5—C6—C11—C10 | −179.1 (4) |
Cu1—N1—C2—C1 | −21.6 (3) | Cu1—O6—C12—N2 | 175.0 (3) |
O2—C1—C2—N1 | −167.5 (3) | C13—N2—C12—O6 | 3.3 (6) |
O1—C1—C2—N1 | 17.0 (4) | C14—N2—C12—O6 | −176.1 (4) |
O2—C1—C2—C3 | −35.7 (5) | C17—N3—C15—O7 | −2.2 (10) |
O1—C1—C2—C3 | 148.8 (3) | C16—N3—C15—O7 | 176.9 (6) |
N1—C2—C3—C4 | 62.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O7i | 0.82 | 1.76 | 2.565 (5) | 169 |
O8—H18···O2ii | 0.85 | 1.93 | 2.780 (4) | 176 |
O8—H19···O8iii | 0.85 | 2.04 | 2.889 (3) | 175 |
O9—H20···O8iv | 0.85 | 2.06 | 2.904 (4) | 170 |
O9—H21···O1v | 0.85 | 2.28 | 3.116 (4) | 167 |
C3—H3A···Br1vi | 0.97 | 3.13 | 3.605 (2) | 112 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+3/2, −y+1/2, −z+1; (v) x, y−1, z; (vi) x, −y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C11H7Br2NO5)(C3H7NO)(H2O)]·C3H7NO·H2O |
Mr | 638.76 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 46.176 (3), 5.1633 (19), 21.793 (2) |
β (°) | 116.186 (4) |
V (Å3) | 4662.6 (18) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 4.42 |
Crystal size (mm) | 0.56 × 0.10 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.191, 0.747 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11320, 4091, 3197 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.087, 1.04 |
No. of reflections | 4091 |
No. of parameters | 290 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.34 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
Cu1—O5 | 1.887 (3) | Cu1—O6 | 1.969 (3) |
Cu1—N1 | 1.916 (3) | Cu1—O9 | 2.556 (3) |
Cu1—O1 | 1.950 (3) | ||
O5—Cu1—N1 | 93.51 (12) | O1—Cu1—O6 | 90.42 (11) |
O5—Cu1—O1 | 171.55 (12) | O5—Cu1—O9 | 99.55 (11) |
N1—Cu1—O1 | 84.86 (12) | N1—Cu1—O9 | 85.39 (11) |
O5—Cu1—O6 | 90.85 (11) | O1—Cu1—O9 | 88.60 (11) |
N1—Cu1—O6 | 174.78 (12) | O6—Cu1—O9 | 96.73 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O7i | 0.82 | 1.76 | 2.565 (5) | 168.5 |
O8—H18···O2ii | 0.85 | 1.93 | 2.780 (4) | 175.9 |
O8—H19···O8iii | 0.85 | 2.04 | 2.889 (3) | 175.3 |
O9—H20···O8iv | 0.85 | 2.06 | 2.904 (4) | 170.0 |
O9—H21···O1v | 0.85 | 2.28 | 3.116 (4) | 167.0 |
C3—H3A···Br1vi | 0.97 | 3.13 | 3.605 (2) | 112 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+3/2, −y+1/2, −z+1; (v) x, y−1, z; (vi) x, −y, z−1/2. |
Rencently, compounds containing dimmer water (Ghosh & Bharadwaj, 2003), water ring (Moorthy et al., 2002, Ugalde et al., 2000, Ghosh & Bharadwaj, 2004), water chain (Neogi & Bharadwaj, 2005, Cheruzel et al., 2003, Ghosh et al., 2005), metal-water chain (Ye et al., 2004), water network (Zhang et al., 2005), water-methanol intermix clusters (Raghuraman et al., 2003), and water ring chain (Feng, et al., 2007) give rise to considerable interest. Because these dimmer water, water ring, water chain, metal-water chain, water network, water ring chain and intermix clusters are potentially important form of water that is poorly understood. Water chains appear to facilitate the selective permeation (Tajkhorshid et al., 2002) of water across membranes and also to be important (Zaslavsky, & Gennis, 2000) in the control of proton fluxes in a variety of biomolecules.
The title compound, (I), is a CuII complex containing a ligand constructed from 2-(3,5-dibromo-2-hydroxy-benzylamino)-succinic acid and 3,5-dichloro-2-hydroxy-benzaldehyde. Each CuII atom is coordinated by two O atoms and one N atom from L2- and one O atom from DMF and one O atom from H2O to furnish a slightly distorted tetragonal pyramidal(Table 1). The asymmetric unit (Fig. 1) comprises one CuII complexes, one water molecule and one DMF molecule. The water molecules are linked by O—H···O hydrogen bonds (Table 2), forming a 'peral necklace' water chains. In the 'pearl necklace' water chains, the O8 water act as thread and the O9 water as pearl along 101 plan(Fig. 2). The water chains lie between layers of CuII complexes (Fig. 3), forming O—H···O hydrogen bonds to the O2 atoms of the carboxylate groups. The complex are further constructed three-dimensional supramolecular network through O—H···O hydrogen bond and C—H···Br hydrogen bond (Fig. 3).