Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047678/hy2086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047678/hy2086Isup2.hkl |
CCDC reference: 667110
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.048
- wR factor = 0.142
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of N1 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... S PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 1.99 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
L (0.100 g, 0.17 mmol) dissolved in hot ethanol (15 ml) was added to a solution of CuCl2.2H2O (0.030 g, 0.17 mmol) in hot water (10 ml). After stirring for 30 min, the mixture was filtered. Blue single crystals of the title compound were obtained after several days at room temperature.
All H atoms bound to C atoms were positioned geometrically and refined as riding, with C—H = 0.93Å (CH) and 0.97Å (CH2) and Uiso(H) = 1.2Ueq(C). The H atoms bound to N atoms and belonging to water molecule were located in a difference Fourier map and refined with Uiso(H) = 1.4Ueq(N) and Uiso(H) = 1.3Ueq(O), respectively.
The use of macrocyclic ligands for the formation of selective metal complex has received considerable attention over many years (Davis et al., 1995). The method for the synthesis of the title complex has been reported (Adam et al., 1981). However, to the best of our knowledge, the crystal structure has not been reported yet.
The molecule of the title compound is composed of two CuII atoms, four Cl- atoms, a 3,4:9,10:17,18:23,24-tetrabenzo-1,12,15,26-tetraaza- 5,8,19,22-tetraoxacyclooctacosane (L) ligand and two water molecules (Fig.1). It is a centrosymmetric molecule. Each CuII atom shows a tetragonal-pyramidal coordination geometry, formed by two Cl- atoms, two N atoms from L and one water molecule. The bond distances and angles show normal values (Table 1) (Higa et al., 2007; Jiang et al., 2007; Michalska et al., 2007; Zhou et al., 2007). There are hydrogen-bonding interactions in the crystal structure. As shown in Fig. 2 and in Table 2, there are two O—H···Cl hydrogen bonds between the water molecule and Cl- atoms, leading to a one-dimensional supramolecular structure (Barczynśki et al., 2007).
For related literature, see: Adam et al. (1981); Barczynśki et al. (2007); Davis et al. (1995); Higa et al. (2007); Jiang et al. (2007); Michalska et al. (2007); Zhou et al. (2007).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Cu2Cl4(C36H44N4O4)(H2O)2] | F(000) = 932 |
Mr = 901.66 | Dx = 1.515 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3493 reflections |
a = 13.193 (1) Å | θ = 1.8–25.1° |
b = 8.4530 (8) Å | µ = 1.40 mm−1 |
c = 17.913 (2) Å | T = 293 K |
β = 98.211 (2)° | Block, blue |
V = 1977.2 (3) Å3 | 0.45 × 0.36 × 0.24 mm |
Z = 2 |
Bruker SMART APEX CCD area-detector diffractometer | 3493 independent reflections |
Radiation source: fine-focus sealed tube | 2151 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
φ and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→14 |
Tmin = 0.55, Tmax = 0.72 | k = −10→9 |
9616 measured reflections | l = −10→21 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0678P)2] where P = (Fo2 + 2Fc2)/3 |
3493 reflections | (Δ/σ)max < 0.001 |
247 parameters | Δρmax = 0.47 e Å−3 |
2 restraints | Δρmin = −0.46 e Å−3 |
[Cu2Cl4(C36H44N4O4)(H2O)2] | V = 1977.2 (3) Å3 |
Mr = 901.66 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.193 (1) Å | µ = 1.40 mm−1 |
b = 8.4530 (8) Å | T = 293 K |
c = 17.913 (2) Å | 0.45 × 0.36 × 0.24 mm |
β = 98.211 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 3493 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2151 reflections with I > 2σ(I) |
Tmin = 0.55, Tmax = 0.72 | Rint = 0.062 |
9616 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 2 restraints |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.47 e Å−3 |
3493 reflections | Δρmin = −0.46 e Å−3 |
247 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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.44875 (4) | 0.70615 (7) | 0.52017 (3) | 0.0447 (2) | |
C1 | 0.2640 (5) | 0.4791 (7) | 0.2253 (3) | 0.0617 (15) | |
H7A | 0.2055 | 0.5058 | 0.1883 | 0.074* | |
H7B | 0.2647 | 0.3652 | 0.2320 | 0.074* | |
C2 | 0.1616 (4) | 0.5391 (6) | 0.3202 (3) | 0.0517 (14) | |
C3 | 0.0785 (5) | 0.4584 (7) | 0.2829 (4) | 0.0673 (17) | |
H4 | 0.0833 | 0.4084 | 0.2373 | 0.081* | |
C4 | −0.0119 (5) | 0.4520 (8) | 0.3135 (5) | 0.084 (2) | |
H3 | −0.0670 | 0.3950 | 0.2887 | 0.101* | |
C5 | −0.0218 (5) | 0.5281 (9) | 0.3794 (4) | 0.085 (2) | |
H2 | −0.0832 | 0.5243 | 0.3992 | 0.103* | |
C6 | 0.0609 (4) | 0.6105 (8) | 0.4161 (4) | 0.0679 (17) | |
H1 | 0.0542 | 0.6631 | 0.4607 | 0.082* | |
C7 | 0.1536 (4) | 0.6171 (6) | 0.3884 (3) | 0.0521 (14) | |
C8 | 0.2442 (4) | 0.7015 (6) | 0.4312 (3) | 0.0506 (13) | |
H16A | 0.2763 | 0.7660 | 0.3964 | 0.061* | |
H16B | 0.2207 | 0.7715 | 0.4680 | 0.061* | |
C9 | 0.2833 (4) | 0.4900 (6) | 0.5276 (3) | 0.0559 (15) | |
H17A | 0.3217 | 0.3918 | 0.5332 | 0.067* | |
H17B | 0.2117 | 0.4646 | 0.5118 | 0.067* | |
C10 | 0.2949 (4) | 0.5753 (7) | 0.6006 (3) | 0.0566 (15) | |
H18A | 0.2786 | 0.5053 | 0.6402 | 0.068* | |
H18B | 0.2484 | 0.6647 | 0.5974 | 0.068* | |
C11 | 0.5860 (4) | 0.2581 (6) | 0.3172 (3) | 0.0560 (15) | |
H15A | 0.5168 | 0.2164 | 0.3097 | 0.067* | |
H15B | 0.6327 | 0.1700 | 0.3288 | 0.067* | |
C12 | 0.6074 (5) | 0.3359 (7) | 0.2453 (3) | 0.0585 (15) | |
C13 | 0.6979 (5) | 0.3074 (8) | 0.2161 (4) | 0.0751 (19) | |
H14 | 0.7472 | 0.2411 | 0.2420 | 0.090* | |
C14 | 0.7156 (6) | 0.3762 (10) | 0.1493 (4) | 0.088 (2) | |
H13 | 0.7751 | 0.3525 | 0.1293 | 0.106* | |
C15 | 0.6462 (7) | 0.4785 (10) | 0.1127 (4) | 0.096 (3) | |
H12 | 0.6601 | 0.5272 | 0.0688 | 0.116* | |
C16 | 0.5547 (6) | 0.5120 (8) | 0.1396 (4) | 0.083 (2) | |
H11 | 0.5073 | 0.5818 | 0.1142 | 0.099* | |
C17 | 0.5361 (5) | 0.4361 (7) | 0.2071 (3) | 0.0638 (17) | |
C18 | 0.3590 (5) | 0.5285 (7) | 0.1969 (3) | 0.0703 (18) | |
H8A | 0.3551 | 0.5001 | 0.1441 | 0.084* | |
H8B | 0.3665 | 0.6424 | 0.2010 | 0.084* | |
N1 | 0.3214 (3) | 0.5906 (5) | 0.4705 (2) | 0.0453 (11) | |
N2 | 0.4025 (3) | 0.6311 (5) | 0.6184 (3) | 0.0472 (11) | |
O1 | 0.2538 (3) | 0.5538 (4) | 0.2951 (2) | 0.0561 (10) | |
O2 | 0.4457 (3) | 0.4535 (5) | 0.2392 (2) | 0.0693 (11) | |
O1W | 0.3772 (3) | 0.9524 (4) | 0.5303 (2) | 0.0613 (11) | |
Cl1 | 0.60735 (10) | 0.76791 (17) | 0.58394 (8) | 0.0568 (4) | |
Cl2 | 0.49428 (10) | 0.74432 (16) | 0.40179 (8) | 0.0546 (4) | |
H1C | 0.336 (4) | 0.521 (6) | 0.434 (3) | 0.065* | |
H2C | 0.437 (4) | 0.555 (6) | 0.631 (3) | 0.065* | |
H1A | 0.411 (4) | 1.010 (7) | 0.560 (3) | 0.082* | |
H1B | 0.361 (4) | 1.029 (6) | 0.488 (3) | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0428 (4) | 0.0478 (4) | 0.0444 (4) | −0.0036 (3) | 0.0096 (3) | −0.0014 (3) |
C1 | 0.066 (4) | 0.062 (4) | 0.053 (4) | 0.007 (3) | −0.006 (3) | −0.004 (3) |
C2 | 0.043 (3) | 0.052 (3) | 0.057 (4) | 0.001 (3) | −0.002 (3) | 0.007 (3) |
C3 | 0.064 (4) | 0.058 (4) | 0.073 (4) | −0.007 (3) | −0.013 (4) | −0.001 (3) |
C4 | 0.049 (4) | 0.086 (5) | 0.106 (6) | −0.013 (3) | −0.024 (4) | 0.025 (5) |
C5 | 0.052 (4) | 0.113 (6) | 0.090 (6) | −0.010 (4) | 0.006 (4) | 0.024 (5) |
C6 | 0.055 (4) | 0.085 (5) | 0.062 (4) | 0.008 (3) | 0.006 (3) | 0.009 (3) |
C7 | 0.043 (3) | 0.056 (3) | 0.057 (4) | 0.000 (3) | 0.005 (3) | 0.007 (3) |
C8 | 0.049 (3) | 0.052 (3) | 0.051 (3) | 0.004 (3) | 0.008 (3) | −0.003 (3) |
C9 | 0.049 (3) | 0.059 (4) | 0.058 (4) | −0.008 (3) | 0.005 (3) | 0.001 (3) |
C10 | 0.052 (3) | 0.066 (4) | 0.053 (4) | −0.011 (3) | 0.012 (3) | 0.002 (3) |
C11 | 0.057 (3) | 0.058 (4) | 0.056 (3) | −0.004 (3) | 0.018 (3) | −0.005 (3) |
C12 | 0.071 (4) | 0.061 (4) | 0.046 (3) | −0.016 (3) | 0.019 (3) | −0.009 (3) |
C13 | 0.069 (4) | 0.094 (5) | 0.069 (4) | −0.022 (4) | 0.033 (4) | −0.023 (4) |
C14 | 0.089 (6) | 0.100 (6) | 0.084 (6) | −0.027 (5) | 0.045 (5) | −0.027 (5) |
C15 | 0.116 (7) | 0.111 (7) | 0.076 (5) | −0.043 (5) | 0.062 (5) | −0.016 (5) |
C16 | 0.114 (6) | 0.075 (5) | 0.061 (4) | −0.023 (4) | 0.018 (4) | 0.006 (4) |
C17 | 0.081 (5) | 0.061 (4) | 0.053 (4) | −0.018 (3) | 0.021 (4) | −0.013 (3) |
C18 | 0.096 (5) | 0.057 (4) | 0.060 (4) | 0.001 (4) | 0.016 (4) | 0.001 (3) |
N1 | 0.040 (2) | 0.052 (3) | 0.043 (3) | −0.002 (2) | 0.005 (2) | 0.002 (2) |
N2 | 0.049 (3) | 0.047 (3) | 0.048 (3) | −0.006 (2) | 0.015 (2) | −0.005 (2) |
O1 | 0.056 (2) | 0.062 (2) | 0.049 (2) | −0.0024 (18) | 0.002 (2) | −0.0123 (19) |
O2 | 0.076 (3) | 0.087 (3) | 0.048 (2) | 0.007 (2) | 0.019 (2) | 0.006 (2) |
O1W | 0.065 (3) | 0.055 (3) | 0.068 (3) | −0.003 (2) | 0.022 (2) | −0.006 (2) |
Cl1 | 0.0484 (8) | 0.0649 (9) | 0.0568 (8) | −0.0073 (6) | 0.0069 (7) | −0.0017 (7) |
Cl2 | 0.0542 (8) | 0.0645 (9) | 0.0464 (7) | −0.0070 (6) | 0.0121 (7) | 0.0024 (7) |
Cu1—N1 | 2.035 (4) | C9—H17B | 0.9700 |
Cu1—N2 | 2.044 (4) | C10—N2 | 1.486 (6) |
Cu1—Cl1 | 2.2964 (15) | C10—H18A | 0.9700 |
Cu1—O1W | 2.303 (4) | C10—H18B | 0.9700 |
Cu1—Cl2 | 2.3078 (15) | C11—N2i | 1.477 (7) |
C1—O1 | 1.425 (6) | C11—C12 | 1.507 (7) |
C1—C18 | 1.479 (7) | C11—H15A | 0.9700 |
C1—H7A | 0.9700 | C11—H15B | 0.9700 |
C1—H7B | 0.9700 | C12—C17 | 1.373 (8) |
C2—O1 | 1.362 (6) | C12—C13 | 1.392 (7) |
C2—C3 | 1.380 (7) | C13—C14 | 1.381 (9) |
C2—C7 | 1.406 (7) | C13—H14 | 0.9300 |
C3—C4 | 1.382 (8) | C14—C15 | 1.357 (10) |
C3—H4 | 0.9300 | C14—H13 | 0.9300 |
C4—C5 | 1.368 (9) | C15—C16 | 1.391 (9) |
C4—H3 | 0.9300 | C15—H12 | 0.9300 |
C5—C6 | 1.379 (9) | C16—C17 | 1.421 (8) |
C5—H2 | 0.9300 | C16—H11 | 0.9300 |
C6—C7 | 1.385 (7) | C17—O2 | 1.403 (6) |
C6—H1 | 0.9300 | C18—O2 | 1.427 (7) |
C7—C8 | 1.504 (7) | C18—H8A | 0.9700 |
C8—N1 | 1.485 (6) | C18—H8B | 0.9700 |
C8—H16A | 0.9700 | N1—H1C | 0.93 (5) |
C8—H16B | 0.9700 | N2—C11i | 1.477 (7) |
C9—N1 | 1.474 (6) | N2—H2C | 0.80 (5) |
C9—C10 | 1.481 (7) | O1W—H1A | 0.81 (4) |
C9—H17A | 0.9700 | O1W—H1B | 1.00 (4) |
N1—Cu1—N2 | 84.17 (17) | N2—C10—H18B | 110.0 |
N1—Cu1—Cl1 | 164.46 (13) | H18A—C10—H18B | 108.3 |
N2—Cu1—Cl1 | 90.30 (13) | N2i—C11—C12 | 112.3 (4) |
N1—Cu1—O1W | 98.39 (16) | N2i—C11—H15A | 109.1 |
N2—Cu1—O1W | 92.11 (16) | C12—C11—H15A | 109.1 |
Cl1—Cu1—O1W | 96.31 (11) | N2i—C11—H15B | 109.1 |
N1—Cu1—Cl2 | 88.39 (12) | C12—C11—H15B | 109.1 |
N2—Cu1—Cl2 | 169.54 (13) | H15A—C11—H15B | 107.9 |
Cl1—Cu1—Cl2 | 94.99 (5) | C17—C12—C13 | 118.9 (6) |
O1W—Cu1—Cl2 | 96.26 (11) | C17—C12—C11 | 119.7 (5) |
O1—C1—C18 | 111.6 (5) | C13—C12—C11 | 121.4 (6) |
O1—C1—H7A | 109.3 | C14—C13—C12 | 120.9 (7) |
C18—C1—H7A | 109.3 | C14—C13—H14 | 119.6 |
O1—C1—H7B | 109.3 | C12—C13—H14 | 119.6 |
C18—C1—H7B | 109.3 | C15—C14—C13 | 120.1 (7) |
H7A—C1—H7B | 108.0 | C15—C14—H13 | 120.0 |
O1—C2—C3 | 124.9 (6) | C13—C14—H13 | 120.0 |
O1—C2—C7 | 115.1 (5) | C14—C15—C16 | 121.4 (7) |
C3—C2—C7 | 120.0 (5) | C14—C15—H12 | 119.3 |
C2—C3—C4 | 119.9 (6) | C16—C15—H12 | 119.3 |
C2—C3—H4 | 120.0 | C15—C16—C17 | 117.8 (7) |
C4—C3—H4 | 120.0 | C15—C16—H11 | 121.1 |
C5—C4—C3 | 121.2 (7) | C17—C16—H11 | 121.1 |
C5—C4—H3 | 119.4 | C12—C17—O2 | 115.0 (5) |
C3—C4—H3 | 119.4 | C12—C17—C16 | 120.9 (6) |
C4—C5—C6 | 118.8 (6) | O2—C17—C16 | 124.2 (6) |
C4—C5—H2 | 120.6 | O2—C18—C1 | 110.3 (5) |
C6—C5—H2 | 120.6 | O2—C18—H8A | 109.6 |
C5—C6—C7 | 122.0 (6) | C1—C18—H8A | 109.6 |
C5—C6—H1 | 119.0 | O2—C18—H8B | 109.6 |
C7—C6—H1 | 119.0 | C1—C18—H8B | 109.6 |
C6—C7—C2 | 118.1 (5) | H8A—C18—H8B | 108.1 |
C6—C7—C8 | 121.0 (5) | C9—N1—C8 | 114.5 (4) |
C2—C7—C8 | 120.8 (5) | C9—N1—Cu1 | 108.4 (3) |
N1—C8—C7 | 112.5 (4) | C8—N1—Cu1 | 111.8 (3) |
N1—C8—H16A | 109.1 | C9—N1—H1C | 105 (3) |
C7—C8—H16A | 109.1 | C8—N1—H1C | 105 (3) |
N1—C8—H16B | 109.1 | Cu1—N1—H1C | 112 (3) |
C7—C8—H16B | 109.1 | C11i—N2—C10 | 110.9 (4) |
H16A—C8—H16B | 107.8 | C11i—N2—Cu1 | 117.8 (3) |
N1—C9—C10 | 109.2 (4) | C10—N2—Cu1 | 107.9 (3) |
N1—C9—H17A | 109.8 | C11i—N2—H2C | 107 (4) |
C10—C9—H17A | 109.8 | C10—N2—H2C | 107 (4) |
N1—C9—H17B | 109.8 | Cu1—N2—H2C | 106 (4) |
C10—C9—H17B | 109.8 | C2—O1—C1 | 116.7 (4) |
H17A—C9—H17B | 108.3 | C17—O2—C18 | 119.5 (5) |
C9—C10—N2 | 108.6 (4) | Cu1—O1W—H1A | 113 (5) |
C9—C10—H18A | 110.0 | Cu1—O1W—H1B | 125 (3) |
N2—C10—H18A | 110.0 | H1A—O1W—H1B | 99 (5) |
C9—C10—H18B | 110.0 | ||
O1—C2—C3—C4 | −179.6 (5) | C10—C9—N1—C8 | −86.8 (5) |
C7—C2—C3—C4 | −1.2 (8) | C10—C9—N1—Cu1 | 38.8 (5) |
C2—C3—C4—C5 | 1.8 (10) | C7—C8—N1—C9 | −61.3 (6) |
C3—C4—C5—C6 | −0.9 (11) | C7—C8—N1—Cu1 | 175.0 (3) |
C4—C5—C6—C7 | −0.6 (10) | N2—Cu1—N1—C9 | −13.3 (3) |
C5—C6—C7—C2 | 1.1 (9) | Cl1—Cu1—N1—C9 | 56.3 (6) |
C5—C6—C7—C8 | −177.2 (6) | O1W—Cu1—N1—C9 | −104.6 (3) |
O1—C2—C7—C6 | 178.3 (5) | Cl2—Cu1—N1—C9 | 159.3 (3) |
C3—C2—C7—C6 | −0.3 (8) | N2—Cu1—N1—C8 | 113.8 (3) |
O1—C2—C7—C8 | −3.3 (7) | Cl1—Cu1—N1—C8 | −176.5 (3) |
C3—C2—C7—C8 | 178.1 (5) | O1W—Cu1—N1—C8 | 22.5 (3) |
C6—C7—C8—N1 | 103.8 (6) | Cl2—Cu1—N1—C8 | −73.6 (3) |
C2—C7—C8—N1 | −74.6 (6) | C9—C10—N2—C11i | 169.4 (4) |
N1—C9—C10—N2 | −52.1 (6) | C9—C10—N2—Cu1 | 39.0 (5) |
N2i—C11—C12—C17 | −75.4 (7) | N1—Cu1—N2—C11i | −140.6 (4) |
N2i—C11—C12—C13 | 105.2 (6) | Cl1—Cu1—N2—C11i | 54.0 (4) |
C17—C12—C13—C14 | −1.0 (9) | O1W—Cu1—N2—C11i | −42.3 (4) |
C11—C12—C13—C14 | 178.4 (6) | Cl2—Cu1—N2—C11i | 174.5 (5) |
C12—C13—C14—C15 | 2.8 (10) | N1—Cu1—N2—C10 | −14.1 (3) |
C13—C14—C15—C16 | −2.4 (11) | Cl1—Cu1—N2—C10 | −179.5 (3) |
C14—C15—C16—C17 | 0.3 (10) | O1W—Cu1—N2—C10 | 84.2 (3) |
C13—C12—C17—O2 | 177.9 (5) | Cl2—Cu1—N2—C10 | −59.0 (9) |
C11—C12—C17—O2 | −1.5 (8) | C3—C2—O1—C1 | −0.2 (7) |
C13—C12—C17—C16 | −1.1 (9) | C7—C2—O1—C1 | −178.7 (5) |
C11—C12—C17—C16 | 179.5 (5) | C18—C1—O1—C2 | 169.0 (5) |
C15—C16—C17—C12 | 1.5 (9) | C12—C17—O2—C18 | −167.5 (5) |
C15—C16—C17—O2 | −177.4 (6) | C16—C17—O2—C18 | 11.4 (8) |
O1—C1—C18—O2 | 74.8 (6) | C1—C18—O2—C17 | 157.1 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1B···Cl1ii | 1.00 (4) | 2.22 (5) | 3.152 (4) | 155 (5) |
O1W—H1A···Cl2ii | 0.81 (4) | 2.47 (5) | 3.215 (4) | 154 (6) |
Symmetry code: (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu2Cl4(C36H44N4O4)(H2O)2] |
Mr | 901.66 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 13.193 (1), 8.4530 (8), 17.913 (2) |
β (°) | 98.211 (2) |
V (Å3) | 1977.2 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.45 × 0.36 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.55, 0.72 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9616, 3493, 2151 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.142, 1.01 |
No. of reflections | 3493 |
No. of parameters | 247 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.46 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Siemens, 1990).
Cu1—N1 | 2.035 (4) | Cu1—O1W | 2.303 (4) |
Cu1—N2 | 2.044 (4) | Cu1—Cl2 | 2.3078 (15) |
Cu1—Cl1 | 2.2964 (15) | ||
N1—Cu1—N2 | 84.17 (17) | Cl1—Cu1—O1W | 96.31 (11) |
N1—Cu1—Cl1 | 164.46 (13) | N1—Cu1—Cl2 | 88.39 (12) |
N2—Cu1—Cl1 | 90.30 (13) | N2—Cu1—Cl2 | 169.54 (13) |
N1—Cu1—O1W | 98.39 (16) | Cl1—Cu1—Cl2 | 94.99 (5) |
N2—Cu1—O1W | 92.11 (16) | O1W—Cu1—Cl2 | 96.26 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1B···Cl1i | 1.00 (4) | 2.22 (5) | 3.152 (4) | 155 (5) |
O1W—H1A···Cl2i | 0.81 (4) | 2.47 (5) | 3.215 (4) | 154 (6) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
The use of macrocyclic ligands for the formation of selective metal complex has received considerable attention over many years (Davis et al., 1995). The method for the synthesis of the title complex has been reported (Adam et al., 1981). However, to the best of our knowledge, the crystal structure has not been reported yet.
The molecule of the title compound is composed of two CuII atoms, four Cl- atoms, a 3,4:9,10:17,18:23,24-tetrabenzo-1,12,15,26-tetraaza- 5,8,19,22-tetraoxacyclooctacosane (L) ligand and two water molecules (Fig.1). It is a centrosymmetric molecule. Each CuII atom shows a tetragonal-pyramidal coordination geometry, formed by two Cl- atoms, two N atoms from L and one water molecule. The bond distances and angles show normal values (Table 1) (Higa et al., 2007; Jiang et al., 2007; Michalska et al., 2007; Zhou et al., 2007). There are hydrogen-bonding interactions in the crystal structure. As shown in Fig. 2 and in Table 2, there are two O—H···Cl hydrogen bonds between the water molecule and Cl- atoms, leading to a one-dimensional supramolecular structure (Barczynśki et al., 2007).