Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The crystal structure of the title complex, trans-di­chloridotetra­kis­[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN4)pro­pan-1-one]copper(II) hexa­hydrate, [CuCl2(C11H11N3O)4]·6H2O, is isomorphous with that of the corresponding nickel and cobalt compounds. The complex has crystallographic inversion symmetry with the CuII atom on an inversion centre. Each CuII atom is six-coordinated by one N atom from each of the four 1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one ligands in the equatorial plane and by two chloride ligands in axial positions. The structure includes a centrosymmetric irregular up–up–down–down (uudd) water tetra­mer cluster and O—H...Cl hydrogen bonds. Inter­molecular C—H...Cl hydrogen bonds exist between adjacent mol­ecules, resulting in a three-dimensional supramolecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112045362/sk3456sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112045362/sk3456Isup2.hkl
Contains datablock I

CCDC reference: 821945

Comment top

Noncovalent interactions have received much interest in crystal engineering of supramolecular architecture. A convenient and efficient approach to crystal engineering is the synthesis of reliable synthons that can control the dimensionality of the molecular architecture. Classical hydrogen-bonding interactions have played an important role in crystal engineering and have been investigated in much detail (Moulton & Zaworotko, 2001; Desiraju, 2002; Steiner, 2002; Beatty, 2003; Aakeröy & Seddon, 1993; Aakeröy & Beatty, 2001; Janiak, 2000; Braga & Grepioni, 2000), while the studies of other weak interactions, such as halogen-bond contacts, have received attention only in more recent years (Fourmigue & Batail, 2004; Metrangolo et al., 2005; Metrangolo et al., 2006; Politzer et al., 2007). Neutral organic ligands containing rigid or flexible triazole-like spacers, such as 1,4-bis(triazol-1-ylmethyl)benzene, have been used to generate a rich variety of metal–organic architectures with different metal ions by various reaction procedures (Ding et al., 2009). In our recent research, the 1-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-1-one (L) ligand, with two methylene Csp3 atoms, is highly flexible and can assume a variable dihedral angle. These ligands can produce architectures quite different from those obtained from triazole-based ligands. For the L ligand, a variety of nickel and cobalt compounds have been reported (Jian et al., 2003, 2004; Guo, 2010), while for CuII fewer compounds have been reported.

As a continuation of this work, we report here the title mononuclear copper(II) complex [CuCl2L4].6H2O, (I), which is located on an inversion centre (Fig. 1). The CuII ion is six-coordinated by four N atoms [N1, N4, N1i and N4i; symmetry code: (i) -x, -y + 1, -z] from four L ligands and by two chloride atoms (Cl1 and Cl1i). The structure is completed by three independent solvent water molecules (O3, O4 and O5). The axial Cu—Cl distances [2.7738 (5) Å] are much longer than the Cu—N distances [2.0364 (15) and 2.0206 (15) Å], indicative of a distorted octahedral environment with [Which?] axis elongated. The triazole and phenyl rings of L are not coplanar: the corresponding dihedral angles formed by the least-squares planes of the phenyl and triazole rings are 69.27 (11) and 52.74 (11)°, respectively.

All water H atoms could be located in the Fourier difference map and all are involved in hydrogen bonds; the geometric parameters of the hydrogen bonding are collected in Table 2. It is interesting that a cyclic water tetramer is located in between and parallel to two Cu atoms, formed by hydrogen bonding between atoms O3, Cl1iii, O5 and O4 and their symmetry-related counterparts [Revised text OK?] [O5—H5B···O3 = 2.837 (3) Å and O4—H4A···Cl1iii = 3.1469 (18) Å; symmetry code: x + 1, y, z]. The coordination environment of the water tetramers is shown in Fig. 2. Each water molecule in the cluster is involved in the formation of three hydrogen bonds, two from a water–water interaction and one from a water–host interaction. Within the cluster, the four water molecules are fully coplanar and each water monomer acts as both a single hydrogen-bond donor and acceptor. Such an arrangement results in the formation of an irregular up–up–down–down (uudd) water tetramer that was also reported by Long et al. (2004). The hydrogen-bond distances and angles within the water tetramer are as follows: O4···O5 = 2.808 (3) Å, O5···O4iv = 2.826 (3) Å, O4—H4B···O5 = 147° and O5—H5A···O4iv = 131°. The average hydrogen-bond distance within the water tetramer is 2.816 Å, significantly longer than the value of 2.78 Å found in the udud water tetramer of (D2O)4 in the gas phase (Cruzan et al., 1996) and the value of 2.743 Å calculated in the discrete udud water tetramer (Xantheas, 1994, 1995).

There are two chloride anions in the asymmetric unit of (I), each with the same supramolecular contacts and function. Atom Cl1 links the tetramers into a one-dimensional chain (Fig. 3). Each Cl atom forms two hydrogen bonds with an average (O)H···Cl1 distance of 2.325 Å. As shown in Fig. 4, the O atoms of the solvent water molecules, the Cl atoms and the N atoms from the ligands generate the intermolecular hydrogen bonding and form a novel two-dimensional layer in the ab plane. Intermolecular C9—H9···Cl1v (see Table 2 for details) hydrogen bonds extend these two-dimensional layers to generate a three-dimensional supramolecular network in the bc plane, as shown in Fig. 5.

In summary, weak C—H···Cl hydrogen-bond interactions are quite important for the assembly of three-dimensional supramolecular architectures. Subtle changes inthese weak interactions, such as the formation of water clusters, may be helpful for a deeper understanding of similar weak interactions as important driving forces in biological systems.

Related literature top

For related literature, see: Aakeröy & Beatty (2001); Aakeröy & Seddon (1993); Beatty (2003); Braga & Grepioni (2000); Cruzan et al. (1996); Desiraju (2002); Ding et al. (2009); Fourmigue & Batail (2004); Guo (2010); Janiak (2000); Jian et al. (2003, 2004); Long et al. (2004); Metrangolo et al. (2005, 2006); Moulton & Zaworotko (2001); Politzer et al. (2007); Steiner (2002); Xantheas (1994, 1995).

Experimental top

NH4SCN (7.6 mg, 0.1 mmol) was added to an acetonitrile solution of the ligand L (25.6 mg, 0.1 mmol) with stirring. The resulting mixture was then added to a solution of CuCl2.2H2O (17.0 mg, 0.1 mmol) in acetonitrile–H2O (10 ml, 1:1 v/v) with vigorous stirring for ca 30 min. The reaction solution was filtered and left to stand at room temperature. Green crystals of (I) suitable for X-ray diffraction were obtained by evaporation of the filtrate (yield 40%, based on CuII). Analysis, calculated for C44H44Cl2CuN12O4.6H2O: C 50.45, H 5.39, N 16.05%; found: C 50.31, H 5.32, N 16.19%.

Refinement top

Although all H atoms were visible in difference maps, they were finally placed in calculated positions, with C—H and O—H distances of 0.93–0.97 and 0.85 Å, respectively, and included in the final refinement in a riding-model approximation, with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms, or Uiso(H) = 1.5Ueq(C) for water H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2 (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the local coordination of the CuII cation in (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) -x, -y + 1, -z.]
[Figure 2] Fig. 2. The coordination environment of the water tetramers of complex (I). Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) -x + 1, -y, -z; (ii) -x, -y, -z; (iii) x + 1, y, z.]
[Figure 3] Fig. 3. The one-dimensional chain structure of complex (I). Dashed lines indicate hydrogen bonds.
[Figure 4] Fig. 4. The two-dimensional square-grid structure of complex (I). Dashed lines indicate hydrogen bonds.
[Figure 5] Fig. 5. The one-dimensional channel in the three-dimensional supramolecular structure of (I), in the bc plane. Dashed lines indicate hydrogen bonds.
trans-dichloridotetrakis[1-phenyl-3-(1H-1,2,4-triazol-1-yl- κN4)propan-1-one]copper(II) hexahydrate top
Crystal data top
[CuCl2(C11H11N3O)4]·6H2OF(000) = 1094
Mr = 1047.45Dx = 1.393 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4452 reflections
a = 7.9853 (6) Åθ = 2.4–25.4°
b = 10.8365 (7) ŵ = 0.61 mm1
c = 28.974 (2) ÅT = 293 K
β = 95.123 (1)°Block, green
V = 2497.2 (3) Å30.32 × 0.28 × 0.22 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5891 independent reflections
Radiation source: fine-focus sealed tube4473 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ϕ and ω scansθmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1010
Tmin = 0.828, Tmax = 0.877k = 1412
16593 measured reflectionsl = 3835
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0421P)2 + 0.6416P]
where P = (Fo2 + 2Fc2)/3
5891 reflections(Δ/σ)max < 0.001
313 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[CuCl2(C11H11N3O)4]·6H2OV = 2497.2 (3) Å3
Mr = 1047.45Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.9853 (6) ŵ = 0.61 mm1
b = 10.8365 (7) ÅT = 293 K
c = 28.974 (2) Å0.32 × 0.28 × 0.22 mm
β = 95.123 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5891 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
4473 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 0.877Rint = 0.023
16593 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.05Δρmax = 0.36 e Å3
5891 reflectionsΔρmin = 0.29 e Å3
313 parameters
Special details top

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) top
xyzUiso*/Ueq
Cu10.00000.50000.00000.03106 (9)
Cl10.18258 (6)0.34110 (4)0.051372 (15)0.04099 (12)
O10.2697 (2)0.65408 (13)0.17904 (6)0.0686 (5)
O20.6076 (2)0.15005 (13)0.19332 (5)0.0613 (4)
O30.0150 (2)0.09050 (14)0.07526 (6)0.0724 (5)
H3A0.03290.02060.07200.087*
H3B0.04670.15170.06650.087*
O40.5432 (3)0.17508 (19)0.00309 (7)0.0943 (7)
H4A0.61110.22760.00990.113*
H4B0.51750.11300.01300.113*
O50.3414 (3)0.0316 (2)0.05056 (8)0.1026 (7)
H5A0.32010.01540.02770.123*
H5B0.25870.07090.05920.123*
N10.07581 (18)0.64617 (12)0.03713 (5)0.0320 (3)
N20.1027 (2)0.84014 (14)0.06113 (6)0.0463 (4)
N30.21651 (18)0.76593 (13)0.07922 (5)0.0344 (3)
N40.20256 (17)0.47475 (12)0.04594 (5)0.0322 (3)
N50.38467 (18)0.39148 (13)0.09646 (5)0.0340 (3)
N60.4476 (2)0.50480 (14)0.08814 (6)0.0455 (4)
C10.1986 (2)0.65168 (16)0.06465 (6)0.0341 (4)
H10.26320.58480.07260.041*
C20.0212 (3)0.76395 (17)0.03612 (6)0.0425 (4)
H20.06650.78880.01920.051*
C30.3371 (2)0.81892 (19)0.10882 (6)0.0452 (5)
H3A'0.42190.75770.11420.054*
H3B'0.39310.88860.09310.054*
C40.2517 (2)0.86114 (17)0.15501 (6)0.0401 (4)
H4A'0.14320.89660.15010.048*
H4B'0.31920.92530.16760.048*
C50.2267 (2)0.75801 (17)0.18972 (6)0.0406 (4)
C60.1487 (2)0.78626 (17)0.23705 (6)0.0385 (4)
C70.0823 (3)0.90101 (19)0.24902 (7)0.0482 (5)
H70.08800.96460.22740.058*
C80.0069 (3)0.9209 (2)0.29354 (7)0.0596 (6)
H80.03830.99790.30160.072*
C90.0011 (3)0.8283 (3)0.32547 (7)0.0624 (6)
H90.05190.84220.35520.075*
C100.0654 (3)0.7147 (2)0.31406 (8)0.0635 (6)
H100.06020.65190.33600.076*
C110.1397 (3)0.6935 (2)0.27019 (7)0.0536 (5)
H110.18440.61610.26260.064*
C120.3340 (2)0.55063 (18)0.05777 (6)0.0424 (4)
H120.34270.62920.04530.051*
C130.2404 (2)0.37564 (17)0.07120 (6)0.0371 (4)
H130.17480.30470.07120.045*
C140.4767 (2)0.30298 (17)0.12726 (6)0.0395 (4)
H14A0.58400.28500.11550.047*
H14B0.41340.22660.12740.047*
C150.5066 (2)0.35133 (16)0.17636 (6)0.0380 (4)
H15A0.57930.42310.17680.046*
H15B0.40040.37630.18730.046*
C160.5870 (2)0.25317 (17)0.20801 (6)0.0383 (4)
C170.6397 (2)0.28372 (17)0.25732 (6)0.0381 (4)
C180.7150 (3)0.1921 (2)0.28553 (7)0.0530 (5)
H180.72900.11350.27350.064*
C190.7694 (3)0.2165 (3)0.33131 (8)0.0642 (6)
H190.82090.15490.34990.077*
C200.7471 (3)0.3318 (3)0.34914 (7)0.0625 (6)
H200.78390.34840.37990.075*
C210.6713 (3)0.4224 (2)0.32215 (7)0.0596 (6)
H210.65570.50030.33460.072*
C220.6172 (3)0.39892 (19)0.27614 (7)0.0477 (5)
H220.56550.46110.25790.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03373 (16)0.03098 (16)0.02706 (15)0.00256 (12)0.00507 (11)0.00742 (11)
Cl10.0458 (3)0.0407 (2)0.0371 (2)0.00502 (19)0.00724 (19)0.00097 (18)
O10.0981 (13)0.0392 (9)0.0639 (10)0.0081 (8)0.0183 (9)0.0068 (7)
O20.0895 (12)0.0385 (8)0.0522 (9)0.0086 (8)0.0145 (8)0.0008 (7)
O30.0804 (12)0.0396 (9)0.0962 (13)0.0028 (8)0.0024 (10)0.0011 (8)
O40.1078 (16)0.0795 (13)0.0904 (14)0.0414 (12)0.0204 (12)0.0056 (10)
O50.0930 (16)0.1017 (16)0.1142 (18)0.0024 (12)0.0147 (13)0.0027 (13)
N10.0364 (8)0.0310 (7)0.0282 (7)0.0015 (6)0.0018 (6)0.0060 (6)
N20.0634 (11)0.0322 (8)0.0446 (9)0.0036 (7)0.0125 (8)0.0075 (7)
N30.0374 (8)0.0367 (8)0.0288 (7)0.0023 (6)0.0014 (6)0.0054 (6)
N40.0333 (8)0.0321 (8)0.0301 (7)0.0028 (6)0.0026 (6)0.0016 (6)
N50.0348 (8)0.0349 (8)0.0313 (7)0.0027 (6)0.0031 (6)0.0035 (6)
N60.0415 (9)0.0406 (9)0.0513 (9)0.0109 (7)0.0125 (7)0.0092 (7)
C10.0351 (9)0.0320 (9)0.0346 (9)0.0019 (7)0.0003 (7)0.0045 (7)
C20.0526 (12)0.0358 (10)0.0410 (10)0.0086 (8)0.0144 (9)0.0081 (8)
C30.0415 (11)0.0567 (12)0.0368 (10)0.0155 (9)0.0006 (8)0.0094 (9)
C40.0468 (11)0.0397 (10)0.0339 (9)0.0076 (8)0.0040 (8)0.0078 (8)
C50.0409 (10)0.0395 (10)0.0414 (10)0.0041 (8)0.0025 (8)0.0069 (8)
C60.0389 (10)0.0411 (10)0.0360 (9)0.0041 (8)0.0059 (8)0.0024 (8)
C70.0565 (13)0.0494 (12)0.0379 (10)0.0070 (10)0.0008 (9)0.0019 (9)
C80.0597 (14)0.0709 (16)0.0470 (12)0.0109 (12)0.0020 (10)0.0140 (11)
C90.0534 (13)0.098 (2)0.0346 (11)0.0095 (13)0.0035 (9)0.0055 (12)
C100.0773 (17)0.0725 (16)0.0406 (12)0.0171 (13)0.0053 (11)0.0105 (11)
C110.0666 (14)0.0477 (12)0.0467 (12)0.0037 (10)0.0067 (10)0.0045 (9)
C120.0454 (11)0.0352 (10)0.0441 (10)0.0090 (8)0.0096 (9)0.0068 (8)
C130.0366 (10)0.0367 (9)0.0368 (9)0.0061 (7)0.0038 (7)0.0007 (7)
C140.0421 (10)0.0395 (10)0.0356 (9)0.0049 (8)0.0033 (8)0.0046 (8)
C150.0392 (10)0.0377 (10)0.0358 (9)0.0001 (8)0.0028 (7)0.0038 (7)
C160.0383 (10)0.0360 (10)0.0396 (10)0.0027 (8)0.0024 (8)0.0044 (8)
C170.0332 (9)0.0443 (10)0.0363 (9)0.0023 (8)0.0010 (7)0.0077 (8)
C180.0589 (14)0.0539 (13)0.0452 (11)0.0064 (10)0.0011 (10)0.0108 (9)
C190.0633 (15)0.0847 (18)0.0428 (12)0.0104 (13)0.0059 (10)0.0190 (12)
C200.0528 (13)0.099 (2)0.0347 (11)0.0012 (13)0.0029 (9)0.0019 (12)
C210.0611 (14)0.0706 (16)0.0461 (12)0.0019 (12)0.0008 (10)0.0115 (11)
C220.0503 (12)0.0498 (12)0.0418 (11)0.0040 (9)0.0031 (9)0.0022 (9)
Geometric parameters (Å, º) top
Cu1—N42.0196 (13)C4—H4B'0.9700
Cu1—N4i2.0196 (13)C5—C61.486 (2)
Cu1—N12.0370 (13)C6—C71.384 (3)
Cu1—N1i2.0370 (13)C6—C111.388 (3)
Cu1—Cl12.7738 (5)C7—C81.391 (3)
Cu1—Cl1i2.7738 (5)C7—H70.9300
O1—C51.210 (2)C8—C91.363 (3)
O2—C161.212 (2)C8—H80.9300
O3—H3A0.8504C9—C101.369 (3)
O3—H3B0.8506C9—H90.9300
O4—H4A0.8500C10—C111.373 (3)
O4—H4B0.8544C10—H100.9300
O5—H5A0.8407C11—H110.9300
O5—H5B0.8418C12—H120.9300
N1—C11.319 (2)C13—H130.9300
N1—C21.350 (2)C14—C151.515 (2)
N2—C21.309 (2)C14—H14A0.9700
N2—N31.354 (2)C14—H14B0.9700
N3—C11.320 (2)C15—C161.510 (2)
N3—C31.463 (2)C15—H15A0.9700
N4—C131.319 (2)C15—H15B0.9700
N4—C121.353 (2)C16—C171.490 (2)
N5—C131.320 (2)C17—C221.380 (3)
N5—N61.3566 (19)C17—C181.389 (3)
N5—C141.462 (2)C18—C191.384 (3)
N6—C121.304 (2)C18—H180.9300
C1—H10.9300C19—C201.370 (3)
C2—H20.9300C19—H190.9300
C3—C41.517 (2)C20—C211.363 (3)
C3—H3A'0.9700C20—H200.9300
C3—H3B'0.9700C21—C221.388 (3)
C4—C51.505 (3)C21—H210.9300
C4—H4A'0.9700C22—H220.9300
N4—Cu1—N4i180C9—C8—H8119.8
N4—Cu1—N190.89 (5)C7—C8—H8119.8
N4i—Cu1—N189.11 (5)C8—C9—C10120.3 (2)
N4—Cu1—N1i89.11 (5)C8—C9—H9119.8
N4i—Cu1—N1i90.89 (5)C10—C9—H9119.8
N1—Cu1—N1i180C9—C10—C11120.0 (2)
H3A—O3—H3B114.8C9—C10—H10120.0
H4A—O4—H4B117.3C11—C10—H10120.0
H5A—O5—H5B115.5C10—C11—C6120.7 (2)
C1—N1—C2103.27 (14)C10—C11—H11119.6
C1—N1—Cu1128.79 (11)C6—C11—H11119.6
C2—N1—Cu1127.71 (12)N6—C12—N4114.62 (16)
C2—N2—N3102.93 (14)N6—C12—H12122.7
C1—N3—N2109.75 (14)N4—C12—H12122.7
C1—N3—C3130.63 (16)N4—C13—N5110.30 (15)
N2—N3—C3119.59 (15)N4—C13—H13124.8
C13—N4—C12102.72 (14)N5—C13—H13124.8
C13—N4—Cu1127.31 (12)N5—C14—C15112.01 (15)
C12—N4—Cu1129.95 (12)N5—C14—H14A109.2
C13—N5—N6109.76 (14)C15—C14—H14A109.2
C13—N5—C14128.26 (15)N5—C14—H14B109.2
N6—N5—C14121.88 (14)C15—C14—H14B109.2
C12—N6—N5102.60 (14)H14A—C14—H14B107.9
N1—C1—N3110.06 (15)C16—C15—C14110.45 (15)
N1—C1—H1125.0C16—C15—H15A109.6
N3—C1—H1125.0C14—C15—H15A109.6
N2—C2—N1113.98 (17)C16—C15—H15B109.6
N2—C2—H2123.0C14—C15—H15B109.6
N1—C2—H2123.0H15A—C15—H15B108.1
N3—C3—C4111.58 (15)O2—C16—C17120.38 (16)
N3—C3—H3A'109.3O2—C16—C15120.02 (17)
C4—C3—H3A'109.3C17—C16—C15119.61 (16)
N3—C3—H3B'109.3C22—C17—C18118.62 (18)
C4—C3—H3B'109.3C22—C17—C16122.96 (16)
H3A'—C3—H3B'108.0C18—C17—C16118.41 (18)
C5—C4—C3112.82 (16)C19—C18—C17120.6 (2)
C5—C4—H4A'109.0C19—C18—H18119.7
C3—C4—H4A'109.0C17—C18—H18119.7
C5—C4—H4B'109.0C20—C19—C18119.7 (2)
C3—C4—H4B'109.0C20—C19—H19120.1
H4A'—C4—H4B'107.8C18—C19—H19120.1
O1—C5—C6120.91 (18)C21—C20—C19120.5 (2)
O1—C5—C4120.19 (17)C21—C20—H20119.8
C6—C5—C4118.90 (16)C19—C20—H20119.8
C7—C6—C11118.84 (18)C20—C21—C22120.2 (2)
C7—C6—C5122.40 (17)C20—C21—H21119.9
C11—C6—C5118.75 (18)C22—C21—H21119.9
C6—C7—C8119.8 (2)C17—C22—C21120.35 (19)
C6—C7—H7120.1C17—C22—H22119.8
C8—C7—H7120.1C21—C22—H22119.8
C9—C8—C7120.4 (2)
N4—Cu1—N1—C1104.33 (15)C6—C7—C8—C90.3 (3)
N4i—Cu1—N1—C175.67 (15)C7—C8—C9—C100.2 (4)
N4—Cu1—N1—C282.13 (15)C8—C9—C10—C110.4 (4)
N4i—Cu1—N1—C297.87 (15)C9—C10—C11—C60.2 (4)
C2—N2—N3—C10.0 (2)C7—C6—C11—C100.3 (3)
C2—N2—N3—C3178.24 (16)C5—C6—C11—C10178.6 (2)
N1—Cu1—N4—C13119.76 (15)N5—N6—C12—N40.1 (2)
N1i—Cu1—N4—C1360.24 (15)C13—N4—C12—N60.0 (2)
N1—Cu1—N4—C1262.34 (17)Cu1—N4—C12—N6178.30 (13)
N1i—Cu1—N4—C12117.66 (17)C12—N4—C13—N50.1 (2)
C13—N5—N6—C120.1 (2)Cu1—N4—C13—N5178.45 (11)
C14—N5—N6—C12176.73 (17)N6—N5—C13—N40.1 (2)
C2—N1—C1—N30.03 (19)C14—N5—C13—N4176.48 (16)
Cu1—N1—C1—N3174.73 (11)C13—N5—C14—C15122.42 (19)
N2—N3—C1—N10.0 (2)N6—N5—C14—C1561.6 (2)
C3—N3—C1—N1177.98 (16)N5—C14—C15—C16174.65 (15)
N3—N2—C2—N10.0 (2)C14—C15—C16—O25.0 (3)
C1—N1—C2—N20.0 (2)C14—C15—C16—C17175.35 (16)
Cu1—N1—C2—N2174.81 (13)O2—C16—C17—C22179.0 (2)
C1—N3—C3—C4112.7 (2)C15—C16—C17—C220.6 (3)
N2—N3—C3—C469.5 (2)O2—C16—C17—C181.0 (3)
N3—C3—C4—C583.5 (2)C15—C16—C17—C18179.31 (18)
C3—C4—C5—O11.7 (3)C22—C17—C18—C191.3 (3)
C3—C4—C5—C6178.31 (16)C16—C17—C18—C19178.6 (2)
O1—C5—C6—C7173.1 (2)C17—C18—C19—C200.7 (4)
C4—C5—C6—C76.9 (3)C18—C19—C20—C210.2 (4)
O1—C5—C6—C115.7 (3)C19—C20—C21—C220.6 (4)
C4—C5—C6—C11174.27 (18)C18—C17—C22—C210.9 (3)
C11—C6—C7—C80.5 (3)C16—C17—C22—C21179.01 (19)
C5—C6—C7—C8178.3 (2)C20—C21—C22—C170.0 (3)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N2ii0.852.052.888 (2)169
O3—H3B···Cl10.852.343.1853 (17)170
O4—H4A···Cl1iii0.852.313.1469 (18)170
O4—H4B···O50.852.052.807 (3)147
O5—H5A···O4iv0.842.202.825 (3)131
O5—H5B···O30.842.052.837 (3)155
C9—H9···Cl1v0.932.813.732 (2)169
Symmetry codes: (ii) x, y1, z; (iii) x+1, y, z; (iv) x+1, y, z; (v) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[CuCl2(C11H11N3O)4]·6H2O
Mr1047.45
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.9853 (6), 10.8365 (7), 28.974 (2)
β (°) 95.123 (1)
V3)2497.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.61
Crystal size (mm)0.32 × 0.28 × 0.22
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.828, 0.877
No. of measured, independent and
observed [I > 2σ(I)] reflections
16593, 5891, 4473
Rint0.023
(sin θ/λ)max1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.093, 1.05
No. of reflections5891
No. of parameters313
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.29

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 2005), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Cu1—N42.0196 (13)Cu1—Cl12.7738 (5)
Cu1—N12.0370 (13)
N4—Cu1—N190.89 (5)N4i—Cu1—N189.11 (5)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N2ii0.852.052.888 (2)169
O3—H3B···Cl10.852.343.1853 (17)170
O4—H4A···Cl1iii0.852.313.1469 (18)170
O4—H4B···O50.852.052.807 (3)147
O5—H5A···O4iv0.842.202.825 (3)131
O5—H5B···O30.842.052.837 (3)155
C9—H9···Cl1v0.932.813.732 (2)169
Symmetry codes: (ii) x, y1, z; (iii) x+1, y, z; (iv) x+1, y, z; (v) x, y+1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds