Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, [CuCl(C10H12N2O3)2]Cl·0.5H2O, is composed of discrete complex cations, Cl- anions and water mol­ecules. The O atom of the water mol­ecule lies on a twofold rotation axis. The [CuN4Cl] coordination polyhedron is intermediate between square pyramidal and trigonal bipy­ramidal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001633/bm1397sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001633/bm1397Isup2.hkl
Contains datablock I

CCDC reference: 145527

Comment top

The oxazole ring shows an interesting structure and is present in a wide variety of compounds which are of interest in many fields of application (Frump, 1971). The preparation of 2-substituted-2-oxazolines, involving heterocyclic ring-forming processes between nitriles and aminoalcohols, is higly desirable (Brunner & Oberman, 1989; Bolm et al., 1991). The formation of some new 2-pyridinyl-2-oxazolines and their NiII, CoII and CuII have been reported (Segĺa & Jamnický, 1993; Segĺa et al., 1998). \sch

The CuII centre is five-coordinated by four N donors from two ligands and by and a chloride ligand (Fig. 1). The coordination polyhedron around the CuII is intermediate between square-pyramidal and trigonal bipyramidal, and is very similar to that in [CuBr(L)2]Br.1/2H2O (Segĺa et al., 1998)·The τ parameter for both complexes is 0.48 (Addison et al., 1984). The Cu—N bond distances in the title complex (see Table 2) are similar to those in the analogues [CuBr(L)2]Br.1/2H2O complex [Cu—N1 = 2.018 (4), Cu—N2 = 2.093 (4), Cu—N3 = 2.001 (4), Cu—N4 = 2.201 (5) Å] (Segĺa et al., 1998). The two ligands L in [CuCl(L)2]+ are almost perpendicular, the dihedral angle between the N1,N2,C5,C6,Cu1 and N3,N4,C15,C16,Cu1 planes being 83.44 (6)°. The –OH group (O3—H12) on one oxazoline ring is disordered over two positions with occupation parameters 0.75 for O3—H12 and 0.25 for O3a—H12a (Fig. 1). The chloride anion linked by hydrogen bonds [Cl2···H11 2.30, Cl2···H25i 2.16 and Cl2···H24ii 2.31 Å; symmetry codes: (i) -x, y, 1/2 - z; (ii) 1/2 + x, 1/2 - y, 1/2 + z]. The O7 atom of water molecule is bonded by hydrogen bond to H23 (O7···H23 1.97 Å].

Experimental top

The title compound was obtained by an analogous reaction to that described by Segĺa et al. (1998). Equimolar quantities of pyridine-2-carbonitrile and 2-amino-2-hydroxymethyl-1,3-propandiol were added to an ethanolic solution of anhydrous copper(II) chloride and the mixture was heated for 30 min. at 333 K. After several days blue-green crystals of the title complex appeared. The density of the crystals was measured by flotation in C6H6/CHBr3

Refinement top

The H atoms on C10 corresponding to the minor disorder component of O3 have not been included. With the exception of H25 (on water oxygen O7) which was located from a ΔF synthesis and refined as part of a rigid rotating group, other H atoms were placed geometrically and refined as part of a riding model.

Computing details top

Data collection: SYNTEX P21 software (Syntex, 1973); cell refinement: SYNTEX P21 software; data reduction: XP21 (Pavelčík, 1993); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the title complex cation with displacement ellipsoids drawn at the 30% probability level and H atoms shown as spheres of arbitary radii.
(I) top
Crystal data top
[CuCl(C10H12N2O3)2]Cl·0.5H2OF(000) = 2304
Mr = 559.88Dx = 1.621 Mg m3
Dm = 1.62 Mg m3
Dm measured by flotation in C6 H6 /CHBr3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 17.995 (4) ÅCell parameters from 25 reflections
b = 16.601 (3) Åθ = 4.1–11.2°
c = 16.879 (3) ŵ = 1.23 mm1
β = 114.52 (3)°T = 293 K
V = 4587.6 (15) Å3Rectanglular prism, green-blue
Z = 80.45 × 0.40 × 0.35 mm
Data collection top
Syntex P21
diffractometer
3284 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.6°, θmin = 2.7°
θ–2θ scansh = 220
Absorption correction: ψ scan
(North et al., 1968)
k = 2121
Tmin = 0.565, Tmax = 0.650l = 1920
5869 measured reflections3 standard reflections every 100 reflections
5109 independent reflections intensity decay: 15%
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.052H atoms treated by a mixture of independent and constrained refinement
S = 0.80 w = 1/[σ2(Fo2) + (0.0057P)2]
where P = (Fo2 + 2Fc2)/3
5109 reflections(Δ/σ)max = 0.001
323 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
[CuCl(C10H12N2O3)2]Cl·0.5H2OV = 4587.6 (15) Å3
Mr = 559.88Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.995 (4) ŵ = 1.23 mm1
b = 16.601 (3) ÅT = 293 K
c = 16.879 (3) Å0.45 × 0.40 × 0.35 mm
β = 114.52 (3)°
Data collection top
Syntex P21
diffractometer
3284 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.021
Tmin = 0.565, Tmax = 0.6503 standard reflections every 100 reflections
5869 measured reflections intensity decay: 15%
5109 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.052H atoms treated by a mixture of independent and constrained refinement
S = 0.80Δρmax = 0.22 e Å3
5109 reflectionsΔρmin = 0.19 e Å3
323 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.356922 (14)0.104912 (13)0.198051 (14)0.03098 (7)
Cl10.42411 (3)0.08467 (4)0.11286 (3)0.04889 (14)
Cl20.10685 (4)0.18092 (4)0.39398 (4)0.06162 (17)
N10.36596 (9)0.13075 (9)0.32205 (9)0.0301 (3)
N20.38332 (9)0.00537 (9)0.24976 (10)0.0318 (3)
N30.32367 (9)0.21452 (9)0.14967 (9)0.0308 (3)
N40.22298 (9)0.08912 (9)0.13065 (9)0.0300 (3)
O10.38145 (10)0.06855 (8)0.44558 (9)0.0496 (4)
O20.21160 (10)0.19540 (11)0.28777 (10)0.0600 (5)
H110.18940.18640.32060.090*
O30.44344 (13)0.29216 (11)0.33916 (13)0.0467 (5)
H120.42280.33710.33280.070*
O40.11210 (8)0.16540 (8)0.06359 (9)0.0412 (3)
O50.08787 (10)0.04141 (9)0.18939 (11)0.0561 (4)
H230.05970.01700.20920.084*
O60.15628 (14)0.01503 (10)0.01738 (11)0.0720 (5)
H240.15180.05490.04770.108*
O70.00000.05976 (14)0.25000.0603 (6)
C10.39217 (12)0.07214 (12)0.21115 (14)0.0400 (5)
H10.38570.06950.15360.060*
C20.41068 (13)0.14525 (12)0.25373 (16)0.0466 (5)
H20.41520.19140.22480.070*
C30.42233 (14)0.14912 (12)0.33864 (16)0.0492 (6)
H30.43540.19780.36850.074*
C40.41451 (13)0.08016 (12)0.37976 (14)0.0437 (5)
H40.42320.08120.43810.066*
C50.39366 (12)0.01028 (11)0.33315 (12)0.0324 (4)
C60.38038 (12)0.06632 (11)0.36631 (12)0.0337 (4)
C70.35671 (16)0.14969 (13)0.45558 (13)0.0486 (6)
H50.39450.17320.51010.073*
H60.30230.14980.45430.073*
C80.35815 (12)0.19637 (11)0.37763 (12)0.0355 (4)
C90.27991 (13)0.24441 (13)0.33002 (14)0.0447 (5)
H70.27040.27850.37160.067*
H80.28690.27920.28750.067*
C100.43249 (15)0.25122 (14)0.40739 (15)0.0425 (5)
H90.4326 (14)0.2891 (15)0.4537 (15)0.064*
H100.476 (2)0.219 (3)0.429 (2)0.064*
C110.37448 (12)0.27394 (12)0.15350 (12)0.0392 (5)
H130.43050.26490.18110.059*
C120.34660 (14)0.34856 (12)0.11776 (13)0.0439 (5)
H140.38350.38960.12300.066*
C130.26472 (14)0.36203 (12)0.07465 (13)0.0433 (5)
H150.24520.41210.05020.065*
C140.21175 (13)0.30052 (11)0.06804 (12)0.0361 (4)
H160.15570.30780.03810.054*
C150.24292 (11)0.22783 (11)0.10638 (11)0.0297 (4)
C160.19268 (11)0.15710 (11)0.10159 (11)0.0295 (4)
C170.07959 (13)0.08561 (12)0.06456 (15)0.0462 (5)
H170.05030.06540.00580.069*
H180.04290.08640.09340.069*
C180.15466 (11)0.03362 (11)0.11517 (12)0.0340 (4)
C190.15784 (14)0.00491 (14)0.20188 (13)0.0456 (5)
H190.20650.02740.23140.068*
H200.16080.05100.23830.068*
C200.16141 (14)0.03892 (12)0.06383 (13)0.0443 (5)
H210.21310.06590.09580.066*
H220.11780.07660.05630.066*
H250.02000.10170.20060.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03417 (12)0.02802 (11)0.03326 (12)0.00355 (11)0.01649 (9)0.00244 (10)
Cl10.0500 (3)0.0590 (4)0.0491 (3)0.0140 (3)0.0319 (3)0.0091 (2)
Cl20.0919 (5)0.0457 (3)0.0587 (3)0.0012 (3)0.0426 (4)0.0067 (3)
N10.0315 (9)0.0276 (8)0.0301 (8)0.0019 (7)0.0117 (7)0.0026 (6)
N20.0300 (9)0.0290 (8)0.0368 (8)0.0012 (7)0.0142 (7)0.0014 (7)
N30.0347 (9)0.0291 (8)0.0291 (8)0.0022 (7)0.0139 (7)0.0010 (6)
N40.0297 (8)0.0259 (8)0.0346 (8)0.0021 (6)0.0136 (7)0.0007 (6)
O10.0795 (11)0.0375 (8)0.0364 (7)0.0095 (8)0.0286 (8)0.0063 (6)
O20.0449 (9)0.0682 (11)0.0672 (11)0.0007 (9)0.0237 (8)0.0236 (9)
O30.0551 (13)0.0353 (11)0.0600 (12)0.0007 (10)0.0342 (10)0.0031 (10)
O40.0286 (7)0.0343 (7)0.0560 (8)0.0009 (6)0.0129 (7)0.0074 (7)
O50.0654 (11)0.0415 (9)0.0796 (11)0.0159 (8)0.0484 (9)0.0043 (8)
O60.1229 (16)0.0464 (10)0.0614 (11)0.0230 (11)0.0530 (11)0.0098 (8)
O70.0638 (15)0.0579 (15)0.0659 (14)0.0000.0337 (12)0.000
C10.0390 (11)0.0350 (11)0.0483 (12)0.0003 (9)0.0204 (10)0.0096 (9)
C20.0441 (13)0.0275 (11)0.0751 (15)0.0035 (10)0.0315 (12)0.0109 (11)
C30.0538 (14)0.0271 (11)0.0725 (16)0.0016 (10)0.0318 (12)0.0071 (10)
C40.0518 (13)0.0313 (10)0.0483 (12)0.0007 (10)0.0211 (10)0.0064 (9)
C50.0297 (10)0.0298 (10)0.0376 (10)0.0002 (8)0.0138 (8)0.0012 (8)
C60.0378 (11)0.0320 (11)0.0304 (9)0.0016 (9)0.0135 (9)0.0020 (8)
C70.0708 (16)0.0390 (12)0.0412 (11)0.0045 (11)0.0282 (11)0.0055 (9)
C80.0436 (12)0.0308 (10)0.0338 (10)0.0039 (9)0.0176 (9)0.0069 (8)
C90.0443 (12)0.0402 (12)0.0523 (12)0.0105 (10)0.0227 (10)0.0062 (10)
C100.0460 (13)0.0349 (12)0.0435 (12)0.0051 (10)0.0154 (11)0.0059 (10)
C110.0397 (12)0.0399 (11)0.0395 (11)0.0101 (9)0.0180 (10)0.0005 (9)
C120.0580 (15)0.0369 (12)0.0394 (11)0.0141 (11)0.0229 (11)0.0020 (9)
C130.0616 (15)0.0279 (10)0.0418 (11)0.0009 (10)0.0228 (11)0.0033 (9)
C140.0399 (11)0.0310 (10)0.0376 (10)0.0028 (9)0.0165 (9)0.0024 (8)
C150.0342 (10)0.0287 (9)0.0280 (9)0.0014 (8)0.0146 (8)0.0013 (8)
C160.0292 (10)0.0301 (10)0.0285 (9)0.0002 (8)0.0111 (8)0.0002 (8)
C170.0342 (11)0.0354 (12)0.0627 (13)0.0062 (9)0.0138 (10)0.0056 (10)
C180.0277 (10)0.0303 (10)0.0414 (10)0.0061 (8)0.0117 (9)0.0003 (8)
C190.0469 (13)0.0456 (12)0.0469 (12)0.0098 (11)0.0222 (10)0.0016 (10)
C200.0523 (13)0.0311 (11)0.0504 (12)0.0085 (10)0.0222 (11)0.0037 (9)
Geometric parameters (Å, º) top
Cu1—N31.9825 (15)O5—C191.415 (2)
Cu1—N21.9988 (15)O6—C201.393 (2)
Cu1—N12.0757 (15)C1—C21.379 (3)
Cu1—N42.2127 (17)C2—C31.361 (3)
Cu1—Cl12.2552 (7)C3—C41.376 (3)
N1—C61.268 (2)C4—C51.364 (3)
N1—C81.482 (2)C5—C61.449 (3)
N2—C11.329 (2)C7—C81.536 (3)
N2—C51.343 (2)C8—C91.525 (3)
N3—C111.328 (2)C8—C101.521 (3)
N3—C151.346 (2)C11—C121.378 (3)
N4—C161.261 (2)C12—C131.364 (3)
N4—C181.470 (2)C13—C141.369 (3)
O1—C61.331 (2)C14—C151.374 (2)
O1—C71.450 (2)C15—C161.464 (3)
O2—C91.398 (3)C17—C181.530 (3)
O3—C101.420 (3)C18—C201.518 (3)
O4—C161.327 (2)C18—C191.517 (3)
O4—C171.451 (2)
N3—Cu1—N2175.54 (6)N1—C6—O1118.87 (17)
N3—Cu1—N196.29 (6)N1—C6—C5122.62 (16)
N2—Cu1—N181.03 (6)O1—C6—C5118.49 (16)
N3—Cu1—N479.56 (6)O1—C7—C8104.69 (15)
N2—Cu1—N497.28 (6)N1—C8—C9111.12 (15)
N1—Cu1—N498.96 (6)N1—C8—C10110.34 (17)
N3—Cu1—Cl191.38 (5)C9—C8—C10110.73 (17)
N2—Cu1—Cl192.80 (5)N1—C8—C7102.19 (15)
N1—Cu1—Cl1146.65 (5)C9—C8—C7112.03 (18)
N4—Cu1—Cl1114.35 (5)C10—C8—C7110.14 (17)
C6—N1—C8107.28 (14)O2—C9—C8112.86 (18)
C6—N1—Cu1109.32 (12)O3—C10—C8114.70 (19)
C8—N1—Cu1143.32 (12)N3—C11—C12121.87 (19)
C1—N2—C5118.07 (16)C13—C12—C11119.8 (2)
C1—N2—Cu1127.24 (13)C12—C13—C14118.84 (19)
C5—N2—Cu1114.68 (12)C13—C14—C15118.83 (19)
C11—N3—C15118.07 (16)N3—C15—C14122.50 (17)
C11—N3—Cu1125.28 (13)N3—C15—C16113.65 (16)
C15—N3—Cu1116.58 (12)C14—C15—C16123.81 (17)
C16—N4—C18107.27 (15)N4—C16—O4119.37 (16)
C16—N4—Cu1107.27 (12)N4—C16—C15122.62 (17)
C18—N4—Cu1144.85 (12)O4—C16—C15118.00 (16)
C6—O1—C7105.41 (14)O4—C17—C18104.75 (15)
C16—O4—C17105.34 (14)N4—C18—C20109.84 (16)
N2—C1—C2122.07 (19)N4—C18—C19109.35 (15)
C3—C2—C1119.24 (19)C20—C18—C19108.75 (16)
C2—C3—C4119.3 (2)N4—C18—C17103.01 (15)
C5—C4—C3118.54 (19)C20—C18—C17112.96 (17)
N2—C5—C4122.77 (18)C19—C18—C17112.76 (18)
N2—C5—C6112.22 (16)O5—C19—C18110.61 (17)
C4—C5—C6125.01 (17)O6—C20—C18110.35 (17)

Experimental details

Crystal data
Chemical formula[CuCl(C10H12N2O3)2]Cl·0.5H2O
Mr559.88
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)17.995 (4), 16.601 (3), 16.879 (3)
β (°) 114.52 (3)
V3)4587.6 (15)
Z8
Radiation typeMo Kα
µ (mm1)1.23
Crystal size (mm)0.45 × 0.40 × 0.35
Data collection
DiffractometerSyntex P21
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.565, 0.650
No. of measured, independent and
observed [I > 2σ(I)] reflections
5869, 5109, 3284
Rint0.021
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.052, 0.80
No. of reflections5109
No. of parameters323
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.19

Computer programs: SYNTEX P21 software (Syntex, 1973), SYNTEX P21 software, XP21 (Pavelčík, 1993), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1965), SHELXL97.

Selected geometric parameters (Å, º) top
Cu1—N31.9825 (15)Cu1—N42.2127 (17)
Cu1—N21.9988 (15)Cu1—Cl12.2552 (7)
Cu1—N12.0757 (15)
N3—Cu1—N2175.54 (6)N1—Cu1—N498.96 (6)
N3—Cu1—N196.29 (6)N3—Cu1—Cl191.38 (5)
N2—Cu1—N181.03 (6)N2—Cu1—Cl192.80 (5)
N3—Cu1—N479.56 (6)N1—Cu1—Cl1146.65 (5)
N2—Cu1—N497.28 (6)N4—Cu1—Cl1114.35 (5)
 

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