Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101006060/gd1148sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101006060/gd1148Isup2.hkl |
CCDC reference: 170161
For related literature, see: Addison et al. (1989); Bkouche-Waksman, Barbe & Kvick (1988); Capasso et al. (1974); Kvick et al. (1980); Legros & Kvick (1980); Longenecker & Snell (1957); Metzler et al. (1954); Ueki et al. (1967, 1968, 1969); Warda (1997); Warda et al. (1996).
An ethanol solution (50 ml) of glycine (1 mmol, 0.07 g) and 2-hydroxy-1-naphthaldehyde (1 mmol, 0.17 g) was kept at 343 K in a reflux condenser for 30 min. An ethanol solution (50 ml) of CuCl2·2H2O (1 mmol, 0.17 g) was then added, and the temperature of the solution was readjusted to 343 K and kept constant for the next 30 min. The resulting dark-green solution was filtered and allowed to evaporate slowly. After two weeks, green needle-shaped crystals were obtained. Analysis, calculated for C13H9NO3Cu·H2O: C 46.6, H 3.6, N 4.5%; found: C 46.7, H 3.6, N 4.6%.
All H atoms were included at calculated positions and refined using a riding model, with isotropic displacement parameters equal to 1.5Ueq of the parent C or O atom, and with C—H = 0.93–0.97 Å and O—H = 0.96 Å.
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XDISK in SHELXTL/PC (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.
C13H11CuNO4 | F(000) = 628 |
Mr = 308.78 | Dx = 1.751 Mg m−3 Dm = 1.70 (2) Mg m−3 Dm measured by measured by flotation in CH3I/CCl4 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 15 reflections |
a = 7.043 (1) Å | θ = 10–20° |
b = 28.741 (6) Å | µ = 1.87 mm−1 |
c = 5.940 (1) Å | T = 293 K |
β = 103.06 (3)° | Needle, dark green |
V = 1171.3 (4) Å3 | 0.4 × 0.1 × 0.1 mm |
Z = 4 |
Siemens P3 diffractometer | 1740 reflections with I > 2σ(I) |
Radiation source: FK60-10 Siemens Mo tube | Rint = 0.034 |
Graphite monochromator | θmax = 30.1°, θmin = 2.8° |
ω/2θ scans | h = −9→9 |
Absorption correction: ψ-scan (North et al., 1968) | k = −40→40 |
Tmin = 0.723, Tmax = 0.856 | l = −8→8 |
3771 measured reflections | 2 standard reflections every 100 reflections |
1885 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.099 | Calculated w = 1/[σ2(Fo2) + (0.05P)2 + 1.9P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1885 reflections | Δρmax = 0.45 e Å−3 |
172 parameters | Δρmin = −1.13 e Å−3 |
2 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (2) |
C13H11CuNO4 | V = 1171.3 (4) Å3 |
Mr = 308.78 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 7.043 (1) Å | µ = 1.87 mm−1 |
b = 28.741 (6) Å | T = 293 K |
c = 5.940 (1) Å | 0.4 × 0.1 × 0.1 mm |
β = 103.06 (3)° |
Siemens P3 diffractometer | 1740 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (North et al., 1968) | Rint = 0.034 |
Tmin = 0.723, Tmax = 0.856 | 2 standard reflections every 100 reflections |
3771 measured reflections | intensity decay: none |
1885 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.099 | Δρmax = 0.45 e Å−3 |
S = 1.06 | Δρmin = −1.13 e Å−3 |
1885 reflections | Absolute structure: Flack (1983) |
172 parameters | Absolute structure parameter: −0.01 (2) |
2 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.78545 (10) | 0.04439 (2) | 0.16419 (11) | 0.0312 (1) | |
O1 | 0.6529 (4) | 0.07120 (12) | 0.3798 (7) | 0.0356 (10) | |
O2 | 0.9124 (4) | 0.02549 (12) | −0.0812 (5) | 0.0318 (8) | |
O3 | 0.5508 (4) | 0.00809 (12) | 0.0488 (6) | 0.0342 (9) | |
O4 | 1.1968 (5) | 0.03206 (15) | −0.1836 (7) | 0.0431 (10) | |
N1 | 1.0062 (5) | 0.08349 (13) | 0.2684 (7) | 0.0306 (10) | |
C1 | 0.8936 (7) | 0.12650 (15) | 0.5623 (9) | 0.0321 (11) | |
C2 | 0.7151 (6) | 0.10279 (14) | 0.5372 (8) | 0.0309 (11) | |
C3 | 0.5913 (7) | 0.11218 (17) | 0.6897 (10) | 0.0387 (12) | |
C4 | 0.6414 (8) | 0.14404 (19) | 0.8592 (10) | 0.0429 (17) | |
C5 | 0.8680 (10) | 0.20232 (19) | 1.0722 (11) | 0.0519 (19) | |
C6 | 1.0379 (12) | 0.2264 (2) | 1.1062 (12) | 0.061 (2) | |
C7 | 1.1644 (11) | 0.2190 (2) | 0.9593 (12) | 0.0589 (19) | |
C8 | 1.1204 (9) | 0.18765 (19) | 0.7809 (11) | 0.0480 (17) | |
C9 | 0.9443 (7) | 0.16155 (15) | 0.7420 (9) | 0.0371 (11) | |
C10 | 0.8171 (8) | 0.16992 (16) | 0.8902 (9) | 0.0391 (14) | |
C11 | 1.0290 (6) | 0.11513 (15) | 0.4238 (9) | 0.0344 (11) | |
C12 | 1.1575 (6) | 0.07450 (17) | 0.1417 (9) | 0.0343 (11) | |
C13 | 1.0858 (6) | 0.04143 (15) | −0.0556 (8) | 0.0315 (11) | |
H2A | 0.43784 | 0.02350 | −0.04170 | 0.0513* | |
H2B | 0.59054 | −0.01480 | −0.04970 | 0.0513* | |
H3 | 0.47417 | 0.09617 | 0.67253 | 0.0579* | |
H4 | 0.55871 | 0.14921 | 0.95856 | 0.0643* | |
H5 | 0.78401 | 0.20727 | 1.17025 | 0.0782* | |
H6 | 1.06997 | 0.24767 | 1.22678 | 0.0920* | |
H7 | 1.28042 | 0.23566 | 0.98276 | 0.0881* | |
H8 | 1.20642 | 0.18341 | 0.68467 | 0.0718* | |
H11 | 1.14382 | 0.13228 | 0.44893 | 0.0513* | |
H12A | 1.27101 | 0.06133 | 0.24579 | 0.0517* | |
H12B | 1.19616 | 0.10358 | 0.08223 | 0.0517* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0227 (2) | 0.0399 (2) | 0.0315 (2) | −0.0032 (3) | 0.0073 (2) | −0.0058 (3) |
O1 | 0.0256 (14) | 0.0389 (16) | 0.0430 (19) | −0.0040 (12) | 0.0095 (13) | −0.0084 (14) |
O2 | 0.0240 (13) | 0.0460 (17) | 0.0248 (13) | −0.0009 (12) | 0.0045 (11) | −0.0037 (13) |
O3 | 0.0217 (12) | 0.0434 (17) | 0.0352 (16) | −0.0005 (11) | 0.0019 (12) | −0.0094 (14) |
O4 | 0.0267 (14) | 0.066 (2) | 0.0378 (18) | 0.0039 (15) | 0.0097 (13) | −0.0065 (17) |
N1 | 0.0244 (15) | 0.0334 (17) | 0.0332 (18) | −0.0020 (13) | 0.0047 (14) | 0.0007 (15) |
C1 | 0.033 (2) | 0.0291 (18) | 0.034 (2) | 0.0020 (16) | 0.0074 (19) | 0.0023 (18) |
C2 | 0.0309 (19) | 0.0306 (19) | 0.0306 (19) | 0.0036 (15) | 0.0056 (16) | −0.0005 (16) |
C3 | 0.037 (2) | 0.040 (2) | 0.041 (2) | 0.0041 (19) | 0.013 (2) | −0.007 (2) |
C4 | 0.044 (3) | 0.047 (3) | 0.038 (3) | 0.010 (2) | 0.010 (2) | −0.003 (2) |
C5 | 0.071 (4) | 0.040 (3) | 0.043 (3) | 0.004 (3) | 0.009 (3) | −0.008 (2) |
C6 | 0.090 (5) | 0.045 (3) | 0.047 (3) | −0.010 (3) | 0.012 (3) | −0.014 (3) |
C7 | 0.070 (4) | 0.047 (3) | 0.054 (3) | −0.021 (3) | 0.002 (3) | −0.008 (3) |
C8 | 0.054 (3) | 0.043 (3) | 0.046 (3) | −0.011 (2) | 0.009 (2) | −0.005 (2) |
C9 | 0.042 (2) | 0.0288 (19) | 0.038 (2) | 0.0022 (17) | 0.0041 (19) | −0.0026 (18) |
C10 | 0.051 (3) | 0.031 (2) | 0.034 (2) | 0.0069 (18) | 0.007 (2) | 0.0002 (18) |
C11 | 0.0276 (18) | 0.0307 (19) | 0.043 (2) | −0.0022 (15) | 0.0040 (17) | −0.0010 (18) |
C12 | 0.0244 (17) | 0.042 (2) | 0.037 (2) | 0.0000 (15) | 0.0080 (16) | −0.0039 (18) |
C13 | 0.0229 (17) | 0.039 (2) | 0.031 (2) | 0.0056 (15) | 0.0026 (15) | 0.0032 (17) |
Cu1—O1 | 1.909 (4) | C4—C10 | 1.420 (8) |
Cu1—O2 | 1.951 (3) | C5—C10 | 1.410 (8) |
Cu1—O3 | 1.944 (3) | C5—C6 | 1.357 (10) |
Cu1—N1 | 1.905 (4) | C6—C7 | 1.397 (11) |
Cu1—O2i | 2.551 (3) | C7—C8 | 1.372 (9) |
O1—C2 | 1.306 (6) | C8—C9 | 1.423 (8) |
O2—C13 | 1.281 (5) | C9—C10 | 1.411 (8) |
O4—C13 | 1.237 (6) | C12—C13 | 1.505 (7) |
O3—H2A | 0.9617 | C3—H3 | 0.9299 |
O3—H2B | 0.9631 | C4—H4 | 0.9300 |
N1—C12 | 1.460 (6) | C5—H5 | 0.9301 |
N1—C11 | 1.280 (6) | C6—H6 | 0.9299 |
C1—C9 | 1.452 (7) | C7—H7 | 0.9300 |
C1—C11 | 1.431 (7) | C8—H8 | 0.9301 |
C1—C2 | 1.408 (7) | C11—H11 | 0.9299 |
C2—C3 | 1.418 (7) | C12—H12A | 0.9702 |
C3—C4 | 1.348 (8) | C12—H12B | 0.9700 |
Cu1···O4 | 3.936 (4) | C10···C11vi | 3.552 (7) |
Cu1···C2ii | 4.012 (5) | C11···C5ii | 3.295 (8) |
Cu1···C3ii | 3.445 (6) | C11···C10ii | 3.552 (7) |
Cu1···C4ii | 3.418 (6) | C11···O4vi | 3.360 (6) |
Cu1···C10ii | 3.985 (5) | C12···O4i | 3.225 (7) |
Cu1···O3iii | 3.955 (4) | C12···C9ii | 3.541 (7) |
Cu1···O3i | 3.454 (3) | C13···O3v | 3.333 (5) |
Cu1···O1iii | 3.748 (4) | C13···C2ii | 3.595 (6) |
Cu1···O4i | 3.585 (4) | C13···C1ii | 3.402 (7) |
Cu1···H3ii | 3.5576 | C13···O4i | 3.029 (6) |
Cu1···H4ii | 3.4981 | C2···H2Bi | 2.6883 |
Cu1···H2Bi | 2.5594 | C5···H6vii | 2.9556 |
O1···Cu1i | 3.748 (4) | C7···H5viii | 2.9668 |
O1···O3i | 2.654 (5) | C8···H11 | 2.5681 |
O2···C2ii | 3.253 (5) | C8···H12Bvi | 2.9825 |
O2···O4i | 3.192 (5) | C9···H12Bvi | 2.8960 |
O3···C13iv | 3.333 (5) | C10···H6vii | 2.9695 |
O3···O1iii | 2.654 (5) | C11···H8 | 2.6341 |
O3···O4iv | 2.653 (5) | C12···H2Av | 2.8646 |
O3···C2iii | 3.396 (5) | C13···H2Av | 2.5154 |
O3···Cu1iii | 3.454 (3) | H2A···O4iv | 1.7339 |
O3···Cu1i | 3.955 (4) | H2A···C12iv | 2.8646 |
O3···O3iii | 3.006 (5) | H2A···C13iv | 2.5154 |
O3···O3i | 3.006 (5) | H2A···H12Aiv | 2.5270 |
O4···O2iii | 3.192 (5) | H2A···O3iii | 2.8720 |
O4···C11ii | 3.360 (6) | H2B···Cu1iii | 2.5594 |
O4···O3v | 2.653 (5) | H2B···O1iii | 1.7547 |
O4···C12iii | 3.225 (7) | H2B···O3iii | 2.3456 |
O4···Cu1 | 3.936 (4) | H2B···C2iii | 2.6883 |
O4···Cu1iii | 3.585 (4) | H3···Cu1vi | 3.5576 |
O4···C13iii | 3.029 (6) | H4···Cu1vi | 3.4981 |
O1···H2Bi | 1.7547 | H4···H5 | 2.4458 |
O1···H12Aiv | 2.6421 | H5···H4 | 2.4458 |
O3···H2Bi | 2.3456 | H5···C7ix | 2.9668 |
O3···H2Ai | 2.8720 | H5···H7ix | 2.4816 |
O4···H2Av | 1.7339 | H6···C5x | 2.9556 |
O4···H12Aiii | 2.7844 | H6···C10x | 2.9695 |
N1···C10ii | 3.412 (6) | H7···H5viii | 2.4816 |
C1···C13vi | 3.402 (7) | H8···C11 | 2.6341 |
C2···Cu1vi | 4.012 (5) | H8···H11 | 2.0089 |
C2···O2vi | 3.253 (5) | H11···C8 | 2.5681 |
C2···C13vi | 3.595 (6) | H11···H8 | 2.0089 |
C2···O3i | 3.396 (5) | H11···H12B | 2.4339 |
C3···Cu1vi | 3.445 (6) | H12A···O1v | 2.6421 |
C4···Cu1vi | 3.418 (6) | H12A···H2Av | 2.5270 |
C5···C11vi | 3.295 (8) | H12A···O4i | 2.7844 |
C9···C12vi | 3.541 (7) | H12B···C8ii | 2.9825 |
C10···N1vi | 3.412 (6) | H12B···C9ii | 2.8960 |
C10···Cu1vi | 3.985 (5) | H12B···H11 | 2.4339 |
O1—Cu1—O2 | 171.62 (15) | C7—C8—C9 | 120.5 (6) |
O1—Cu1—O3 | 86.99 (14) | C1—C9—C8 | 123.1 (5) |
O1—Cu1—N1 | 91.77 (16) | C1—C9—C10 | 119.4 (4) |
O1—Cu1—O2i | 94.53 (13) | C8—C9—C10 | 117.5 (5) |
O2—Cu1—O3 | 94.80 (14) | C4—C10—C5 | 120.6 (5) |
O2—Cu1—N1 | 85.92 (15) | C4—C10—C9 | 119.2 (5) |
O2—Cu1—O2i | 93.74 (12) | C5—C10—C9 | 120.2 (5) |
O3—Cu1—N1 | 176.23 (16) | N1—C11—C1 | 125.8 (4) |
O2i—Cu1—O3 | 86.71 (13) | N1—C12—C13 | 111.0 (4) |
O2i—Cu1—N1 | 96.94 (14) | O2—C13—O4 | 124.6 (4) |
Cu1—O1—C2 | 128.7 (3) | O2—C13—C12 | 117.5 (4) |
Cu1—O2—C13 | 113.4 (3) | O4—C13—C12 | 117.9 (4) |
Cu1—O2—Cu1iii | 120.24 (14) | C2—C3—H3 | 119.61 |
Cu1iii—O2—C13 | 123.3 (3) | C4—C3—H3 | 119.62 |
H2A—O3—H2B | 107.00 | C3—C4—H4 | 119.14 |
Cu1—O3—H2A | 118.69 | C10—C4—H4 | 119.11 |
Cu1—O3—H2B | 103.90 | C6—C5—H5 | 119.53 |
Cu1—N1—C11 | 127.9 (3) | C10—C5—H5 | 119.57 |
Cu1—N1—C12 | 111.4 (3) | C5—C6—H6 | 120.16 |
C11—N1—C12 | 120.7 (4) | C7—C6—H6 | 120.20 |
C2—C1—C9 | 118.6 (4) | C6—C7—H7 | 119.39 |
C2—C1—C11 | 121.6 (4) | C8—C7—H7 | 119.43 |
C9—C1—C11 | 119.7 (4) | C7—C8—H8 | 119.73 |
O1—C2—C3 | 115.8 (4) | C9—C8—H8 | 119.74 |
O1—C2—C1 | 124.0 (4) | N1—C11—H11 | 117.08 |
C1—C2—C3 | 120.2 (4) | C1—C11—H11 | 117.07 |
C2—C3—C4 | 120.8 (5) | N1—C12—H12A | 109.44 |
C3—C4—C10 | 121.8 (5) | N1—C12—H12B | 109.45 |
C6—C5—C10 | 120.9 (6) | C13—C12—H12A | 109.46 |
C5—C6—C7 | 119.6 (6) | C13—C12—H12B | 109.45 |
C6—C7—C8 | 121.2 (7) | H12A—C12—H12B | 108.03 |
O3—Cu1—O1—C2 | −179.3 (4) | Cu1—N1—C12—C13 | 7.4 (5) |
N1—Cu1—O1—C2 | −2.9 (4) | C11—N1—C12—C13 | −171.1 (4) |
O2i—Cu1—O1—C2 | 94.2 (4) | C9—C1—C11—N1 | 176.4 (5) |
O3—Cu1—O2—C13 | −176.3 (3) | C9—C1—C2—C3 | −1.9 (7) |
O3—Cu1—O2—Cu1iii | −15.42 (18) | C11—C1—C2—O1 | −4.4 (7) |
N1—Cu1—O2—C13 | 7.4 (3) | C11—C1—C2—C3 | 174.8 (5) |
N1—Cu1—O2—Cu1iii | 168.29 (19) | C9—C1—C2—O1 | 178.9 (4) |
O2i—Cu1—O2—C13 | −89.3 (3) | C2—C1—C11—N1 | −0.3 (8) |
O2i—Cu1—O2—Cu1iii | 71.59 (16) | C2—C1—C9—C10 | 1.9 (7) |
O1—Cu1—N1—C11 | −1.6 (4) | C11—C1—C9—C8 | 3.6 (7) |
O1—Cu1—N1—C12 | −180.0 (3) | C2—C1—C9—C8 | −179.6 (5) |
O2—Cu1—N1—C11 | 170.3 (4) | C11—C1—C9—C10 | −174.9 (4) |
O2—Cu1—N1—C12 | −8.0 (3) | C1—C2—C3—C4 | 0.5 (8) |
O2i—Cu1—N1—C11 | −96.4 (4) | O1—C2—C3—C4 | 179.8 (5) |
O2i—Cu1—N1—C12 | 85.2 (3) | C2—C3—C4—C10 | 1.0 (8) |
O1—Cu1—O2i—Cu1i | 20.93 (19) | C3—C4—C10—C5 | −178.6 (5) |
O1—Cu1—O2i—C13i | −138.0 (3) | C3—C4—C10—C9 | −1.0 (8) |
O2—Cu1—O2i—Cu1i | −160.40 (17) | C10—C5—C6—C7 | −0.1 (9) |
O2—Cu1—O2i—C13i | 40.7 (3) | C6—C5—C10—C9 | 0.9 (8) |
O3—Cu1—O2i—Cu1i | −65.79 (18) | C6—C5—C10—C4 | 178.5 (6) |
O3—Cu1—O2i—C13i | 135.3 (3) | C5—C6—C7—C8 | −0.2 (10) |
N1—Cu1—O2i—Cu1i | 113.26 (19) | C6—C7—C8—C9 | −0.4 (9) |
N1—Cu1—O2i—C13i | −45.6 (3) | C7—C8—C9—C1 | −177.3 (5) |
Cu1—O1—C2—C1 | 6.0 (7) | C7—C8—C9—C10 | 1.2 (8) |
Cu1—O1—C2—C3 | −173.2 (3) | C1—C9—C10—C4 | −0.4 (7) |
Cu1—O2—C13—O4 | 176.2 (4) | C8—C9—C10—C5 | −1.5 (7) |
Cu1iii—O2—C13—C12 | −165.1 (3) | C8—C9—C10—C4 | −179.0 (5) |
Cu1—O2—C13—C12 | −4.9 (5) | C1—C9—C10—C5 | 177.1 (5) |
Cu1iii—O2—C13—O4 | 16.0 (6) | N1—C12—C13—O4 | 177.3 (4) |
Cu1—N1—C11—C1 | 3.1 (7) | N1—C12—C13—O2 | −1.6 (6) |
C12—N1—C11—C1 | −178.6 (4) |
Symmetry codes: (i) x, −y, z+1/2; (ii) x, y, z−1; (iii) x, −y, z−1/2; (iv) x−1, y, z; (v) x+1, y, z; (vi) x, y, z+1; (vii) x−1/2, −y+1/2, z−1/2; (viii) x+1/2, −y+1/2, z−1/2; (ix) x−1/2, −y+1/2, z+1/2; (x) x+1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H2A···O4iv | 0.9617 | 1.7339 | 2.653 (5) | 159 |
O3—H2B···O1iii | 0.9631 | 1.7547 | 2.654 (5) | 154 |
O3—H2B···O3iii | 0.9631 | 2.3456 | 3.006 (5) | 125 |
Symmetry codes: (iii) x, −y, z−1/2; (iv) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H11CuNO4 |
Mr | 308.78 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 7.043 (1), 28.741 (6), 5.940 (1) |
β (°) | 103.06 (3) |
V (Å3) | 1171.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.87 |
Crystal size (mm) | 0.4 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Siemens P3 diffractometer |
Absorption correction | ψ-scan (North et al., 1968) |
Tmin, Tmax | 0.723, 0.856 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3771, 1885, 1740 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.099, 1.06 |
No. of reflections | 1885 |
No. of parameters | 172 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −1.13 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.01 (2) |
Computer programs: XSCANS (Siemens, 1996), XSCANS, XDISK in SHELXTL/PC (Sheldrick, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990), SHELXL97.
Cu1—O1 | 1.909 (4) | O1—C2 | 1.306 (6) |
Cu1—O2 | 1.951 (3) | O2—C13 | 1.281 (5) |
Cu1—O3 | 1.944 (3) | O4—C13 | 1.237 (6) |
Cu1—N1 | 1.905 (4) | N1—C12 | 1.460 (6) |
Cu1—O2i | 2.551 (3) | N1—C11 | 1.280 (6) |
O1—Cu1—O2 | 171.62 (15) | Cu1—O2—Cu1ii | 120.24 (14) |
O1—Cu1—O3 | 86.99 (14) | Cu1ii—O2—C13 | 123.3 (3) |
O1—Cu1—N1 | 91.77 (16) | Cu1—N1—C11 | 127.9 (3) |
O1—Cu1—O2i | 94.53 (13) | Cu1—N1—C12 | 111.4 (3) |
O2—Cu1—O3 | 94.80 (14) | C11—N1—C12 | 120.7 (4) |
O2—Cu1—N1 | 85.92 (15) | O1—C2—C3 | 115.8 (4) |
O2—Cu1—O2i | 93.74 (12) | O1—C2—C1 | 124.0 (4) |
O3—Cu1—N1 | 176.23 (16) | N1—C11—C1 | 125.8 (4) |
O2i—Cu1—O3 | 86.71 (13) | N1—C12—C13 | 111.0 (4) |
O2i—Cu1—N1 | 96.94 (14) | O2—C13—O4 | 124.6 (4) |
Cu1—O1—C2 | 128.7 (3) | O2—C13—C12 | 117.5 (4) |
Cu1—O2—C13 | 113.4 (3) | O4—C13—C12 | 117.9 (4) |
Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H2A···O4iii | 0.9617 | 1.7339 | 2.653 (5) | 159 |
O3—H2B···O1ii | 0.9631 | 1.7547 | 2.654 (5) | 154 |
O3—H2B···O3ii | 0.9631 | 2.3456 | 3.006 (5) | 125 |
Symmetry codes: (ii) x, −y, z−1/2; (iii) x−1, y, z. |
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Metal complexes of amino-acid Schiff bases have attracted attention as models for vitamin B6 and its analogues in catalyzed non-enzymatic transamination reactions in solution (Metzler et al., 1954; Longenecker & Snell, 1957). The general model assumes transfer of charge density from the α-C region of the amino-acid residue toward the more electronegative pyridine N atom. The metal atom can act as a catalyst by promoting the formation of a Schiff base and holding the planarity of the conjugated system by means of the formation of a chelate. Moreover, the metal ion increases the withdrawal of electrons from the α-C region. Several X-ray structural studies of the copper complexes of amino-acid Schiff bases have been published so far (Ueki et al., 1967, 1968, 1969; Bkouche-Waksman et al., 1988; Warda et al., 1996; Warda, 1997). The present paper describes a new example, the title compound, (I), which illustrates a different way of generating the polymeric chain (through the other carboxylic O atom) as compared with [aqua(N-salicylideneglycinato)]copper(II) hemihydrate (Bkouche-Waksman et al., 1988), (II). \sch
The CuII ion in (I) is five-coordinated (Table 1, Fig. 1) in the form of a slightly distorted square pyramid, with basal atoms O1, O2 and N1 of the Schiff base and O3 of the water molecule. The apical O2i [symmetry code: (i) x, -y, 1/2 + z] of a neighbouring molecule completes the coordination. The τ parameter of Addison et al. (1989) indicates a 7.5% trigonal bipyramidal distortion. The basal atoms deviate by up to 0.039 (4) Å from their least-squares plane and the CuII ion is likewise displaced by 0.099 (1) Å towards the apical donor.
The apical Cu—O2i bond [2.551 (3) Å] is long compared with the corresponding bond in (II) [2.308 (1) Å] and links the molecules to form polymeric chains propagated along the c axis, as indicated in Fig. 2. In these chains, Cu···Cu distances of 3.916 (1) and 5.940 (1) Å are found between nearest neighbour (c-glide related) and cell-translated CuII ions, respectively. The Cu—O1 and Cu—O2 bond lengths [1.909 (4) and 1.951 (3) Å, respectively] are consistent with more negative charge on the phenolic atom O1 than on the carboxylic atom O2, as noted by Capasso et al. (1974) and others.
The bond distances at C12, the α-C implicated in the catalytic activity of such complexes (see e.g. Bkouche-Waksman et al., 1988), i.e. Cα—Cβ and Cα—N, are 1.505 (7) and 1.460 (6) Å, respectively, in the present study, compared with 1.526 (1) and 1.455 (1) Å in (II). In the carboxylate group comprising atoms C13, O2 and O4, only O2 coordinates to the Cu, while O4 participates in hydrogen-bond formation (see below and Table 2). The resulting difference in C—O distances of 0.044 (6) Å is considerably larger than in (II), α-glycine (Legros & Kvick, 1980) or χ-glycine (Kvick et al., 1980) [0.022 (1), 0.002 (1) and 0.008 (1) Å, respectively].
As expected, the Cu coordination renders the conjugated system comprising atoms C12, N1, C11, C1 and C2 planar (within 2.5σ). The six-membered chelate ring Cu1/O1/C2/C1/C11/N1 is, however, only approximately planar (within 7σ). The naphthalene rings are planar within the 2.5σ range, with an angle of 1.4 (3)° between them. The chelate ring and the condensed naphthalene ring make an angle of 4.9 (2)°. The bonds and angles within the naphthalene moiety are in the ranges 1.348 (8)–1.452 (7) Å and 117.5 (5)–123.1 (5)°, respectively.
The formation of the chains and the packing of the molecules results in close intermolecular O4···C13ii and C5···C11iii contacts [3.029 (6) and 3.295 (8) Å, respectively; symmetry codes: (ii) x, -y, z - 1/2; (iii) x, y, 1 + z]. Both H atoms of the water molecule participate in hydrogen-bond formation (Table 2). The bond to O1 occurs within the polymeric chains (Fig. 1), but that to O4 occurs between chains, linking them into sheets parallel to [010].