In the title compound, [Cu(C4H5NO4)(C10H8N2)(H2O)]·5H2O, the CuII atom is coordinated by an N,O-bidentate L-aspartate dianion, a bipyridine ligand and a water molecule in a distorted square-pyramidal geometry. Intermolecular hydrogen bonds involving the non-coordinated water molecules help to consolidate the crystal packing.
Supporting information
CCDC reference: 608529
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.023
- wR factor = 0.063
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT731_ALERT_1_B Bond Calc 0.84(6), Rep 0.846(10) ...... 6.00 su-Rat
O9 -H18 1.555 1.555
PLAT735_ALERT_1_B D-H Calc 0.84(6), Rep 0.846(10) ...... 6.00 su-Rat
O9 -H18 1.555 1.555
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.64
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 11
PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.02 Ratio
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O6 - H16 ... 0.66 Ang.
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O8 - H21 ... 0.63 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
Aqua(
L-aspartato-
κ2N,
O)(2,2'-bipyridine-
κ2N,
N)copper(II) pentahydrate
top
Crystal data top
[Cu(C4H5NO4)(C10H8N2)(H2O)]·5H2O | F(000) = 956 |
Mr = 458.91 | Dx = 1.575 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5837 reflections |
a = 9.0194 (3) Å | θ = 2.3–27.4° |
b = 21.4430 (6) Å | µ = 1.19 mm−1 |
c = 10.0189 (3) Å | T = 273 K |
β = 93.088 (1)° | Block, blue |
V = 1934.9 (1) Å3 | 0.20 × 0.10 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3404 independent reflections |
Radiation source: fine-focus sealed tube | 3100 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.797, Tmax = 0.911 | k = −22→25 |
21692 measured reflections | l = −11→11 |
Refinement top
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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0343P)2 + 0.7615P] where P = (Fo2 + 2Fc2)/3 |
3404 reflections | (Δ/σ)max = 0.001 |
353 parameters | Δρmax = 0.25 e Å−3 |
1 restraint | Δρmin = −0.24 e Å−3 |
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 >
2σ(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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2834 (2) | 0.54216 (9) | 1.04546 (19) | 0.0353 (4) | |
C2 | 0.2630 (2) | 0.60181 (10) | 1.0931 (2) | 0.0422 (5) | |
C3 | 0.1498 (2) | 0.63753 (10) | 1.0363 (2) | 0.0449 (5) | |
C4 | 0.0596 (2) | 0.61347 (9) | 0.9340 (2) | 0.0397 (4) | |
C5 | 0.08520 (19) | 0.55369 (8) | 0.88975 (17) | 0.0297 (4) | |
C6 | −0.00209 (19) | 0.52279 (8) | 0.77916 (17) | 0.0303 (4) | |
C7 | −0.1235 (2) | 0.54951 (11) | 0.7105 (2) | 0.0469 (5) | |
C8 | −0.1965 (3) | 0.51606 (12) | 0.6093 (2) | 0.0534 (6) | |
C9 | −0.1480 (2) | 0.45769 (11) | 0.5779 (2) | 0.0471 (5) | |
C10 | −0.0271 (2) | 0.43364 (9) | 0.6496 (2) | 0.0391 (4) | |
C11 | 0.39340 (18) | 0.34863 (8) | 1.00320 (17) | 0.0302 (4) | |
C12 | 0.35137 (18) | 0.31592 (8) | 0.87079 (17) | 0.0271 (3) | |
C13 | 0.3349 (2) | 0.24565 (8) | 0.88384 (19) | 0.0296 (4) | |
C14 | 0.22592 (19) | 0.22565 (8) | 0.98616 (17) | 0.0300 (4) | |
Cu1 | 0.21685 (2) | 0.434252 (9) | 0.867035 (19) | 0.02695 (8) | |
H1 | 0.353 (2) | 0.5168 (9) | 1.0778 (19) | 0.031 (5)* | |
H2 | 0.324 (3) | 0.6152 (11) | 1.160 (2) | 0.053 (7)* | |
H3 | 0.137 (3) | 0.6768 (12) | 1.068 (2) | 0.054 (6)* | |
H4 | −0.014 (3) | 0.6351 (11) | 0.897 (2) | 0.050 (6)* | |
H5 | −0.154 (3) | 0.5889 (12) | 0.734 (2) | 0.052 (6)* | |
H6 | −0.280 (3) | 0.5332 (13) | 0.570 (3) | 0.074 (8)* | |
H7 | −0.196 (3) | 0.4327 (10) | 0.508 (3) | 0.054 (7)* | |
H8 | 0.008 (2) | 0.3932 (10) | 0.632 (2) | 0.044 (6)* | |
H9 | 0.404 (3) | 0.5063 (14) | 0.733 (3) | 0.059 (8)* | |
H10 | 0.428 (3) | 0.4529 (12) | 0.678 (3) | 0.051 (7)* | |
H11 | 0.147 (2) | 0.3287 (10) | 0.836 (2) | 0.033 (6)* | |
H13 | 0.434 (2) | 0.3241 (8) | 0.8172 (18) | 0.025 (4)* | |
H14 | 0.424 (2) | 0.2274 (10) | 0.908 (2) | 0.042 (6)* | |
H15 | 0.304 (2) | 0.2285 (9) | 0.803 (2) | 0.039 (5)* | |
H16 | 0.568 (3) | 0.3841 (13) | 0.240 (3) | 0.053 (9)* | |
H17 | 0.685 (5) | 0.377 (2) | 0.301 (5) | 0.16 (2)* | |
H19 | 0.885 (4) | 0.3054 (19) | 0.339 (4) | 0.102 (14)* | |
H18 | 0.812 (8) | 0.307 (3) | 0.430 (6) | 0.27 (4)* | |
H20 | 0.603 (4) | 0.2469 (18) | 0.115 (4) | 0.110 (13)* | |
H21 | 0.615 (4) | 0.1906 (16) | 0.113 (3) | 0.079 (12)* | |
H23 | 0.866 (4) | 0.2227 (14) | 0.174 (3) | 0.080 (10)* | |
H22 | 0.997 (3) | 0.2394 (13) | 0.157 (3) | 0.064 (9)* | |
H25 | 0.414 (3) | 0.1274 (12) | 0.027 (3) | 0.056 (8)* | |
H24 | 0.515 (3) | 0.1051 (14) | −0.038 (3) | 0.083 (10)* | |
N1 | 0.19590 (15) | 0.51852 (6) | 0.94600 (14) | 0.0286 (3) | |
N2 | 0.04471 (16) | 0.46506 (7) | 0.74881 (14) | 0.0300 (3) | |
N3 | 0.21798 (17) | 0.34646 (7) | 0.80844 (16) | 0.0274 (3) | |
O1 | 0.34246 (15) | 0.40355 (6) | 1.01718 (12) | 0.0363 (3) | |
O2 | 0.47864 (15) | 0.32287 (6) | 1.08694 (13) | 0.0412 (3) | |
O3 | 0.13927 (15) | 0.26540 (6) | 1.02745 (15) | 0.0435 (3) | |
O4 | 0.23005 (16) | 0.16948 (6) | 1.02283 (14) | 0.0441 (3) | |
O5 | 0.40526 (18) | 0.46956 (8) | 0.74360 (17) | 0.0463 (4) | |
O6 | 0.6063 (3) | 0.39998 (8) | 0.28706 (18) | 0.0540 (4) | |
O7 | 0.4866 (2) | 0.10876 (8) | 0.03831 (18) | 0.0480 (4) | |
O8 | 0.6535 (3) | 0.21492 (12) | 0.1238 (3) | 0.0993 (10) | |
O9 | 0.8536 (4) | 0.33075 (12) | 0.3771 (3) | 0.1023 (10) | |
O10 | 0.9440 (2) | 0.23383 (8) | 0.21627 (17) | 0.0490 (4) | |
H12 | 0.217 (2) | 0.3420 (9) | 0.722 (2) | 0.038 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0328 (9) | 0.0345 (10) | 0.0386 (10) | −0.0022 (8) | 0.0016 (8) | −0.0040 (8) |
C2 | 0.0440 (11) | 0.0414 (12) | 0.0418 (11) | −0.0129 (9) | 0.0076 (9) | −0.0143 (9) |
C3 | 0.0566 (13) | 0.0277 (10) | 0.0518 (12) | −0.0032 (9) | 0.0156 (10) | −0.0124 (9) |
C4 | 0.0461 (11) | 0.0278 (10) | 0.0461 (11) | 0.0079 (9) | 0.0108 (9) | −0.0021 (9) |
C5 | 0.0332 (9) | 0.0243 (8) | 0.0323 (9) | 0.0015 (7) | 0.0090 (7) | 0.0018 (7) |
C6 | 0.0313 (9) | 0.0282 (9) | 0.0316 (9) | 0.0033 (7) | 0.0044 (7) | 0.0040 (7) |
C7 | 0.0487 (12) | 0.0405 (12) | 0.0507 (12) | 0.0169 (10) | −0.0039 (10) | 0.0012 (10) |
C8 | 0.0456 (12) | 0.0581 (15) | 0.0545 (13) | 0.0133 (11) | −0.0157 (10) | 0.0035 (11) |
C9 | 0.0458 (11) | 0.0493 (13) | 0.0446 (12) | −0.0004 (10) | −0.0128 (9) | −0.0019 (10) |
C10 | 0.0435 (11) | 0.0325 (11) | 0.0402 (11) | 0.0001 (8) | −0.0075 (8) | −0.0020 (8) |
C11 | 0.0303 (9) | 0.0273 (9) | 0.0327 (9) | −0.0017 (7) | 0.0003 (7) | 0.0038 (7) |
C12 | 0.0277 (8) | 0.0240 (8) | 0.0298 (9) | 0.0009 (7) | 0.0037 (7) | 0.0031 (7) |
C13 | 0.0350 (9) | 0.0232 (9) | 0.0308 (9) | 0.0049 (7) | 0.0037 (7) | −0.0001 (7) |
C14 | 0.0333 (9) | 0.0268 (9) | 0.0298 (9) | −0.0008 (7) | −0.0004 (7) | 0.0014 (7) |
Cu1 | 0.03180 (13) | 0.02038 (12) | 0.02817 (13) | 0.00241 (8) | −0.00305 (8) | −0.00112 (8) |
N1 | 0.0304 (7) | 0.0246 (7) | 0.0309 (7) | −0.0006 (6) | 0.0031 (6) | −0.0019 (6) |
N2 | 0.0321 (7) | 0.0254 (7) | 0.0321 (8) | 0.0015 (6) | −0.0014 (6) | 0.0008 (6) |
N3 | 0.0314 (8) | 0.0232 (7) | 0.0274 (8) | −0.0005 (6) | −0.0008 (6) | 0.0011 (6) |
O1 | 0.0479 (7) | 0.0271 (7) | 0.0326 (7) | 0.0054 (6) | −0.0092 (5) | −0.0036 (5) |
O2 | 0.0473 (8) | 0.0348 (7) | 0.0399 (7) | 0.0063 (6) | −0.0126 (6) | 0.0029 (6) |
O3 | 0.0456 (8) | 0.0333 (7) | 0.0535 (9) | 0.0095 (6) | 0.0216 (6) | 0.0077 (6) |
O4 | 0.0578 (8) | 0.0251 (7) | 0.0509 (8) | 0.0023 (6) | 0.0166 (7) | 0.0092 (6) |
O5 | 0.0572 (9) | 0.0372 (9) | 0.0460 (9) | −0.0058 (7) | 0.0163 (7) | −0.0036 (7) |
O6 | 0.0726 (12) | 0.0465 (10) | 0.0428 (9) | −0.0149 (9) | 0.0021 (8) | −0.0077 (8) |
O7 | 0.0501 (9) | 0.0436 (9) | 0.0510 (10) | 0.0066 (7) | 0.0092 (8) | 0.0097 (7) |
O8 | 0.0589 (12) | 0.0478 (12) | 0.185 (3) | 0.0065 (11) | −0.0480 (15) | −0.0081 (15) |
O9 | 0.170 (3) | 0.0701 (15) | 0.0654 (14) | 0.0437 (17) | −0.0049 (15) | −0.0084 (12) |
O10 | 0.0436 (9) | 0.0599 (10) | 0.0441 (9) | 0.0039 (7) | 0.0072 (8) | 0.0105 (7) |
Geometric parameters (Å, º) top
C1—N1 | 1.337 (2) | C12—H13 | 0.961 (19) |
C1—C2 | 1.381 (3) | C13—C14 | 1.520 (2) |
C1—H1 | 0.88 (2) | C13—H14 | 0.92 (2) |
C2—C3 | 1.375 (3) | C13—H15 | 0.92 (2) |
C2—H2 | 0.89 (2) | C14—O3 | 1.242 (2) |
C3—C4 | 1.374 (3) | C14—O4 | 1.259 (2) |
C3—H3 | 0.91 (2) | Cu1—O1 | 1.9484 (12) |
C4—C5 | 1.380 (3) | Cu1—N3 | 1.9722 (15) |
C4—H4 | 0.87 (2) | Cu1—N1 | 1.9856 (14) |
C5—N1 | 1.350 (2) | Cu1—N2 | 2.0130 (14) |
C5—C6 | 1.481 (2) | Cu1—O5 | 2.2840 (15) |
C6—N2 | 1.348 (2) | N3—H11 | 0.81 (2) |
C6—C7 | 1.386 (3) | N3—H12 | 0.87 (2) |
C7—C8 | 1.380 (3) | O5—H9 | 0.80 (3) |
C7—H5 | 0.92 (2) | O5—H10 | 0.79 (3) |
C8—C9 | 1.368 (3) | O6—H16 | 0.67 (3) |
C8—H6 | 0.91 (3) | O6—H17 | 0.87 (5) |
C9—C10 | 1.373 (3) | O7—H25 | 0.77 (3) |
C9—H7 | 0.96 (2) | O7—H24 | 0.82 (3) |
C10—N2 | 1.339 (2) | O8—H20 | 0.82 (4) |
C10—H8 | 0.94 (2) | O8—H21 | 0.63 (3) |
C11—O2 | 1.237 (2) | O9—H19 | 0.73 (4) |
C11—O1 | 1.274 (2) | O9—H18 | 0.846 (10) |
C11—C12 | 1.530 (2) | O10—H23 | 0.84 (3) |
C12—N3 | 1.478 (2) | O10—H22 | 0.79 (3) |
C12—C13 | 1.521 (2) | | |
| | | |
N1—C1—C2 | 121.62 (19) | C14—C13—H14 | 107.1 (13) |
N1—C1—H1 | 115.0 (13) | C12—C13—H14 | 110.9 (13) |
C2—C1—H1 | 123.4 (13) | C14—C13—H15 | 107.8 (13) |
C3—C2—C1 | 118.88 (19) | C12—C13—H15 | 110.2 (13) |
C3—C2—H2 | 123.1 (15) | H14—C13—H15 | 106.5 (18) |
C1—C2—H2 | 118.0 (15) | O3—C14—O4 | 124.64 (17) |
C4—C3—C2 | 119.72 (19) | O3—C14—C13 | 118.19 (15) |
C4—C3—H3 | 121.6 (15) | O4—C14—C13 | 117.17 (15) |
C2—C3—H3 | 118.7 (15) | O1—Cu1—N3 | 83.98 (6) |
C3—C4—C5 | 119.1 (2) | O1—Cu1—N1 | 93.66 (5) |
C3—C4—H4 | 121.5 (15) | N3—Cu1—N1 | 171.65 (6) |
C5—C4—H4 | 119.4 (15) | O1—Cu1—N2 | 164.41 (6) |
N1—C5—C4 | 121.17 (17) | N3—Cu1—N2 | 98.88 (6) |
N1—C5—C6 | 114.44 (15) | N1—Cu1—N2 | 81.30 (6) |
C4—C5—C6 | 124.39 (17) | O1—Cu1—O5 | 96.40 (6) |
N2—C6—C7 | 121.10 (17) | N3—Cu1—O5 | 98.01 (7) |
N2—C6—C5 | 114.80 (15) | N1—Cu1—O5 | 90.21 (6) |
C7—C6—C5 | 124.10 (17) | N2—Cu1—O5 | 98.36 (6) |
C8—C7—C6 | 118.9 (2) | C1—N1—C5 | 119.53 (15) |
C8—C7—H5 | 121.7 (14) | C1—N1—Cu1 | 125.23 (13) |
C6—C7—H5 | 119.4 (15) | C5—N1—Cu1 | 115.22 (11) |
C9—C8—C7 | 119.91 (19) | C10—N2—C6 | 119.00 (15) |
C9—C8—H6 | 122.6 (18) | C10—N2—Cu1 | 126.78 (12) |
C7—C8—H6 | 117.4 (18) | C6—N2—Cu1 | 114.18 (11) |
C8—C9—C10 | 118.6 (2) | C12—N3—Cu1 | 108.31 (10) |
C8—C9—H7 | 122.4 (14) | C12—N3—H11 | 107.0 (14) |
C10—C9—H7 | 119.0 (14) | Cu1—N3—H11 | 109.2 (14) |
N2—C10—C9 | 122.55 (19) | C12—N3—H12 | 109.6 (14) |
N2—C10—H8 | 116.3 (13) | Cu1—N3—H12 | 113.6 (14) |
C9—C10—H8 | 121.1 (13) | H11—N3—H12 | 109 (2) |
O2—C11—O1 | 123.55 (16) | C11—O1—Cu1 | 115.18 (11) |
O2—C11—C12 | 119.94 (15) | Cu1—O5—H9 | 113.4 (19) |
O1—C11—C12 | 116.41 (14) | Cu1—O5—H10 | 122.8 (18) |
N3—C12—C13 | 113.23 (14) | H9—O5—H10 | 110 (3) |
N3—C12—C11 | 108.74 (13) | H16—O6—H17 | 102 (4) |
C13—C12—C11 | 113.60 (14) | H25—O7—H24 | 103 (3) |
N3—C12—H13 | 108.9 (10) | H20—O8—H21 | 112 (4) |
C13—C12—H13 | 108.2 (11) | H19—O9—H18 | 94 (5) |
C11—C12—H13 | 103.7 (11) | H23—O10—H22 | 100 (3) |
C14—C13—C12 | 114.03 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H12···O4i | 0.87 (2) | 2.02 (2) | 2.890 (2) | 176.1 (19) |
O7—H24···O6i | 0.82 (3) | 1.98 (4) | 2.799 (3) | 173 (3) |
O7—H25···O4ii | 0.77 (3) | 1.89 (3) | 2.652 (2) | 173 (3) |
O10—H23···O8 | 0.84 (3) | 1.96 (3) | 2.762 (3) | 159 (3) |
O10—H22···O3iii | 0.79 (3) | 1.95 (3) | 2.738 (2) | 170 (3) |
O8—H21···O7 | 0.63 (3) | 2.21 (3) | 2.836 (3) | 170 (4) |
O8—H20···O2ii | 0.82 (4) | 1.99 (4) | 2.814 (3) | 178 (4) |
O9—H19···O10 | 0.73 (4) | 2.05 (4) | 2.779 (3) | 172 (4) |
O9—H18···O8iv | 0.85 (1) | 2.51 (4) | 3.287 (5) | 153 (7) |
O6—H17···O9 | 0.87 (5) | 1.93 (5) | 2.789 (4) | 166 (5) |
O6—H16···O2ii | 0.67 (3) | 2.14 (3) | 2.799 (2) | 170 (3) |
N3—H11···O10v | 0.81 (2) | 2.52 (2) | 3.111 (2) | 131.0 (17) |
N3—H11···O3 | 0.81 (2) | 2.35 (2) | 2.917 (2) | 127.4 (17) |
O5—H10···O7iv | 0.79 (3) | 2.01 (3) | 2.784 (2) | 166 (2) |
O5—H9···O6vi | 0.80 (3) | 2.02 (3) | 2.815 (3) | 177 (3) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y, z−1; (iii) x+1, y, z−1; (iv) x, −y+1/2, z+1/2; (v) x−1, −y+1/2, z+1/2; (vi) −x+1, −y+1, −z+1. |