In the title complex, [Cu(C
4H
4O
5)(C
10H
8N
2)(H
2O)], the chiral
L-malate group, which acts as a tridentate ligand, the bidentate 2,2′-bipyridine ligand and the water molecule provide an octahedral coordination of the Cu
II atom with strong Jahn–Teller distortion. Intermolecular O—H
O hydrogen bonds stabilize the crystal packing.
Supporting information
CCDC reference: 283790
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.028
- wR factor = 0.070
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O3 .. 5.76 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O5 .. 8.52 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - N2 .. 5.28 su
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 3102
Count of symmetry unique reflns 1786
Completeness (_total/calc) 173.68%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1316
Fraction of Friedel pairs measured 0.737
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Aqua(2,2'-bipyridine-
κ2N,
N')(
L-malato-
κ3O,
O',
O'')copper(II)
top
Crystal data top
[Cu(C4H4O5)(C10H8N2)(H2O)] | F(000) = 378 |
Mr = 369.81 | Dx = 1.714 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 5265 reflections |
a = 10.4874 (6) Å | θ = 3.7–27.5° |
b = 6.5998 (3) Å | µ = 1.56 mm−1 |
c = 10.7986 (4) Å | T = 293 K |
β = 106.570 (2)° | Prism, blue |
V = 716.38 (6) Å3 | 0.30 × 0.23 × 0.09 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3102 independent reflections |
Radiation source: fine-focus sealed tube | 2966 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.043 |
ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→13 |
Tmin = 0.657, Tmax = 0.869 | k = −8→8 |
6910 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.032P)2 + 0.1622P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.070 | (Δ/σ)max = 0.001 |
S = 1.11 | Δρmax = 0.24 e Å−3 |
3102 reflections | Δρmin = −0.33 e Å−3 |
225 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
4 restraints | Extinction coefficient: 0.0326 (18) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1318 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.028 (11) |
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 | x | y | z | Uiso*/Ueq | |
Cu | 0.19669 (2) | 0.25000 (5) | 0.18940 (2) | 0.02741 (10) | |
O1 | 0.01430 (14) | 0.2499 (5) | 0.08411 (14) | 0.0332 (3) | |
O2 | −0.18387 (18) | 0.3331 (3) | 0.10466 (19) | 0.0391 (4) | |
O3 | 0.11771 (17) | 0.1672 (3) | 0.33077 (17) | 0.0264 (3) | |
O4 | 0.04892 (19) | 0.8028 (3) | 0.35711 (18) | 0.0321 (4) | |
O5 | 0.15784 (19) | 0.5808 (3) | 0.27066 (19) | 0.0356 (4) | |
O6 | 0.2615 (2) | −0.1032 (3) | 0.16271 (19) | 0.0385 (4) | |
N1 | 0.38459 (18) | 0.2805 (3) | 0.29485 (19) | 0.0265 (4) | |
N2 | 0.27600 (19) | 0.3108 (3) | 0.04689 (19) | 0.0270 (4) | |
C1 | 0.4294 (2) | 0.2690 (5) | 0.4234 (2) | 0.0347 (5) | |
H1 | 0.3684 | 0.2525 | 0.4704 | 0.042* | |
C2 | 0.5633 (3) | 0.2808 (5) | 0.4891 (3) | 0.0410 (7) | |
H2 | 0.5924 | 0.2707 | 0.5787 | 0.049* | |
C3 | 0.6526 (3) | 0.3079 (5) | 0.4181 (3) | 0.0439 (7) | |
H3 | 0.7432 | 0.3163 | 0.4599 | 0.053* | |
C4 | 0.6078 (3) | 0.3224 (5) | 0.2856 (3) | 0.0382 (6) | |
H4 | 0.6673 | 0.3416 | 0.2372 | 0.046* | |
C5 | 0.4715 (2) | 0.3076 (3) | 0.2253 (2) | 0.0270 (5) | |
C6 | 0.4102 (2) | 0.3187 (4) | 0.0837 (2) | 0.0259 (5) | |
C7 | 0.4816 (3) | 0.3319 (4) | −0.0060 (3) | 0.0337 (5) | |
H7 | 0.5741 | 0.3354 | 0.0205 | 0.040* | |
C8 | 0.4124 (3) | 0.3397 (4) | −0.1359 (3) | 0.0372 (6) | |
H8 | 0.4580 | 0.3479 | −0.1980 | 0.045* | |
C9 | 0.2752 (3) | 0.3352 (5) | −0.1724 (2) | 0.0361 (6) | |
H9 | 0.2274 | 0.3424 | −0.2593 | 0.043* | |
C10 | 0.2095 (3) | 0.3199 (4) | −0.0785 (2) | 0.0323 (5) | |
H10 | 0.1170 | 0.3158 | −0.1032 | 0.039* | |
C11 | −0.0663 (2) | 0.2827 (4) | 0.1498 (2) | 0.0265 (5) | |
C12 | −0.01219 (19) | 0.2583 (5) | 0.29726 (19) | 0.0238 (4) | |
C13 | −0.0080 (2) | 0.4594 (4) | 0.3662 (2) | 0.0273 (5) | |
H13A | 0.0279 | 0.4363 | 0.4583 | 0.033* | |
H13B | −0.0985 | 0.5077 | 0.3510 | 0.033* | |
C14 | 0.0736 (2) | 0.6267 (4) | 0.3269 (2) | 0.0228 (5) | |
H31 | 0.122 (4) | 0.050 (6) | 0.336 (3) | 0.055 (11)* | |
H12 | −0.0722 | 0.1667 | 0.3261 | 0.029* | |
H61 | 0.229 (4) | −0.200 (4) | 0.196 (3) | 0.073 (14)* | |
H62 | 0.240 (3) | −0.116 (5) | 0.081 (2) | 0.052 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.01775 (12) | 0.03661 (16) | 0.02827 (13) | −0.00101 (14) | 0.00719 (8) | 0.00198 (16) |
O1 | 0.0221 (7) | 0.0489 (9) | 0.0284 (7) | −0.0003 (11) | 0.0070 (5) | −0.0035 (12) |
O2 | 0.0223 (8) | 0.0532 (11) | 0.0417 (10) | 0.0053 (8) | 0.0089 (7) | 0.0033 (9) |
O3 | 0.0253 (8) | 0.0202 (8) | 0.0347 (9) | 0.0008 (6) | 0.0099 (7) | 0.0024 (7) |
O4 | 0.0409 (10) | 0.0189 (9) | 0.0395 (9) | −0.0030 (6) | 0.0163 (7) | −0.0051 (7) |
O5 | 0.0401 (10) | 0.0247 (9) | 0.0510 (11) | −0.0013 (7) | 0.0276 (9) | 0.0019 (8) |
O6 | 0.0475 (12) | 0.0337 (10) | 0.0371 (10) | −0.0116 (9) | 0.0166 (9) | −0.0031 (9) |
N1 | 0.0228 (8) | 0.0236 (12) | 0.0324 (9) | −0.0005 (8) | 0.0069 (7) | 0.0003 (9) |
N2 | 0.0216 (9) | 0.0263 (10) | 0.0331 (9) | −0.0006 (7) | 0.0079 (7) | 0.0019 (8) |
C1 | 0.0332 (11) | 0.0356 (15) | 0.0344 (11) | −0.0019 (13) | 0.0082 (9) | 0.0015 (14) |
C2 | 0.0367 (13) | 0.043 (2) | 0.0350 (11) | −0.0015 (12) | −0.0023 (9) | 0.0024 (13) |
C3 | 0.0246 (12) | 0.0504 (18) | 0.0494 (15) | −0.0025 (11) | −0.0009 (10) | 0.0011 (13) |
C4 | 0.0233 (11) | 0.0437 (15) | 0.0467 (14) | −0.0031 (10) | 0.0087 (10) | 0.0000 (13) |
C5 | 0.0218 (10) | 0.0240 (12) | 0.0349 (11) | −0.0011 (8) | 0.0076 (8) | −0.0006 (9) |
C6 | 0.0231 (10) | 0.0204 (10) | 0.0344 (11) | −0.0007 (8) | 0.0086 (9) | 0.0010 (9) |
C7 | 0.0278 (12) | 0.0329 (12) | 0.0446 (14) | −0.0013 (10) | 0.0171 (10) | 0.0012 (11) |
C8 | 0.0446 (15) | 0.0309 (13) | 0.0436 (14) | −0.0009 (12) | 0.0248 (12) | 0.0018 (12) |
C9 | 0.0421 (14) | 0.0354 (13) | 0.0300 (12) | −0.0001 (11) | 0.0089 (11) | 0.0023 (11) |
C10 | 0.0272 (11) | 0.0337 (12) | 0.0343 (11) | 0.0012 (9) | 0.0059 (9) | 0.0029 (10) |
C11 | 0.0214 (9) | 0.0230 (14) | 0.0352 (10) | −0.0024 (8) | 0.0080 (8) | −0.0022 (10) |
C12 | 0.0226 (8) | 0.0191 (9) | 0.0330 (10) | −0.0020 (11) | 0.0131 (7) | 0.0040 (13) |
C13 | 0.0327 (12) | 0.0220 (11) | 0.0325 (11) | 0.0006 (9) | 0.0177 (10) | 0.0020 (10) |
C14 | 0.0239 (11) | 0.0198 (11) | 0.0230 (10) | −0.0017 (8) | 0.0038 (8) | 0.0012 (9) |
Geometric parameters (Å, º) top
Cu—O1 | 1.9264 (14) | C2—H2 | 0.9300 |
Cu—O3 | 2.0090 (18) | C3—C4 | 1.376 (4) |
Cu—O5 | 2.4301 (18) | C3—H3 | 0.9300 |
Cu—O6 | 2.468 (2) | C4—C5 | 1.396 (3) |
Cu—N1 | 1.9850 (19) | C4—H4 | 0.9300 |
Cu—N2 | 1.988 (2) | C5—C6 | 1.481 (3) |
O1—C11 | 1.267 (3) | C6—C7 | 1.387 (3) |
O2—C11 | 1.235 (3) | C7—C8 | 1.384 (4) |
O3—C12 | 1.438 (3) | C7—H7 | 0.9300 |
O3—H31 | 0.77 (4) | C8—C9 | 1.380 (4) |
O4—C14 | 1.254 (3) | C8—H8 | 0.9300 |
O5—C14 | 1.244 (3) | C9—C10 | 1.383 (4) |
O6—H61 | 0.85 (3) | C9—H9 | 0.9300 |
O6—H62 | 0.85 (2) | C10—H10 | 0.9300 |
N1—C1 | 1.335 (3) | C11—C12 | 1.539 (3) |
N1—C5 | 1.348 (3) | C12—C13 | 1.516 (4) |
N2—C10 | 1.336 (3) | C12—H12 | 0.9900 |
N2—C6 | 1.349 (3) | C13—C14 | 1.529 (3) |
C1—C2 | 1.383 (3) | C13—H13A | 0.9700 |
C1—H1 | 0.9300 | C13—H13B | 0.9700 |
C2—C3 | 1.380 (4) | | |
| | | |
O1—Cu—O3 | 83.87 (7) | C5—C4—H4 | 120.6 |
O1—Cu—O5 | 88.45 (9) | N1—C5—C4 | 121.0 (2) |
O1—Cu—O6 | 100.98 (9) | N1—C5—C6 | 114.7 (2) |
O1—Cu—N1 | 174.12 (13) | C4—C5—C6 | 124.3 (2) |
O1—Cu—N2 | 96.17 (7) | N2—C6—C7 | 121.5 (2) |
O3—Cu—O5 | 79.74 (7) | N2—C6—C5 | 114.3 (2) |
O3—Cu—O6 | 91.05 (7) | C7—C6—C5 | 124.2 (2) |
O3—Cu—N1 | 98.55 (8) | C8—C7—C6 | 118.6 (2) |
O3—Cu—N2 | 175.88 (9) | C8—C7—H7 | 120.7 |
O5—Cu—O6 | 166.12 (7) | C6—C7—H7 | 120.7 |
O5—Cu—N1 | 86.73 (8) | C9—C8—C7 | 119.5 (2) |
O5—Cu—N2 | 104.38 (7) | C9—C8—H8 | 120.3 |
O6—Cu—N1 | 84.38 (8) | C7—C8—H8 | 120.3 |
O6—Cu—N2 | 84.88 (7) | C8—C9—C10 | 119.3 (2) |
N1—Cu—N2 | 81.81 (8) | C8—C9—H9 | 120.4 |
C11—O1—Cu | 112.22 (13) | C10—C9—H9 | 120.4 |
C12—O3—Cu | 105.16 (13) | N2—C10—C9 | 121.4 (2) |
C12—O3—H31 | 117 (3) | N2—C10—H10 | 119.3 |
Cu—O3—H31 | 108 (3) | C9—C10—H10 | 119.3 |
C14—O5—Cu | 127.64 (15) | O2—C11—O1 | 125.1 (2) |
H61—O6—H62 | 110 (3) | O2—C11—C12 | 117.9 (2) |
C1—N1—C5 | 119.6 (2) | O1—C11—C12 | 116.97 (18) |
C1—N1—Cu | 126.04 (16) | O3—C12—C13 | 110.45 (19) |
C5—N1—Cu | 114.33 (16) | O3—C12—C11 | 110.31 (17) |
C10—N2—C6 | 119.7 (2) | C13—C12—C11 | 111.6 (2) |
C10—N2—Cu | 125.52 (17) | O3—C12—H12 | 108.00 |
C6—N2—Cu | 114.26 (16) | C13—C12—H12 | 108.00 |
N1—C1—C2 | 122.4 (2) | C11—C12—H12 | 108.00 |
N1—C1—H1 | 118.8 | C12—C13—C14 | 115.87 (19) |
C2—C1—H1 | 118.8 | C12—C13—H13A | 108.3 |
C3—C2—C1 | 118.2 (2) | C14—C13—H13A | 108.3 |
C3—C2—H2 | 120.9 | C12—C13—H13B | 108.3 |
C1—C2—H2 | 120.9 | C14—C13—H13B | 108.3 |
C4—C3—C2 | 120.2 (2) | H13A—C13—H13B | 107.4 |
C4—C3—H3 | 119.9 | O5—C14—O4 | 125.5 (2) |
C2—C3—H3 | 119.9 | O5—C14—C13 | 119.4 (2) |
C3—C4—C5 | 118.7 (3) | O4—C14—C13 | 115.11 (19) |
C3—C4—H4 | 120.6 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···O4i | 0.78 (4) | 1.84 (4) | 2.551 (3) | 151 (4) |
O6—H61···O5i | 0.85 (3) | 1.90 (3) | 2.759 (3) | 179 (4) |
O6—H62···O2ii | 0.85 (2) | 1.95 (2) | 2.799 (3) | 175 (3) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1/2, −z. |