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metal-organic compounds
Di-2-pyridyl ketone undergoes hydrolysis when reacted with copper(II) acetate to form the title compound, [Cu(C11H10N2O2)2](C2H3O2)2·4H2O. The crystal structure consists of octahedral cations that are linked to the anions and to the uncoordinated water molecules, giving rise to a three-dimensional network structure. This C-centered monoclinic modification is less compact than the primitive monoclinic modification reported by Reinoso et al. [(2003). Acta Cryst. E59, m548–m550]. The Cu atom is located at a center of inversion.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033987/dn6187sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033987/dn6187Isup2.hkl |
CCDC reference: 263528
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.119
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1W2 ... ? PLAT420_ALERT_2_B D-H Without Acceptor O2W - H2W2 ... ?
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 7.39 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C12 PLAT415_ALERT_2_C Short Inter D-H..H-X H1O .. H4 .. 2.11 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Cu(C11H10N2O2)2](C2H3O2)2·4H2O | F(000) = 1372 |
Mr = 658.11 | Dx = 1.366 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 9126 reflections |
a = 23.557 (2) Å | θ = 2.5–27.0° |
b = 8.5744 (6) Å | µ = 0.75 mm−1 |
c = 15.848 (1) Å | T = 293 K |
β = 91.983 (1)° | Prism, purple |
V = 3199.2 (4) Å3 | 0.36 × 0.34 × 0.28 mm |
Z = 4 |
Data collection top
Rigaku Mercury CCD diffractometer | 3587 independent reflections |
Radiation source: rotating-anode generator | 3064 reflections with I > 2s(I) |
Graphite Monochromator monochromator | Rint = 0.017 |
w scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002) | h = −30→29 |
Tmin = 0.772, Tmax = 0.811 | k = −10→7 |
9295 measured reflections | l = −19→20 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0725P)2 + 1.3743P] where P = (Fo2 + 2Fc2)/3 |
3587 reflections | (Δ/σ)max = 0.001 |
198 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.2500 | 0.7500 | 0.5000 | 0.0350 (1) | |
O1 | 0.3031 (1) | 0.7385 (1) | 0.3740 (1) | 0.0401 (3) | |
O2 | 0.3104 (1) | 0.5265 (2) | 0.2831 (1) | 0.0509 (4) | |
O3 | 0.4117 (1) | 0.7548 (2) | 0.3886 (2) | 0.0714 (6) | |
O4 | 0.4208 (1) | 0.5351 (2) | 0.3183 (1) | 0.0731 (5) | |
O1w | 0.4533 (1) | 1.0333 (2) | 0.4485 (1) | 0.0828 (6) | |
O2w | 0.4696 (1) | 1.2386 (2) | 0.3210 (1) | 0.0912 (8) | |
N1 | 0.1975 (1) | 0.6555 (2) | 0.4103 (1) | 0.0399 (4) | |
N2 | 0.2900 (1) | 0.5442 (2) | 0.5072 (1) | 0.0378 (3) | |
C1 | 0.1405 (1) | 0.6602 (3) | 0.4097 (1) | 0.0510 (5) | |
C2 | 0.1080 (1) | 0.5935 (3) | 0.3456 (2) | 0.0627 (6) | |
C3 | 0.1343 (1) | 0.5209 (3) | 0.2806 (2) | 0.0617 (6) | |
C4 | 0.1929 (1) | 0.5140 (3) | 0.2810 (1) | 0.0496 (5) | |
C5 | 0.2231 (1) | 0.5829 (2) | 0.3467 (1) | 0.0387 (4) | |
C6 | 0.2875 (1) | 0.5824 (2) | 0.3561 (1) | 0.0379 (4) | |
C7 | 0.3040 (1) | 0.4816 (2) | 0.4331 (1) | 0.0369 (4) | |
C8 | 0.3307 (1) | 0.3385 (2) | 0.4295 (2) | 0.0515 (5) | |
C9 | 0.3439 (1) | 0.2610 (3) | 0.5041 (2) | 0.0656 (7) | |
C10 | 0.3295 (1) | 0.3262 (3) | 0.5792 (2) | 0.0658 (7) | |
C11 | 0.3025 (1) | 0.4677 (3) | 0.5790 (1) | 0.0504 (5) | |
C12 | 0.4408 (1) | 0.6456 (3) | 0.3601 (2) | 0.0647 (6) | |
C13 | 0.5040 (1) | 0.6478 (5) | 0.3797 (3) | 0.122 (2) | |
H1o | 0.3230 | 0.8018 | 0.3501 | 0.048* | |
H2o | 0.3451 | 0.5261 | 0.2884 | 0.061* | |
H1w1 | 0.4387 | 0.9503 | 0.4353 | 0.099* | |
H1w2 | 0.4460 | 1.0592 | 0.4964 | 0.099* | |
H2w1 | 0.4480 | 1.3097 | 0.3055 | 0.109* | |
H2w2 | 0.4964 | 1.2805 | 0.3466 | 0.109* | |
H1 | 0.1226 | 0.7096 | 0.4537 | 0.061* | |
H2 | 0.0686 | 0.5976 | 0.3464 | 0.075* | |
H3 | 0.1128 | 0.4766 | 0.2365 | 0.074* | |
H4 | 0.2115 | 0.4639 | 0.2378 | 0.060* | |
H8 | 0.3396 | 0.2950 | 0.3779 | 0.062* | |
H9 | 0.3625 | 0.1653 | 0.5033 | 0.079* | |
H10 | 0.3379 | 0.2750 | 0.6298 | 0.079* | |
H11 | 0.2927 | 0.5117 | 0.6301 | 0.061* | |
H13a | 0.5204 | 0.5508 | 0.3625 | 0.183* | |
H13b | 0.5108 | 0.6619 | 0.4393 | 0.183* | |
H13c | 0.5211 | 0.7321 | 0.3497 | 0.183* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0398 (2) | 0.0393 (2) | 0.0258 (2) | 0.0078 (1) | −0.0004 (1) | −0.0038 (1) |
O1 | 0.0468 (8) | 0.0398 (7) | 0.0337 (7) | −0.0021 (5) | 0.0028 (6) | 0.0048 (5) |
O2 | 0.0502 (8) | 0.0726 (10) | 0.0303 (7) | 0.0053 (7) | 0.0070 (6) | −0.0119 (6) |
O3 | 0.0493 (10) | 0.0669 (12) | 0.0980 (16) | −0.0015 (7) | 0.0024 (10) | −0.0202 (9) |
O4 | 0.0517 (9) | 0.0812 (13) | 0.0872 (13) | 0.0029 (8) | 0.0117 (9) | −0.0212 (10) |
O1w | 0.0945 (14) | 0.0654 (12) | 0.0882 (14) | 0.0032 (10) | −0.0007 (11) | −0.0099 (10) |
O2w | 0.0921 (18) | 0.0816 (17) | 0.101 (2) | 0.0132 (10) | 0.0156 (15) | 0.0048 (11) |
N1 | 0.0398 (8) | 0.0463 (9) | 0.0335 (8) | 0.0062 (6) | −0.0009 (6) | −0.0043 (6) |
N2 | 0.0424 (8) | 0.0410 (8) | 0.0299 (7) | 0.0066 (6) | 0.0021 (6) | 0.0016 (6) |
C1 | 0.0423 (10) | 0.0614 (13) | 0.0490 (12) | 0.0101 (9) | 0.0000 (8) | −0.0061 (10) |
C2 | 0.0412 (11) | 0.0831 (17) | 0.0630 (14) | 0.0045 (11) | −0.0093 (10) | −0.0070 (13) |
C3 | 0.0569 (13) | 0.0753 (16) | 0.0515 (13) | −0.0014 (11) | −0.0172 (10) | −0.0130 (11) |
C4 | 0.0551 (12) | 0.0583 (13) | 0.0352 (10) | 0.0018 (9) | −0.0038 (8) | −0.0091 (9) |
C5 | 0.0421 (9) | 0.0440 (10) | 0.0298 (8) | 0.0043 (8) | −0.0004 (7) | −0.0007 (7) |
C6 | 0.0417 (9) | 0.0452 (10) | 0.0269 (8) | 0.0042 (7) | 0.0035 (7) | −0.0044 (7) |
C7 | 0.0371 (9) | 0.0385 (9) | 0.0350 (9) | 0.0017 (7) | 0.0033 (7) | −0.0020 (7) |
C8 | 0.0551 (12) | 0.0434 (11) | 0.0564 (13) | 0.0107 (9) | 0.0098 (10) | −0.0040 (9) |
C9 | 0.0699 (17) | 0.0475 (13) | 0.080 (2) | 0.0200 (11) | 0.0061 (14) | 0.0119 (11) |
C10 | 0.0732 (16) | 0.0640 (16) | 0.0601 (15) | 0.0182 (12) | 0.0022 (12) | 0.0261 (12) |
C11 | 0.0571 (12) | 0.0580 (13) | 0.0364 (10) | 0.0080 (10) | 0.0037 (8) | 0.0100 (9) |
C12 | 0.0468 (12) | 0.0762 (17) | 0.0717 (16) | −0.0011 (12) | 0.0095 (11) | −0.0063 (13) |
C13 | 0.0510 (16) | 0.137 (4) | 0.177 (4) | 0.0064 (19) | −0.002 (2) | −0.062 (3) |
Geometric parameters (Å, º) top
Cu1—O1 | 2.394 (1) | C8—C9 | 1.383 (4) |
Cu1—O1i | 2.394 (1) | C9—C10 | 1.368 (4) |
Cu1—N1 | 2.021 (2) | C10—C11 | 1.369 (3) |
Cu1—N1i | 2.021 (2) | C12—C13 | 1.512 (4) |
Cu1—N2 | 2.002 (2) | O1—H1o | 0.82 |
Cu1—N2i | 2.002 (2) | O2—H2o | 0.82 |
O1—C6 | 1.414 (2) | O1w—H1w1 | 0.82 |
O2—C6 | 1.379 (2) | O1w—H1w2 | 0.82 |
O3—C12 | 1.254 (3) | O2w—H2w1 | 0.83 |
O4—C12 | 1.240 (3) | O2w—H2w2 | 0.82 |
N1—C1 | 1.343 (2) | C1—H1 | 0.93 |
N1—C5 | 1.344 (2) | C2—H2 | 0.93 |
N2—C11 | 1.338 (2) | C3—H3 | 0.93 |
N2—C7 | 1.343 (2) | C4—H4 | 0.93 |
C1—C2 | 1.376 (3) | C8—H8 | 0.93 |
C2—C3 | 1.370 (3) | C9—H9 | 0.93 |
C3—C4 | 1.382 (3) | C10—H10 | 0.93 |
C4—C5 | 1.375 (3) | C11—H11 | 0.93 |
C5—C6 | 1.518 (3) | C13—H13a | 0.96 |
C6—C7 | 1.535 (3) | C13—H13b | 0.96 |
C7—C8 | 1.380 (3) | C13—H13c | 0.96 |
O1—Cu1—O1i | 180 | N2—C7—C6 | 114.0 (2) |
O1—Cu1—N1 | 73.81 (5) | C8—C7—C6 | 124.9 (2) |
O1—Cu1—N1i | 106.19 (6) | C7—C8—C9 | 118.8 (2) |
O1—Cu1—N2 | 75.68 (5) | C10—C9—C8 | 119.4 (2) |
O1—Cu1—N2i | 104.32 (5) | C9—C10—C11 | 119.3 (2) |
O1i—Cu1—N1 | 106.19 (6) | N2—C11—C10 | 121.7 (2) |
O1i—Cu1—N1i | 73.81 (5) | O4—C12—O3 | 124.1 (2) |
O1i—Cu1—N2 | 104.32 (5) | O4—C12—C13 | 118.2 (3) |
O1i—Cu1—N2i | 75.68 (5) | O3—C12—C13 | 117.7 (3) |
N1—Cu1—N1i | 180.0 | C6—O1—H1o | 133.1 |
N1—Cu1—N2 | 87.84 (6) | Cu1—O1—H1o | 133.1 |
N1—Cu1—N2i | 92.16 (6) | C6—O2—H2o | 109.5 |
N1i—Cu1—N2 | 92.16 (6) | H1w1—O1w—H1w2 | 112.2 |
N1i—Cu1—N2i | 87.84 (6) | H2w1—O2w—H2w2 | 106.2 |
N2—Cu1—N2i | 180 | N1—C1—H1 | 119.2 |
C6—O1—Cu1 | 93.9 (1) | C2—C1—H1 | 119.2 |
C1—N1—C5 | 118.9 (2) | C3—C2—H2 | 120.4 |
C1—N1—Cu1 | 125.4 (1) | C1—C2—H2 | 120.4 |
C5—N1—Cu1 | 115.7 (1) | C2—C3—H3 | 120.2 |
C11—N2—C7 | 119.6 (2) | C4—C3—H3 | 120.2 |
C11—N2—Cu1 | 124.8 (1) | C5—C4—H4 | 120.8 |
C7—N2—Cu1 | 115.6 (1) | C3—C4—H4 | 120.8 |
N1—C1—C2 | 121.6 (2) | C7—C8—H8 | 120.6 |
C3—C2—C1 | 119.3 (2) | C9—C8—H8 | 120.6 |
C2—C3—C4 | 119.6 (2) | C10—C9—H9 | 120.3 |
C5—C4—C3 | 118.4 (2) | C8—C9—H9 | 120.3 |
N1—C5—C4 | 122.2 (2) | C9—C10—H10 | 120.3 |
N1—C5—C6 | 113.6 (2) | C11—C10—H10 | 120.3 |
C4—C5—C6 | 124.2 (2) | N2—C11—H11 | 119.2 |
O2—C6—O1 | 113.0 (2) | C10—C11—H11 | 119.2 |
O2—C6—C5 | 109.7 (2) | C12—C13—H13a | 109.5 |
O1—C6—C5 | 105.6 (2) | C12—C13—H13b | 109.5 |
O2—C6—C7 | 112.0 (2) | H13a—C13—H13b | 109.5 |
O1—C6—C7 | 108.4 (1) | C12—C13—H13c | 109.5 |
C5—C6—C7 | 107.7 (2) | H13a—C13—H13c | 109.5 |
N2—C7—C8 | 121.1 (2) | H13b—C13—H13c | 109.5 |
N2—Cu1—O1—C6 | 44.7 (1) | C3—C4—C5—N1 | 0.3 (3) |
N2i—Cu1—O1—C6 | −135.3 (1) | C3—C4—C5—C6 | 179.1 (2) |
N1—Cu1—O1—C6 | −47.2 (1) | Cu1—O1—C6—O2 | 179.6 (1) |
N1i—Cu1—O1—C6 | 132.8 (1) | Cu1—O1—C6—C5 | 59.7 (1) |
N2—Cu1—N1—C1 | 129.4 (2) | Cu1—O1—C6—C7 | −55.6 (1) |
N2i—Cu1—N1—C1 | −50.6 (2) | N1—C5—C6—O2 | −171.3 (2) |
O1—Cu1—N1—C1 | −154.9 (2) | C4—C5—C6—O2 | 9.8 (3) |
O1i—Cu1—N1—C1 | 25.1 (2) | N1—C5—C6—O1 | −49.2 (2) |
N2—Cu1—N1—C5 | −50.6 (1) | C4—C5—C6—O1 | 131.9 (2) |
N2i—Cu1—N1—C5 | 129.4 (1) | N1—C5—C6—C7 | 66.5 (2) |
O1—Cu1—N1—C5 | 25.1 (1) | C4—C5—C6—C7 | −112.4 (2) |
O1i—Cu1—N1—C5 | −154.9 (1) | C11—N2—C7—C8 | 0.7 (3) |
N1—Cu1—N2—C11 | −130.7 (2) | Cu1—N2—C7—C8 | −178.6 (2) |
N1i—Cu1—N2—C11 | 49.3 (2) | C11—N2—C7—C6 | −179.6 (2) |
O1—Cu1—N2—C11 | 155.5 (2) | Cu1—N2—C7—C6 | 1.1 (2) |
O1i—Cu1—N2—C11 | −24.5 (2) | O2—C6—C7—N2 | 170.4 (2) |
N1—Cu1—N2—C7 | 48.6 (1) | O1—C6—C7—N2 | 45.0 (2) |
N1i—Cu1—N2—C7 | −131.4 (1) | C5—C6—C7—N2 | −68.8 (2) |
O1—Cu1—N2—C7 | −25.3 (1) | O2—C6—C7—C8 | −9.9 (3) |
O1i—Cu1—N2—C7 | 154.7 (1) | O1—C6—C7—C8 | −135.3 (2) |
C5—N1—C1—C2 | −0.4 (3) | C5—C6—C7—C8 | 110.9 (2) |
Cu1—N1—C1—C2 | 179.6 (2) | N2—C7—C8—C9 | −1.2 (3) |
N1—C1—C2—C3 | −0.2 (4) | C6—C7—C8—C9 | 179.1 (2) |
C1—C2—C3—C4 | 0.9 (4) | C7—C8—C9—C10 | 1.1 (4) |
C2—C3—C4—C5 | −0.9 (4) | C8—C9—C10—C11 | −0.5 (4) |
C1—N1—C5—C4 | 0.3 (3) | C7—N2—C11—C10 | 0.1 (3) |
Cu1—N1—C5—C4 | −179.6 (2) | Cu1—N2—C11—C10 | 179.3 (2) |
C1—N1—C5—C6 | −178.5 (2) | C9—C10—C11—N2 | −0.1 (4) |
Cu1—N1—C5—C6 | 1.5 (2) |
Symmetry code: (i) −x+1/2, −y+3/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O3 | 0.82 | 2.19 | 2.564 (2) | 108 |
O2—H2o···O4 | 0.82 | 1.83 | 2.643 (2) | 171 |
O1w—H1w1···O3 | 0.82 | 1.93 | 2.738 (3) | 171 |
O2w—H2w1···O4ii | 0.83 | 2.05 | 2.790 (3) | 149 |
Symmetry code: (ii) x, y+1, z. |
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