In the title compound, (C2H8N)2[Cu(C2O4)2(H2O)]·H2O, the cations, anions and water molecules are linked by hydrogen bonds into a network structure. Two oxalate dianions and one water molecule are coordinated to the Cu atom and the geometry is square pyramidal.
Supporting information
CCDC reference: 289783
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.073
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O2 .. 5.22 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O5 .. 5.06 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O9 .. 8.51 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.16
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.55 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C3 - C4 ... 1.55 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O6 .. C4 .. 2.96 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C4 .. C4 .. 3.18 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.
Bis(dimethylammonium) aquadioxalatocuprate(II) monohydrate
top
Crystal data top
(C2H8N)2[Cu(C2O4)2(H2O)]·H2O | F(000) = 764 |
Mr = 367.81 | Dx = 1.604 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p2ybc | Cell parameters from 2706 reflections |
a = 11.7600 (16) Å | θ = 2.0–25.1° |
b = 9.5328 (13) Å | µ = 1.48 mm−1 |
c = 15.3997 (16) Å | T = 298 K |
β = 118.103 (8)° | Prism, blue |
V = 1522.9 (3) Å3 | 0.50 × 0.27 × 0.14 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2706 independent reflections |
Radiation source: fine-focus sealed tube | 2436 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 25.1°, θmin = 2.0° |
Absorption correction: numerical (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.63, Tmax = 0.81 | k = −11→11 |
7740 measured reflections | l = −18→10 |
Refinement top
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0421P)2 + 0.272P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2706 reflections | Δρmax = 0.28 e Å−3 |
192 parameters | Δρmin = −0.32 e Å−3 |
2 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0288 (13) |
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 | |
Cu1 | 0.74046 (2) | 0.50669 (2) | 0.026205 (15) | 0.03824 (12) | |
O1 | 0.84558 (12) | 0.62061 (16) | −0.01198 (9) | 0.0496 (4) | |
O2 | 0.84272 (12) | 0.59218 (14) | 0.15637 (8) | 0.0429 (3) | |
O3 | 1.01199 (13) | 0.73518 (15) | 0.23078 (9) | 0.0476 (3) | |
O4 | 1.02072 (13) | 0.75238 (15) | 0.05668 (10) | 0.0497 (4) | |
O5 | 0.62100 (12) | 0.45098 (14) | −0.10714 (9) | 0.0400 (3) | |
O6 | 0.62717 (11) | 0.40339 (12) | 0.06348 (8) | 0.0342 (3) | |
O7 | 0.45359 (13) | 0.26632 (14) | −0.00762 (9) | 0.0423 (3) | |
O8 | 0.44818 (12) | 0.31589 (14) | −0.18549 (9) | 0.0437 (3) | |
O9 | 0.87137 (13) | 0.30540 (17) | 0.06525 (10) | 0.0573 (4) | |
H9A | 0.9140 | 0.3077 | 0.0357 | 0.069* | |
H9B | 0.9122 | 0.2970 | 0.1252 | 0.069* | |
C1 | 0.93483 (16) | 0.68324 (18) | 0.05980 (12) | 0.0341 (4) | |
C2 | 0.93176 (16) | 0.67012 (18) | 0.15908 (12) | 0.0329 (4) | |
C3 | 0.53281 (15) | 0.37110 (17) | −0.11065 (12) | 0.0313 (4) | |
C4 | 0.53657 (16) | 0.34239 (17) | −0.00995 (12) | 0.0294 (4) | |
N1 | 0.79991 (14) | 0.42930 (16) | 0.29708 (11) | 0.0391 (4) | |
H1A | 0.7770 | 0.4650 | 0.2370 | 0.047* | |
H1B | 0.8660 | 0.3698 | 0.3119 | 0.047* | |
C5 | 0.8437 (2) | 0.5437 (2) | 0.36880 (19) | 0.0563 (6) | |
H5A | 0.8656 | 0.5070 | 0.4328 | 0.068* | |
H5B | 0.9182 | 0.5873 | 0.3702 | 0.068* | |
H5C | 0.7761 | 0.6118 | 0.3504 | 0.068* | |
C6 | 0.69093 (19) | 0.3506 (2) | 0.29342 (16) | 0.0509 (5) | |
H6A | 0.6210 | 0.4137 | 0.2801 | 0.061* | |
H6B | 0.6635 | 0.2813 | 0.2423 | 0.061* | |
H6C | 0.7168 | 0.3051 | 0.3555 | 0.061* | |
N2 | 0.32443 (14) | 0.43850 (16) | 0.33645 (11) | 0.0391 (4) | |
H2A | 0.3927 | 0.4876 | 0.3416 | 0.047* | |
H2B | 0.3522 | 0.3518 | 0.3602 | 0.047* | |
C7 | 0.2289 (2) | 0.4275 (2) | 0.23194 (15) | 0.0513 (5) | |
H7A | 0.1568 | 0.3728 | 0.2256 | 0.077* | |
H7B | 0.2675 | 0.3829 | 0.1964 | 0.077* | |
H7C | 0.1999 | 0.5196 | 0.2056 | 0.077* | |
C8 | 0.2743 (3) | 0.5066 (2) | 0.39729 (18) | 0.0564 (6) | |
H8A | 0.2536 | 0.6027 | 0.3772 | 0.068* | |
H8B | 0.3386 | 0.5032 | 0.4652 | 0.068* | |
H8C | 0.1982 | 0.4585 | 0.3891 | 0.068* | |
O10 | 0.47194 (12) | 0.10469 (14) | 0.14593 (9) | 0.0472 (3) | |
H10A | 0.4657 | 0.1331 | 0.1934 | 0.057* | |
H10B | 0.4666 | 0.1687 | 0.1092 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.03723 (17) | 0.05527 (19) | 0.02213 (16) | −0.01639 (10) | 0.01391 (12) | −0.00406 (9) |
O1 | 0.0519 (8) | 0.0723 (9) | 0.0240 (7) | −0.0302 (7) | 0.0173 (6) | −0.0070 (6) |
O2 | 0.0444 (7) | 0.0611 (8) | 0.0253 (7) | −0.0151 (6) | 0.0181 (6) | −0.0046 (6) |
O3 | 0.0454 (7) | 0.0641 (9) | 0.0299 (7) | −0.0153 (7) | 0.0151 (6) | −0.0162 (6) |
O4 | 0.0523 (8) | 0.0638 (9) | 0.0384 (8) | −0.0272 (7) | 0.0258 (7) | −0.0128 (6) |
O5 | 0.0398 (7) | 0.0556 (7) | 0.0249 (6) | −0.0150 (6) | 0.0155 (5) | −0.0026 (6) |
O6 | 0.0352 (6) | 0.0439 (7) | 0.0246 (6) | −0.0049 (5) | 0.0149 (5) | −0.0003 (5) |
O7 | 0.0502 (7) | 0.0446 (7) | 0.0363 (7) | −0.0150 (6) | 0.0238 (6) | −0.0014 (5) |
O8 | 0.0464 (7) | 0.0538 (8) | 0.0276 (7) | −0.0180 (6) | 0.0148 (6) | −0.0078 (6) |
O9 | 0.0517 (8) | 0.0879 (11) | 0.0382 (8) | 0.0197 (8) | 0.0260 (7) | 0.0142 (7) |
C1 | 0.0366 (9) | 0.0381 (9) | 0.0267 (9) | −0.0060 (8) | 0.0142 (8) | −0.0020 (7) |
C2 | 0.0316 (9) | 0.0388 (9) | 0.0276 (9) | 0.0008 (7) | 0.0133 (8) | −0.0030 (7) |
C3 | 0.0330 (9) | 0.0340 (9) | 0.0276 (9) | −0.0003 (7) | 0.0148 (7) | 0.0005 (7) |
C4 | 0.0336 (8) | 0.0272 (8) | 0.0305 (9) | 0.0022 (7) | 0.0177 (7) | 0.0021 (6) |
N1 | 0.0416 (8) | 0.0413 (9) | 0.0365 (9) | 0.0079 (7) | 0.0203 (7) | 0.0093 (7) |
C5 | 0.0522 (12) | 0.0451 (11) | 0.0614 (15) | −0.0079 (10) | 0.0182 (11) | −0.0055 (10) |
C6 | 0.0426 (11) | 0.0468 (11) | 0.0575 (13) | −0.0062 (9) | 0.0189 (10) | −0.0021 (9) |
N2 | 0.0417 (8) | 0.0376 (8) | 0.0361 (9) | 0.0066 (7) | 0.0168 (7) | 0.0039 (6) |
C7 | 0.0535 (12) | 0.0562 (13) | 0.0359 (11) | −0.0052 (10) | 0.0142 (9) | 0.0001 (9) |
C8 | 0.0657 (15) | 0.0612 (14) | 0.0463 (14) | 0.0095 (10) | 0.0298 (12) | −0.0040 (9) |
O10 | 0.0595 (8) | 0.0508 (8) | 0.0355 (7) | −0.0018 (7) | 0.0260 (7) | 0.0042 (6) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9334 (12) | N1—H1B | 0.9000 |
Cu1—O2 | 1.9640 (12) | C5—H5A | 0.9600 |
Cu1—O5 | 1.9377 (12) | C5—H5B | 0.9600 |
Cu1—O6 | 1.9480 (11) | C5—H5C | 0.9599 |
Cu1—O9 | 2.3540 (15) | C6—H6A | 0.9600 |
O1—C1 | 1.260 (2) | C6—H6B | 0.9600 |
O2—C2 | 1.268 (2) | C6—H6C | 0.9600 |
O3—C2 | 1.230 (2) | N2—C7 | 1.470 (2) |
O4—C1 | 1.226 (2) | N2—C8 | 1.472 (3) |
O5—C3 | 1.267 (2) | N2—H2A | 0.9001 |
O6—C4 | 1.272 (2) | N2—H2B | 0.9000 |
O7—C4 | 1.230 (2) | C7—H7A | 0.9600 |
O8—C3 | 1.231 (2) | C7—H7B | 0.9600 |
O9—H9A | 0.8201 | C7—H7C | 0.9600 |
O9—H9B | 0.8200 | C8—H8A | 0.9600 |
C1—C2 | 1.551 (2) | C8—H8B | 0.9600 |
C3—C4 | 1.555 (2) | C8—H8C | 0.9600 |
N1—C5 | 1.462 (3) | O10—H10A | 0.8142 |
N1—C6 | 1.463 (2) | O10—H10B | 0.8136 |
N1—H1A | 0.9000 | | |
| | | |
O1—Cu1—O2 | 84.57 (5) | C6—N1—H1B | 108.8 |
O1—Cu1—O5 | 94.58 (5) | H1A—N1—H1B | 107.7 |
O1—Cu1—O6 | 176.01 (6) | N1—C5—H5A | 109.5 |
O1—Cu1—O9 | 95.78 (6) | N1—C5—H5B | 109.5 |
O2—Cu1—O5 | 170.07 (6) | H5A—C5—H5B | 109.5 |
O2—Cu1—O6 | 94.82 (5) | N1—C5—H5C | 109.5 |
O2—Cu1—O9 | 93.74 (5) | H5A—C5—H5C | 109.5 |
O5—Cu1—O6 | 85.34 (5) | H5B—C5—H5C | 109.5 |
O5—Cu1—O9 | 96.19 (6) | N1—C6—H6A | 109.5 |
O6—Cu1—O9 | 88.19 (5) | N1—C6—H6B | 109.5 |
C1—O1—Cu1 | 112.78 (11) | H6A—C6—H6B | 109.5 |
C2—O2—Cu1 | 112.07 (11) | N1—C6—H6C | 109.5 |
C3—O5—Cu1 | 112.34 (10) | H6A—C6—H6C | 109.5 |
C4—O6—Cu1 | 111.84 (10) | H6B—C6—H6C | 109.5 |
Cu1—O9—H9A | 109.5 | C7—N2—C8 | 113.57 (17) |
Cu1—O9—H9B | 109.5 | C7—N2—H2A | 108.8 |
H9A—O9—H9B | 116.2 | C8—N2—H2A | 108.8 |
O4—C1—O1 | 125.57 (16) | C7—N2—H2B | 108.9 |
O4—C1—C2 | 118.95 (15) | C8—N2—H2B | 108.9 |
O1—C1—C2 | 115.47 (15) | H2A—N2—H2B | 107.7 |
O3—C2—O2 | 126.67 (16) | N2—C7—H7A | 109.5 |
O3—C2—C1 | 118.69 (15) | N2—C7—H7B | 109.5 |
O2—C2—C1 | 114.64 (14) | H7A—C7—H7B | 109.5 |
O8—C3—O5 | 125.56 (15) | N2—C7—H7C | 109.5 |
O8—C3—C4 | 119.28 (15) | H7A—C7—H7C | 109.5 |
O5—C3—C4 | 115.16 (14) | H7B—C7—H7C | 109.5 |
O7—C4—O6 | 125.99 (15) | N2—C8—H8A | 109.5 |
O7—C4—C3 | 118.87 (15) | N2—C8—H8B | 109.5 |
O6—C4—C3 | 115.13 (14) | H8A—C8—H8B | 109.5 |
C5—N1—C6 | 113.70 (17) | N2—C8—H8C | 109.4 |
C5—N1—H1A | 108.8 | H8A—C8—H8C | 109.5 |
C6—N1—H1A | 108.8 | H8B—C8—H8C | 109.5 |
C5—N1—H1B | 108.8 | H10A—O10—H10B | 111.3 |
| | | |
O5—Cu1—O1—C1 | 176.49 (13) | Cu1—O2—C2—O3 | −178.71 (15) |
O2—Cu1—O1—C1 | 6.42 (13) | Cu1—O2—C2—C1 | 2.21 (18) |
O9—Cu1—O1—C1 | −86.80 (14) | O4—C1—C2—O3 | 3.5 (3) |
O1—Cu1—O2—C2 | −4.58 (12) | O1—C1—C2—O3 | −176.02 (16) |
O6—Cu1—O2—C2 | 179.37 (12) | O4—C1—C2—O2 | −177.33 (16) |
O9—Cu1—O2—C2 | 90.87 (12) | O1—C1—C2—O2 | 3.1 (2) |
O1—Cu1—O5—C3 | −179.68 (12) | Cu1—O5—C3—O8 | −176.63 (14) |
O6—Cu1—O5—C3 | −3.68 (12) | Cu1—O5—C3—C4 | 2.77 (18) |
O9—Cu1—O5—C3 | 83.99 (12) | Cu1—O6—C4—O7 | 177.49 (15) |
O5—Cu1—O6—C4 | 3.93 (11) | Cu1—O6—C4—C3 | −3.41 (17) |
O2—Cu1—O6—C4 | 173.97 (11) | O8—C3—C4—O7 | −0.9 (2) |
O9—Cu1—O6—C4 | −92.43 (11) | O5—C3—C4—O7 | 179.64 (16) |
Cu1—O1—C1—O4 | 173.69 (16) | O8—C3—C4—O6 | 179.91 (15) |
Cu1—O1—C1—C2 | −6.8 (2) | O5—C3—C4—O6 | 0.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10B···O7 | 0.81 | 1.97 | 2.7443 (18) | 160 |
O10—H10A···O8i | 0.81 | 2.03 | 2.8415 (18) | 174 |
N2—H2B···O8i | 0.90 | 2.25 | 2.929 (2) | 132 |
N2—H2B···O7i | 0.90 | 2.13 | 2.907 (2) | 144 |
N2—H2A···O10ii | 0.90 | 1.88 | 2.776 (2) | 175 |
N1—H1B···O3iii | 0.90 | 2.24 | 3.065 (2) | 152 |
N1—H1B···O4iii | 0.90 | 2.14 | 2.809 (2) | 130 |
N1—H1A···O6 | 0.90 | 2.48 | 3.2006 (19) | 137 |
N1—H1A···O2 | 0.90 | 2.12 | 2.896 (2) | 143 |
O9—H9B···O3iii | 0.82 | 2.05 | 2.8525 (19) | 167 |
O9—H9A···O4iv | 0.82 | 1.99 | 2.7722 (19) | 158 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, −y+1, −z. |