Bis(dimethyl­ammonium) aqua­dioxalatocuprate(II) monohydrate

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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

Crystal data

(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) Å^3	0.50 × 0.27 × 0.14 mm
Z = 4

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.272P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0288 (13)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O8^i	0.81	2.03	2.8415 (18)	174
N2—H2B···O8^i	0.90	2.25	2.929 (2)	132
N2—H2B···O7^i	0.90	2.13	2.907 (2)	144
N2—H2A···O10^ii	0.90	1.88	2.776 (2)	175
N1—H1B···O3^iii	0.90	2.24	3.065 (2)	152
N1—H1B···O4^iii	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···O3^iii	0.82	2.05	2.8525 (19)	167
O9—H9A···O4^iv	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.