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In the title compound, (C2H8N)2[Cu2(C5HN2O4)2(H2O)2]·H2O, the cations, anions and water mol­ecules are linked by hydrogen bonds into a network structure. Two pyrazole-3,5-dicarboxyl­ate trianions and one water mol­ecule are coordinated to the CuII ion and the geometry is square-pyramidal. Each pair of CuII ions is bridged by two pyrazole-3,5-dicarboxyl­ate trianions, forming a dinuclear ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034410/sj6140sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034410/sj6140Isup2.hkl
Contains datablock I

CCDC reference: 289892

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.046
  • wR factor = 0.109
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for N6 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.25 PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. O3 .. 2.65 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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) di-µ-pyrazole-3,5-dicarboxylato(3-)-bis[aquacopper(II)] monohydrate top
Crystal data top
(C2H8N)2[Cu2(C5HN2O4)2(H2O)2]·H2OZ = 2
Mr = 579.47F(000) = 592
Triclinic, P1Dx = 1.788 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2094 (7) ÅCell parameters from 5717 reflections
b = 10.6365 (8) Åθ = 1.9–25.1°
c = 12.6853 (10) ŵ = 2.05 mm1
α = 109.775 (1)°T = 298 K
β = 111.109 (1)°Block, blue
γ = 91.252 (2)°0.48 × 0.25 × 0.22 mm
V = 1076.14 (14) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3760 independent reflections
Radiation source: fine-focus sealed tube3371 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
600 frames, δ ω = 2° scansθmax = 25.1°, θmin = 1.9°
Absorption correction: numerical
(SADABS; Bruker, 2002)
h = 1010
Tmin = 0.540, Tmax = 0.632k = 1112
5717 measured reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0462P)2 + 2.5226P]
where P = (Fo2 + 2Fc2)/3
3760 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 1.38 e Å3
2 restraintsΔρmin = 1.51 e Å3
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
xyzUiso*/Ueq
C120.7371 (7)0.7724 (6)0.1231 (6)0.0729 (18)
H12A0.82900.80850.19760.109*
H12B0.64770.80860.13620.109*
H12C0.75410.79700.06180.109*
C110.8208 (8)0.5553 (6)0.0555 (6)0.0779 (19)
H11A0.78030.46070.02650.117*
H11B0.91680.57800.12650.117*
H11C0.84170.57480.00680.117*
N60.7087 (10)0.6326 (6)0.0852 (8)0.135 (3)
H6A0.61720.60260.01930.162*
H6B0.69270.61300.14420.162*
C130.2417 (7)0.9365 (6)0.9536 (5)0.0637 (16)
H13A0.25971.00721.03020.096*
H13B0.16570.95690.88900.096*
H13C0.33900.93010.94180.096*
C140.0409 (6)0.8122 (6)0.9817 (4)0.0532 (13)
H14A0.04180.83480.92240.080*
H14B0.06520.87961.06110.080*
H14C0.00700.72540.98020.080*
N50.1818 (4)0.8071 (4)0.9531 (3)0.0384 (8)
H5A0.15870.74250.87920.046*
H5B0.25800.78381.00790.046*
O110.1179 (4)0.8691 (3)0.6140 (3)0.0412 (7)
Cu10.43815 (5)0.24640 (5)0.31599 (4)0.02859 (15)
Cu20.75411 (5)0.37432 (5)0.65608 (4)0.02953 (16)
O70.2335 (3)0.1180 (3)0.2459 (2)0.0311 (6)
O50.7415 (3)0.3234 (3)0.7927 (2)0.0334 (6)
O10.4223 (3)0.3279 (3)0.1914 (3)0.0387 (7)
O30.9302 (3)0.5325 (3)0.7369 (2)0.0349 (7)
N40.7236 (4)0.4314 (3)0.5220 (3)0.0334 (8)
N10.4523 (4)0.2069 (3)0.4560 (3)0.0293 (7)
N20.5578 (4)0.2506 (3)0.5706 (3)0.0301 (7)
N30.6173 (4)0.3888 (4)0.4078 (3)0.0327 (8)
O80.0902 (3)0.0115 (3)0.2917 (2)0.0325 (6)
O100.9274 (4)0.2250 (3)0.6306 (3)0.0408 (7)
H10B0.91680.19560.55920.061*
H10A0.91040.16310.65160.061*
C100.6208 (5)0.2383 (4)0.7631 (3)0.0293 (9)
O41.0542 (3)0.6848 (3)0.7013 (2)0.0358 (7)
O60.5924 (3)0.1926 (3)0.8332 (2)0.0382 (7)
C60.2088 (4)0.0706 (4)0.3196 (3)0.0250 (8)
C50.9461 (5)0.5909 (4)0.6679 (3)0.0286 (8)
C20.6488 (4)0.4670 (4)0.3535 (3)0.0268 (8)
C90.5083 (4)0.1935 (4)0.6329 (3)0.0266 (8)
O20.5518 (4)0.4778 (4)0.1564 (3)0.0575 (10)
C70.3339 (4)0.1220 (4)0.4444 (3)0.0262 (8)
O90.5552 (3)0.0737 (3)0.2348 (3)0.0403 (7)
H9B0.51380.00220.23060.060*
H9A0.64860.08630.27980.060*
C10.5346 (5)0.4240 (4)0.2244 (4)0.0347 (10)
C40.8238 (4)0.5377 (4)0.5408 (3)0.0260 (8)
C80.3643 (4)0.1086 (4)0.5559 (3)0.0279 (8)
H80.30300.05550.57450.033*
C30.7808 (4)0.5642 (4)0.4347 (4)0.0283 (8)
H30.82920.63140.42110.034*
H11D0.103 (6)0.805 (4)0.632 (4)0.042*
H11E0.061 (5)0.920 (4)0.637 (4)0.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C120.051 (3)0.055 (3)0.093 (5)0.012 (3)0.024 (3)0.008 (3)
C110.102 (5)0.051 (3)0.069 (4)0.027 (3)0.021 (4)0.020 (3)
N60.214 (9)0.052 (3)0.200 (8)0.008 (4)0.169 (8)0.027 (4)
C130.084 (4)0.058 (3)0.039 (3)0.010 (3)0.011 (3)0.021 (3)
C140.050 (3)0.063 (3)0.038 (3)0.008 (3)0.012 (2)0.015 (2)
N50.045 (2)0.040 (2)0.0213 (17)0.0042 (17)0.0048 (16)0.0099 (15)
O110.0418 (18)0.045 (2)0.0474 (19)0.0070 (15)0.0246 (15)0.0228 (16)
Cu10.0254 (3)0.0363 (3)0.0186 (3)0.0077 (2)0.00021 (19)0.0140 (2)
Cu20.0289 (3)0.0337 (3)0.0183 (3)0.0086 (2)0.0003 (2)0.0115 (2)
O70.0255 (14)0.0419 (16)0.0207 (13)0.0046 (12)0.0006 (11)0.0151 (12)
O50.0333 (15)0.0391 (16)0.0211 (14)0.0069 (13)0.0031 (12)0.0120 (12)
O10.0348 (16)0.0462 (18)0.0278 (15)0.0120 (13)0.0022 (13)0.0218 (14)
O30.0382 (16)0.0335 (15)0.0215 (14)0.0109 (12)0.0005 (12)0.0108 (12)
N40.0338 (18)0.0357 (19)0.0208 (17)0.0104 (15)0.0021 (14)0.0133 (15)
N10.0267 (17)0.0383 (19)0.0162 (16)0.0076 (14)0.0003 (13)0.0124 (14)
N20.0300 (17)0.0365 (19)0.0187 (16)0.0057 (14)0.0016 (14)0.0135 (14)
N30.0313 (18)0.040 (2)0.0207 (17)0.0087 (15)0.0012 (14)0.0169 (15)
O80.0243 (14)0.0343 (15)0.0311 (15)0.0079 (12)0.0028 (12)0.0121 (12)
O100.0504 (18)0.0366 (17)0.0349 (17)0.0009 (14)0.0147 (15)0.0150 (14)
C100.034 (2)0.029 (2)0.023 (2)0.0026 (17)0.0079 (17)0.0112 (17)
O40.0365 (16)0.0337 (16)0.0254 (15)0.0117 (13)0.0048 (12)0.0057 (12)
O60.0407 (17)0.0480 (18)0.0248 (15)0.0066 (14)0.0054 (13)0.0209 (14)
C60.0229 (19)0.0254 (19)0.0252 (19)0.0036 (16)0.0070 (16)0.0105 (16)
C50.029 (2)0.026 (2)0.024 (2)0.0003 (17)0.0066 (17)0.0060 (16)
C20.028 (2)0.029 (2)0.025 (2)0.0023 (16)0.0077 (16)0.0140 (17)
C90.029 (2)0.030 (2)0.0170 (18)0.0014 (16)0.0048 (16)0.0094 (16)
O20.056 (2)0.073 (2)0.0358 (18)0.0264 (18)0.0033 (16)0.0357 (18)
C70.0256 (19)0.028 (2)0.0242 (19)0.0002 (16)0.0090 (16)0.0102 (16)
O90.0350 (16)0.0371 (17)0.0471 (19)0.0007 (13)0.0138 (15)0.0164 (15)
C10.034 (2)0.042 (2)0.027 (2)0.0022 (19)0.0033 (18)0.0198 (19)
C40.0236 (19)0.0251 (19)0.024 (2)0.0028 (15)0.0047 (16)0.0086 (16)
C80.028 (2)0.030 (2)0.025 (2)0.0014 (16)0.0071 (16)0.0141 (17)
C30.031 (2)0.026 (2)0.031 (2)0.0015 (16)0.0096 (17)0.0167 (17)
Geometric parameters (Å, º) top
C12—N61.385 (8)Cu2—O52.022 (3)
C12—H12A0.9600Cu2—O102.304 (3)
C12—H12B0.9600O7—C61.283 (4)
C12—H12C0.9600O5—C101.273 (5)
C11—N61.411 (9)O1—C11.281 (5)
C11—H11A0.9600O3—C51.276 (5)
C11—H11B0.9600N4—N31.333 (4)
C11—H11C0.9600N4—C41.342 (5)
N6—H6A0.9000N1—C71.334 (5)
N6—H6B0.9000N1—N21.334 (4)
C13—N51.469 (6)N2—C91.331 (5)
C13—H13A0.9600N3—C21.332 (5)
C13—H13B0.9600O8—C61.246 (4)
C13—H13C0.9600O10—H10B0.8200
C14—N51.465 (6)O10—H10A0.8202
C14—H14A0.9600C10—O61.245 (5)
C14—H14B0.9600C10—C91.497 (5)
C14—H14C0.9600O4—C51.238 (5)
N5—H5A0.9000C6—C71.485 (5)
N5—H5B0.9000C5—C41.495 (5)
O11—H11D0.81 (3)C2—C31.389 (5)
O11—H11E0.81 (3)C2—C11.492 (5)
Cu1—N31.920 (3)C9—C81.394 (5)
Cu1—N11.920 (3)O2—C11.235 (5)
Cu1—O12.009 (3)C7—C81.398 (5)
Cu1—O72.016 (3)O9—H9B0.8200
Cu1—O92.282 (3)O9—H9A0.8202
Cu2—N21.922 (3)C4—C31.388 (5)
Cu2—N41.923 (3)C8—H80.9300
Cu2—O32.007 (3)C3—H30.9300
N6—C12—H12A109.5O3—Cu2—O1091.02 (12)
N6—C12—H12B109.5O5—Cu2—O1090.07 (11)
H12A—C12—H12B109.5C6—O7—Cu1115.2 (2)
N6—C12—H12C109.5C10—O5—Cu2115.1 (2)
H12A—C12—H12C109.5C1—O1—Cu1115.1 (2)
H12B—C12—H12C109.5C5—O3—Cu2115.4 (2)
N6—C11—H11A109.5N3—N4—C4108.6 (3)
N6—C11—H11B109.5N3—N4—Cu2133.5 (3)
H11A—C11—H11B109.5C4—N4—Cu2117.9 (3)
N6—C11—H11C109.5C7—N1—N2108.8 (3)
H11A—C11—H11C109.5C7—N1—Cu1117.8 (2)
H11B—C11—H11C109.5N2—N1—Cu1133.4 (2)
C12—N6—C11120.2 (6)C9—N2—N1109.0 (3)
C12—N6—H6A107.3C9—N2—Cu2117.9 (3)
C11—N6—H6A107.3N1—N2—Cu2133.1 (2)
C12—N6—H6B107.3C2—N3—N4108.7 (3)
C11—N6—H6B107.3C2—N3—Cu1118.2 (3)
H6A—N6—H6B106.9N4—N3—Cu1133.1 (3)
N5—C13—H13A109.5Cu2—O10—H10B109.5
N5—C13—H13B109.5Cu2—O10—H10A109.4
H13A—C13—H13B109.5H10B—O10—H10A110.7
N5—C13—H13C109.5O6—C10—O5125.1 (4)
H13A—C13—H13C109.5O6—C10—C9120.0 (3)
H13B—C13—H13C109.5O5—C10—C9114.9 (3)
N5—C14—H14A109.5O8—C6—O7124.1 (3)
N5—C14—H14B109.5O8—C6—C7121.2 (3)
H14A—C14—H14B109.5O7—C6—C7114.7 (3)
N5—C14—H14C109.5O4—C5—O3123.6 (4)
H14A—C14—H14C109.5O4—C5—C4121.2 (3)
H14B—C14—H14C109.5O3—C5—C4115.2 (3)
C14—N5—C13113.0 (4)N3—C2—C3109.5 (3)
C14—N5—H5A109.0N3—C2—C1111.5 (3)
C13—N5—H5A109.0C3—C2—C1138.9 (3)
C14—N5—H5B109.0N2—C9—C8109.3 (3)
C13—N5—H5B109.0N2—C9—C10112.1 (3)
H5A—N5—H5B107.8C8—C9—C10138.7 (3)
H11D—O11—H11E104 (5)N1—C7—C8109.2 (3)
N3—Cu1—N193.04 (13)N1—C7—C6112.4 (3)
N3—Cu1—O179.95 (12)C8—C7—C6138.5 (3)
N1—Cu1—O1167.82 (14)Cu1—O9—H9B109.5
N3—Cu1—O7168.19 (14)Cu1—O9—H9A109.4
N1—Cu1—O779.95 (12)H9B—O9—H9A107.5
O1—Cu1—O7105.18 (11)O2—C1—O1124.0 (4)
N3—Cu1—O999.99 (14)O2—C1—C2121.0 (4)
N1—Cu1—O997.68 (13)O1—C1—C2115.0 (3)
O1—Cu1—O993.37 (12)N4—C4—C3109.2 (3)
O7—Cu1—O990.41 (11)N4—C4—C5111.3 (3)
N2—Cu2—N492.85 (13)C3—C4—C5139.5 (3)
N2—Cu2—O3167.80 (13)C9—C8—C7103.8 (3)
N4—Cu2—O380.07 (12)C9—C8—H8128.1
N2—Cu2—O579.99 (12)C7—C8—H8128.1
N4—Cu2—O5168.30 (14)C4—C3—C2104.0 (3)
O3—Cu2—O5105.26 (11)C4—C3—H3128.0
N2—Cu2—O10100.07 (13)C2—C3—H3128.0
N4—Cu2—O10100.35 (14)
N3—Cu1—O7—C655.2 (7)N1—Cu1—N3—N47.8 (4)
N1—Cu1—O7—C61.0 (3)O1—Cu1—N3—N4177.8 (4)
O1—Cu1—O7—C6169.6 (3)O7—Cu1—N3—N460.9 (8)
O9—Cu1—O7—C696.8 (3)O9—Cu1—N3—N490.6 (4)
N2—Cu2—O5—C100.8 (3)Cu2—O5—C10—O6178.9 (3)
N4—Cu2—O5—C1053.6 (7)Cu2—O5—C10—C91.1 (4)
O3—Cu2—O5—C10169.5 (3)Cu1—O7—C6—O8178.8 (3)
O10—Cu2—O5—C1099.4 (3)Cu1—O7—C6—C71.6 (4)
N3—Cu1—O1—C13.8 (3)Cu2—O3—C5—O4175.7 (3)
N1—Cu1—O1—C159.3 (7)Cu2—O3—C5—C44.1 (4)
O7—Cu1—O1—C1172.9 (3)N4—N3—C2—C30.2 (5)
O9—Cu1—O1—C195.8 (3)Cu1—N3—C2—C3179.3 (3)
N2—Cu2—O3—C558.0 (7)N4—N3—C2—C1179.5 (3)
N4—Cu2—O3—C52.8 (3)Cu1—N3—C2—C11.4 (5)
O5—Cu2—O3—C5172.1 (3)N1—N2—C9—C80.1 (5)
O10—Cu2—O3—C597.5 (3)Cu2—N2—C9—C8179.5 (3)
N2—Cu2—N4—N37.6 (4)N1—N2—C9—C10179.7 (3)
O3—Cu2—N4—N3177.6 (4)Cu2—N2—C9—C100.3 (5)
O5—Cu2—N4—N359.4 (9)O6—C10—C9—N2179.1 (4)
O10—Cu2—N4—N393.2 (4)O5—C10—C9—N21.0 (5)
N2—Cu2—N4—C4170.8 (3)O6—C10—C9—C81.2 (8)
O3—Cu2—N4—C40.8 (3)O5—C10—C9—C8178.8 (5)
O5—Cu2—N4—C4119.0 (6)N2—N1—C7—C80.7 (5)
O10—Cu2—N4—C488.4 (3)Cu1—N1—C7—C8178.8 (3)
N3—Cu1—N1—C7170.5 (3)N2—N1—C7—C6178.8 (3)
O1—Cu1—N1—C7116.1 (6)Cu1—N1—C7—C60.7 (4)
O7—Cu1—N1—C70.1 (3)O8—C6—C7—N1178.9 (3)
O9—Cu1—N1—C789.0 (3)O7—C6—C7—N11.5 (5)
N3—Cu1—N1—N27.0 (4)O8—C6—C7—C81.9 (7)
O1—Cu1—N1—N261.4 (8)O7—C6—C7—C8177.7 (4)
O7—Cu1—N1—N2177.4 (4)Cu1—O1—C1—O2173.4 (4)
O9—Cu1—N1—N293.5 (4)Cu1—O1—C1—C25.5 (5)
C7—N1—N2—C90.4 (5)N3—C2—C1—O2174.4 (4)
Cu1—N1—N2—C9178.0 (3)C3—C2—C1—O24.6 (8)
C7—N1—N2—Cu2178.9 (3)N3—C2—C1—O14.6 (5)
Cu1—N1—N2—Cu21.3 (6)C3—C2—C1—O1176.4 (5)
N4—Cu2—N2—C9170.9 (3)N3—N4—C4—C30.2 (5)
O3—Cu2—N2—C9116.8 (6)Cu2—N4—C4—C3179.0 (3)
O5—Cu2—N2—C90.2 (3)N3—N4—C4—C5179.8 (3)
O10—Cu2—N2—C988.1 (3)Cu2—N4—C4—C51.0 (5)
N4—Cu2—N2—N18.4 (4)O4—C5—C4—N4176.4 (4)
O3—Cu2—N2—N162.4 (8)O3—C5—C4—N43.4 (5)
O5—Cu2—N2—N1179.1 (4)O4—C5—C4—C33.6 (8)
O10—Cu2—N2—N192.7 (4)O3—C5—C4—C3176.6 (5)
C4—N4—N3—C20.0 (5)N2—C9—C8—C70.5 (4)
Cu2—N4—N3—C2178.5 (3)C10—C9—C8—C7179.3 (5)
C4—N4—N3—Cu1178.9 (3)N1—C7—C8—C90.7 (4)
Cu2—N4—N3—Cu10.4 (7)C6—C7—C8—C9178.5 (5)
N1—Cu1—N3—C2171.0 (3)N4—C4—C3—C20.3 (4)
O1—Cu1—N3—C21.1 (3)C5—C4—C3—C2179.6 (5)
O7—Cu1—N3—C2117.9 (6)N3—C2—C3—C40.3 (4)
O9—Cu1—N3—C290.6 (3)C1—C2—C3—C4179.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9B···O6i0.822.032.820 (4)162
O10—H10B···O11ii0.821.972.785 (5)177
O11—H11D···O4iii0.81 (3)1.91 (3)2.702 (4)166 (5)
O11—H11E···O8iv0.81 (3)2.02 (3)2.819 (4)166 (5)
O9—H9A···O11ii0.822.022.843 (4)175
O10—H10A···O8i0.821.982.787 (4)170
N5—H5B···O6v0.901.922.759 (4)155
N5—H5A···O3iii0.902.653.336 (4)134
N5—H5A···O4iii0.901.972.773 (4)148
N6—H6B···O20.902.002.731 (6)138
N6—H6A···O2vi0.902.072.945 (10)164
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x1, y, z; (iv) x, y+1, z+1; (v) x+1, y+1, z+2; (vi) x+1, y+1, z.
 

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