The molecule of the title compound, [Cu(7HtpO)
2(NO
3)
2(H
2O)
2], contains two neutral 4,7-dihydro-1,2,4-triazolo[1,5-
a]pyrimidin-7-one (7HtpO) ligands , coordinated through the N atom in position 3, two nitrate ions each coordinated through one of the O atoms, and two water molecules, completing the octahedral environment around the copper atom which lies on an inversion centre, thus defining the all-
trans isomer. The intramolecular N—H
O hydrogen bond involving the nitrate oxygen atom linked to the metal atom stabilizes the structure. Distances in the coordination sphere are Cu—N(7HtpO)= 2.003 (2), Cu—O(nitrate) = 2.410 (2) and Cu—O(water) = 1.977 (2) Å.
Supporting information
CCDC reference: 225671
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.166
- Data-to-parameter ratio = 20.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N1N
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: STADI4 (STOE, 1996); cell refinement: STADI4; data reduction: X-RED (STOE, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XtalGX (Hall & du Boulay, 1997); software used to prepare material for publication: SHELXL97.
Crystal data top
[Cu(C5H4N4O)2(NO3)2(H2O)2] | Dx = 1.916 Mg m−3 |
Mr = 495.84 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 40 reflections |
a = 14.4717 (5) Å | θ = 12.7–17.6° |
b = 6.4247 (2) Å | µ = 1.36 mm−1 |
c = 18.4846 (6) Å | T = 293 K |
V = 1718.63 (10) Å3 | Brick-shaped, blue |
Z = 4 | 0.55 × 0.38 × 0.25 mm |
F(000) = 1004 | |
Data collection top
STOE STADI4 4-circle diffractometer | 2141 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 32.5°, θmin = 2.2° |
Scan width (ω) = 1.05 – 1.25, scan ratio 2θ:ω = 1.00 | h = 0→21 |
Absorption correction: ψ scan (X-RED; Stoe, 1996) | k = 0→9 |
Tmin = 0.569, Tmax = 0.704 | l = 0→27 |
3096 measured reflections | 3 standard reflections every 60 min |
3096 independent reflections | intensity decay: 4.0% |
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)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.166 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2) + (0.065P)2 + 3.5P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.002 |
3096 reflections | Δρmax = 0.94 e Å−3 |
149 parameters | Δρmin = −0.65 e Å−3 |
2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: heavy-atom method | Extinction coefficient: 0.0078 (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 | 0.5000 | 0.5000 | 0.5000 | 0.0276 (2) | |
N1 | 0.5490 (2) | 0.0712 (4) | 0.33448 (14) | 0.0393 (6) | |
C2 | 0.5189 (2) | 0.1410 (5) | 0.3969 (2) | 0.0375 (6) | |
H2 | 0.4894 | 0.0560 | 0.4304 | 0.045* | |
N3 | 0.5341 (2) | 0.3490 (4) | 0.40906 (12) | 0.0307 (5) | |
C3A | 0.5769 (2) | 0.4102 (4) | 0.34914 (15) | 0.0311 (5) | |
N4 | 0.6091 (2) | 0.5978 (4) | 0.3301 (2) | 0.0415 (6) | |
H4 | 0.6048 | 0.7019 | 0.3592 | 0.050* | |
C5 | 0.6487 (2) | 0.6202 (6) | 0.2636 (2) | 0.0456 (8) | |
H5 | 0.6712 | 0.7502 | 0.2502 | 0.055* | |
C6 | 0.6564 (3) | 0.4609 (6) | 0.2165 (2) | 0.0451 (7) | |
H6 | 0.6849 | 0.4838 | 0.1721 | 0.054* | |
C7 | 0.6220 (2) | 0.2581 (5) | 0.2329 (2) | 0.0354 (6) | |
O7 | 0.6210 (2) | 0.1020 (4) | 0.19453 (12) | 0.0458 (6) | |
N8 | 0.5860 (2) | 0.2468 (4) | 0.30352 (12) | 0.0317 (5) | |
N1N | 0.3085 (2) | 0.2281 (5) | 0.5033 (2) | 0.0455 (7) | |
O1N | 0.3890 (2) | 0.2359 (4) | 0.53173 (13) | 0.0403 (5) | |
O2N | 0.2998 (2) | 0.2337 (6) | 0.4369 (2) | 0.0764 (10) | |
O3N | 0.2405 (2) | 0.2160 (6) | 0.5432 (2) | 0.0724 (10) | |
O1W | 0.59055 (15) | 0.3231 (4) | 0.55131 (12) | 0.0359 (5) | |
H11W | 0.6388 (19) | 0.295 (7) | 0.5275 (19) | 0.043* | |
H12W | 0.603 (3) | 0.364 (6) | 0.5942 (12) | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.0306 (3) | 0.0281 (2) | 0.0242 (2) | 0.0033 (2) | 0.0003 (2) | −0.0024 (2) |
N1 | 0.056 (2) | 0.0270 (11) | 0.0348 (12) | −0.0019 (11) | 0.0075 (11) | −0.0016 (10) |
C2 | 0.052 (2) | 0.0283 (13) | 0.0324 (13) | 0.0004 (12) | 0.0044 (12) | 0.0012 (11) |
N3 | 0.0363 (11) | 0.0272 (10) | 0.0286 (10) | 0.0014 (9) | 0.0026 (9) | −0.0008 (8) |
C3A | 0.0369 (13) | 0.0254 (11) | 0.0311 (12) | −0.0006 (10) | −0.0003 (10) | −0.0015 (10) |
N4 | 0.0485 (15) | 0.0299 (12) | 0.0462 (14) | −0.0062 (11) | 0.0080 (12) | −0.0032 (11) |
C5 | 0.047 (2) | 0.038 (2) | 0.052 (2) | −0.0041 (14) | 0.0090 (15) | 0.0102 (14) |
C6 | 0.049 (2) | 0.049 (2) | 0.037 (2) | −0.0034 (15) | 0.0081 (14) | 0.0069 (14) |
C7 | 0.0393 (14) | 0.040 (2) | 0.0265 (11) | 0.0033 (12) | −0.0001 (10) | 0.0006 (11) |
O7 | 0.063 (2) | 0.0453 (13) | 0.0295 (10) | 0.0042 (12) | 0.0037 (10) | −0.0071 (9) |
N8 | 0.0403 (12) | 0.0282 (10) | 0.0266 (10) | 0.0017 (10) | 0.0056 (9) | −0.0017 (8) |
N1N | 0.0356 (13) | 0.0348 (13) | 0.066 (2) | −0.0054 (11) | −0.0011 (13) | −0.0082 (13) |
O1N | 0.0351 (10) | 0.0405 (12) | 0.0454 (12) | −0.0035 (9) | −0.0016 (9) | −0.0002 (10) |
O2N | 0.071 (2) | 0.100 (3) | 0.058 (2) | −0.006 (2) | −0.023 (2) | −0.009 (2) |
O3N | 0.048 (2) | 0.085 (2) | 0.084 (2) | −0.012 (2) | 0.015 (2) | −0.012 (2) |
O1W | 0.0361 (10) | 0.0394 (11) | 0.0321 (10) | 0.0065 (9) | −0.0018 (8) | −0.0022 (9) |
Geometric parameters (Å, º) top
Cu—O1W | 1.977 (2) | C5—C6 | 1.348 (5) |
Cu—N3 | 2.003 (2) | C5—H5 | 0.9300 |
Cu—O1N | 2.410 (2) | C6—C7 | 1.427 (5) |
N1—C2 | 1.312 (4) | C6—H6 | 0.9300 |
N1—N8 | 1.374 (4) | C7—O7 | 1.228 (4) |
C2—N3 | 1.373 (4) | C7—N8 | 1.408 (4) |
C2—H2 | 0.9300 | N1N—O3N | 1.232 (4) |
N3—C3A | 1.328 (4) | N1N—O2N | 1.234 (4) |
C3A—N4 | 1.339 (4) | N1N—O1N | 1.278 (4) |
C3A—N8 | 1.353 (4) | O1W—H11W | 0.844 (18) |
N4—C5 | 1.364 (4) | O1W—H12W | 0.853 (18) |
N4—H4 | 0.8600 | | |
| | | |
O1W—Cu—N3 | 87.75 (9) | N4—C5—H5 | 118.8 |
O1W—Cu—O1N | 85.44 (9) | C5—C6—C7 | 121.8 (3) |
N3—Cu—O1N | 91.59 (9) | C5—C6—H6 | 119.1 |
C2—N1—N8 | 102.4 (2) | C7—C6—H6 | 119.0 |
N1—C2—N3 | 115.1 (3) | O7—C7—N8 | 119.3 (3) |
N1—C2—H2 | 122.5 | O7—C7—C6 | 128.9 (3) |
N3—C2—H2 | 122.4 | N8—C7—C6 | 111.9 (3) |
C3A—N3—C2 | 103.1 (2) | C3A—N8—N1 | 109.9 (2) |
C3A—N3—Cu | 132.2 (2) | C3A—N8—C7 | 125.0 (3) |
C2—N3—Cu | 124.7 (2) | N1—N8—C7 | 125.0 (2) |
N3—C3A—N4 | 130.4 (3) | O3N—N1N—O2N | 121.0 (3) |
N3—C3A—N8 | 109.6 (2) | O3N—N1N—O1N | 119.0 (3) |
N4—C3A—N8 | 120.0 (3) | O2N—N1N—O1N | 120.1 (3) |
C3A—N4—C5 | 118.6 (3) | N1N—O1N—Cu | 122.3 (2) |
C3A—N4—H4 | 120.7 | Cu—O1W—H11W | 115 (3) |
C5—N4—H4 | 120.7 | Cu—O1W—H12W | 114 (3) |
C6—C5—N4 | 122.4 (3) | H11W—O1W—H12W | 113 (4) |
C6—C5—H5 | 118.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O1Ni | 0.86 | 2.06 | 2.769 (4) | 140 (1) |
O1W—H11W···O3Nii | 0.84 (2) | 1.97 (2) | 2.797 (4) | 166 (3) |
O1W—H12W···O7iii | 0.85 (2) | 1.89 (1) | 2.727 (3) | 168 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+1/2, −z+1; (iii) x, −y+1/2, z+1/2. |