The crystal structure of the title compound, [Cu(C6H6N4)2(H2O)](NO3)2, has been determined from single-crystal X-ray diffraction data. The five-coordinate geometry of the copper(II) centre comprises four N atoms from two biimidazole ligands and a water molecule in a distorted square-based pyramidal coordination. Cu and the aqua ligand lie on a twofold rotation axis.
Supporting information
CCDC reference: 242514
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.039
- wR factor = 0.136
- Data-to-parameter ratio = 11.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.88
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O1 .. 2.64 Ang.
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.877
Tmax scaled 0.877 Tmin scaled 0.655
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
Data collection: SMART (Siemens, 1994); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.
Aquabis(2,2'-biimidazole)copper(II) dinitrate
top
Crystal data top
[Cu(C6H6N4)2(H2O)](NO3)2 | F(000) = 964 |
Mr = 473.88 | Dx = 1.797 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2339 reflections |
a = 19.6113 (19) Å | θ = 2.3–25.0° |
b = 6.8168 (7) Å | µ = 1.31 mm−1 |
c = 14.2923 (14) Å | T = 293 K |
β = 113.551 (2)° | Block, green |
V = 1751.5 (3) Å3 | 0.40 × 0.32 × 0.10 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD diffractometer | 1525 independent reflections |
Radiation source: fine-focus sealed tube | 1387 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→12 |
Tmin = 0.747, Tmax = 1.000 | k = −6→8 |
2908 measured reflections | l = −16→17 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0934P)2 + 5.5585P] where P = (Fo2 + 2Fc2)/3 |
1525 reflections | (Δ/σ)max < 0.001 |
138 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
Special details top
Experimental. C, H and N were analyzed in a Vario EL III elemental analyzer. |
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 | 0.0000 | 0.37217 (9) | 0.2500 | 0.0291 (3) | |
O1 | 0.0000 | 0.6961 (6) | 0.2500 | 0.0522 (11) | |
N1 | −0.03329 (16) | 0.2980 (5) | 0.1004 (2) | 0.0313 (7) | |
N3 | 0.00193 (17) | 0.2409 (5) | −0.0245 (2) | 0.0336 (7) | |
H3 | 0.0301 | 0.2239 | −0.0570 | 0.040* | |
N2 | 0.10048 (16) | 0.3678 (4) | 0.2445 (2) | 0.0296 (7) | |
N4 | 0.16474 (17) | 0.3240 (5) | 0.1509 (2) | 0.0360 (7) | |
H4 | 0.1754 | 0.2955 | 0.0997 | 0.043* | |
C3 | 0.02435 (19) | 0.2801 (5) | 0.0753 (3) | 0.0291 (7) | |
C2 | −0.0742 (2) | 0.2327 (6) | −0.0651 (3) | 0.0386 (9) | |
H2 | −0.1052 | 0.2083 | −0.1329 | 0.046* | |
C1 | −0.0957 (2) | 0.2670 (6) | 0.0127 (3) | 0.0365 (9) | |
H1 | −0.1445 | 0.2691 | 0.0076 | 0.044* | |
C4 | 0.09728 (19) | 0.3172 (5) | 0.1534 (3) | 0.0281 (7) | |
C6 | 0.1740 (2) | 0.4113 (6) | 0.3024 (3) | 0.0370 (9) | |
H6 | 0.1932 | 0.4523 | 0.3701 | 0.044* | |
C5 | 0.2135 (2) | 0.3846 (6) | 0.2448 (3) | 0.0397 (9) | |
H5 | 0.2643 | 0.4040 | 0.2653 | 0.048* | |
O2 | 0.36845 (19) | 0.4050 (5) | 0.1925 (2) | 0.0524 (8) | |
O3 | 0.36480 (18) | 0.3066 (6) | 0.0488 (2) | 0.0602 (9) | |
O4 | 0.27254 (18) | 0.4666 (6) | 0.0561 (3) | 0.0595 (9) | |
N5 | 0.33454 (18) | 0.3938 (5) | 0.0985 (2) | 0.0354 (7) | |
H1A | −0.0373 | 0.7643 | 0.2290 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.0263 (4) | 0.0432 (4) | 0.0241 (4) | 0.000 | 0.0166 (3) | 0.000 |
O1 | 0.032 (2) | 0.044 (2) | 0.078 (3) | 0.000 | 0.019 (2) | 0.000 |
N1 | 0.0289 (15) | 0.0435 (17) | 0.0264 (15) | −0.0029 (13) | 0.0164 (12) | 0.0007 (13) |
N3 | 0.0378 (16) | 0.0423 (17) | 0.0264 (16) | −0.0011 (13) | 0.0188 (13) | −0.0035 (13) |
N2 | 0.0279 (15) | 0.0401 (17) | 0.0266 (16) | 0.0005 (12) | 0.0168 (13) | −0.0010 (12) |
N4 | 0.0322 (16) | 0.0508 (18) | 0.0331 (17) | 0.0035 (14) | 0.0217 (14) | −0.0002 (14) |
C3 | 0.0320 (18) | 0.0336 (18) | 0.0258 (17) | 0.0019 (14) | 0.0159 (15) | 0.0025 (14) |
C2 | 0.036 (2) | 0.052 (2) | 0.0254 (18) | −0.0093 (17) | 0.0096 (16) | −0.0052 (17) |
C1 | 0.0294 (18) | 0.049 (2) | 0.0324 (19) | −0.0077 (16) | 0.0134 (16) | 0.0002 (17) |
C4 | 0.0290 (17) | 0.0312 (16) | 0.0296 (18) | 0.0045 (14) | 0.0176 (15) | 0.0024 (14) |
C6 | 0.0290 (19) | 0.049 (2) | 0.033 (2) | −0.0021 (16) | 0.0127 (16) | −0.0040 (17) |
C5 | 0.0247 (18) | 0.057 (2) | 0.038 (2) | 0.0035 (16) | 0.0136 (16) | 0.0010 (18) |
O2 | 0.0557 (19) | 0.070 (2) | 0.0329 (16) | 0.0159 (16) | 0.0193 (14) | 0.0010 (14) |
O3 | 0.0444 (16) | 0.102 (3) | 0.0467 (17) | −0.0035 (18) | 0.0317 (15) | −0.0254 (18) |
O4 | 0.0412 (18) | 0.081 (2) | 0.0540 (19) | 0.0119 (17) | 0.0163 (15) | 0.0096 (18) |
N5 | 0.0333 (17) | 0.0433 (18) | 0.0345 (18) | −0.0007 (13) | 0.0187 (14) | 0.0040 (13) |
Geometric parameters (Å, º) top
Cu—N2i | 2.004 (3) | N4—C4 | 1.338 (5) |
Cu—N2 | 2.004 (3) | N4—C5 | 1.364 (5) |
Cu—N1 | 2.034 (3) | N4—H4 | 0.8600 |
Cu—N1i | 2.034 (3) | C3—C4 | 1.442 (5) |
Cu—O1 | 2.208 (4) | C2—C1 | 1.358 (5) |
O1—H1A | 0.8160 | C2—H2 | 0.9300 |
N1—C3 | 1.322 (5) | C1—H1 | 0.9300 |
N1—C1 | 1.374 (5) | C6—C5 | 1.349 (6) |
N3—C3 | 1.340 (5) | C6—H6 | 0.9300 |
N3—C2 | 1.371 (5) | C5—H5 | 0.9300 |
N3—H3 | 0.8600 | O2—N5 | 1.241 (4) |
N2—C4 | 1.323 (5) | O3—N5 | 1.243 (5) |
N2—C6 | 1.378 (5) | O4—N5 | 1.226 (4) |
| | | |
N2i—Cu—N2 | 178.28 (17) | C5—N4—H4 | 126.4 |
N2i—Cu—N1 | 97.47 (11) | N1—C3—N3 | 110.8 (3) |
N2—Cu—N1 | 82.09 (11) | N1—C3—C4 | 117.7 (3) |
N2i—Cu—N1i | 82.09 (11) | N3—C3—C4 | 131.4 (3) |
N2—Cu—N1i | 97.47 (11) | C1—C2—N3 | 106.8 (3) |
N1—Cu—N1i | 151.21 (18) | C1—C2—H2 | 126.6 |
N2i—Cu—O1 | 90.86 (8) | N3—C2—H2 | 126.6 |
N2—Cu—O1 | 90.86 (8) | C2—C1—N1 | 108.6 (3) |
N1—Cu—O1 | 104.40 (9) | C2—C1—H1 | 125.7 |
N1i—Cu—O1 | 104.40 (9) | N1—C1—H1 | 125.7 |
Cu—O1—H1A | 124.7 | N2—C4—N4 | 111.0 (3) |
C3—N1—C1 | 106.6 (3) | N2—C4—C3 | 116.7 (3) |
C3—N1—Cu | 111.0 (2) | N4—C4—C3 | 132.1 (3) |
C1—N1—Cu | 142.3 (3) | C5—C6—N2 | 108.8 (3) |
C3—N3—C2 | 107.3 (3) | C5—C6—H6 | 125.6 |
C3—N3—H3 | 126.3 | N2—C6—H6 | 125.6 |
C2—N3—H3 | 126.3 | C6—C5—N4 | 107.1 (3) |
C4—N2—C6 | 105.9 (3) | C6—C5—H5 | 126.5 |
C4—N2—Cu | 112.4 (2) | N4—C5—H5 | 126.5 |
C6—N2—Cu | 141.5 (3) | O4—N5—O2 | 120.4 (3) |
C4—N4—C5 | 107.2 (3) | O4—N5—O3 | 121.1 (4) |
C4—N4—H4 | 126.4 | O2—N5—O3 | 118.4 (3) |
| | | |
N2i—Cu—N1—C3 | −177.0 (3) | C2—N3—C3—C4 | −175.5 (4) |
N2—Cu—N1—C3 | 1.3 (2) | C3—N3—C2—C1 | −0.3 (4) |
N1i—Cu—N1—C3 | −89.8 (2) | N3—C2—C1—N1 | 0.6 (5) |
O1—Cu—N1—C3 | 90.2 (2) | C3—N1—C1—C2 | −0.7 (4) |
N2i—Cu—N1—C1 | 7.0 (5) | Cu—N1—C1—C2 | 175.4 (3) |
N2—Cu—N1—C1 | −174.7 (5) | C6—N2—C4—N4 | 0.7 (4) |
N1i—Cu—N1—C1 | 94.2 (4) | Cu—N2—C4—N4 | 177.3 (2) |
O1—Cu—N1—C1 | −85.8 (4) | C6—N2—C4—C3 | −174.9 (3) |
N1—Cu—N2—C4 | −1.6 (3) | Cu—N2—C4—C3 | 1.6 (4) |
N1i—Cu—N2—C4 | 149.3 (3) | C5—N4—C4—N2 | −0.8 (4) |
O1—Cu—N2—C4 | −106.0 (2) | C5—N4—C4—C3 | 173.9 (4) |
N1—Cu—N2—C6 | 173.0 (4) | N1—C3—C4—N2 | −0.5 (5) |
N1i—Cu—N2—C6 | −36.0 (4) | N3—C3—C4—N2 | 174.6 (4) |
O1—Cu—N2—C6 | 68.6 (4) | N1—C3—C4—N4 | −175.0 (4) |
C1—N1—C3—N3 | 0.5 (4) | N3—C3—C4—N4 | 0.1 (7) |
Cu—N1—C3—N3 | −176.9 (2) | C4—N2—C6—C5 | −0.3 (4) |
C1—N1—C3—C4 | 176.6 (3) | Cu—N2—C6—C5 | −175.2 (3) |
Cu—N1—C3—C4 | −0.9 (4) | N2—C6—C5—N4 | −0.2 (5) |
C2—N3—C3—N1 | −0.2 (4) | C4—N4—C5—C6 | 0.6 (4) |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3ii | 0.86 | 2.03 | 2.790 (4) | 147 |
N3—H3···O1iii | 0.86 | 2.64 | 3.237 (3) | 128 |
N4—H4···O3ii | 0.86 | 2.07 | 2.821 (5) | 146 |
N4—H4···O4 | 0.86 | 2.52 | 3.089 (5) | 125 |
O1—H1A···O2iv | 0.82 | 1.96 | 2.769 (4) | 171 |
O1—H1A···O3iv | 0.82 | 2.54 | 3.126 (4) | 130 |
O1—H1A···N5iv | 0.82 | 2.61 | 3.379 (4) | 157 |
Symmetry codes: (ii) −x+1/2, −y+1/2, −z; (iii) −x, −y+1, −z; (iv) x−1/2, y+1/2, z. |