Buy article online - an online subscription or single-article purchase is required to access this article.
In the title compound, [Cu(C
7H
5N
3O
2)
2(H
2O)
2](NO
3)
2, the Cu atom, located on an inversion centre, is four-coordinated by the two O atoms from two water molecules and two N atoms from two benzimidazole ligands. The geometry around the Cu atom is nearly perfect square planar. The crystal packing is stabilized by intermolecular N—H
O, O—H
O and C—H
O hydrogen bonds.
Supporting information
CCDC reference: 263529
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.030
- wR factor = 0.083
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - O3 .. 19.29 su
PLAT430_ALERT_2_B Short Inter D...A Contact O5 .. O5 .. 2.63 Ang.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 2155
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2279
Completeness (_total/calc) 94.56%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
N2 -CU1 -N2 -C7 -149.00100.00 2.655 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4
N2 -CU1 -N2 -C6 32.00100.00 2.655 1.555 1.555 1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C14 H14 Cu1 N8 O12
Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Diaqua bis(6-nitro-3
H-benzimidazol) copper(II) dinitrate
top
Crystal data top
[Cu(C7H5N3O2)2(H2O)2]2(NO3) | Z = 1 |
Mr = 549.87 | F(000) = 279 |
Triclinic, P1 | Dx = 1.846 Mg m−3 |
a = 7.2372 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1279 (9) Å | Cell parameters from 2166 reflections |
c = 9.1779 (10) Å | θ = 2.4–27.5° |
α = 69.491 (2)° | µ = 1.19 mm−1 |
β = 78.012 (2)° | T = 293 K |
γ = 84.999 (2)° | Plate, blue |
V = 494.57 (9) Å3 | 0.35 × 0.32 × 0.06 mm |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 2155 independent reflections |
Radiation source: fine-focus sealed tube | 2051 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 2.4° |
ω scans | h = −9→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→10 |
Tmin = 0.680, Tmax = 0.932 | l = −11→11 |
3050 measured reflections | |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2519P] where P = (Fo2 + 2Fc2)/3 |
2155 reflections | (Δ/σ)max < 0.001 |
168 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | 0.5000 | 0.0000 | 0.0000 | 0.02959 (12) | |
O1W | 0.3149 (2) | 0.1463 (2) | −0.12950 (18) | 0.0344 (3) | |
O1 | 0.2300 (3) | −0.4267 (2) | 0.84578 (19) | 0.0665 (6) | |
O2 | 0.3499 (3) | −0.5052 (2) | 0.6454 (2) | 0.0540 (4) | |
O3 | 0.6614 (2) | 0.2872 (2) | −0.12636 (19) | 0.0438 (4) | |
O4 | 0.9286 (2) | 0.39691 (19) | −0.2664 (2) | 0.0518 (4) | |
O5 | 0.9189 (2) | 0.1407 (2) | −0.0878 (2) | 0.0588 (5) | |
N1 | 0.2610 (2) | 0.2827 (2) | 0.28790 (19) | 0.0348 (4) | |
H1 | 0.2253 | 0.3837 | 0.2951 | 0.042* | |
N2 | 0.3813 (2) | 0.08288 (19) | 0.17878 (17) | 0.0316 (3) | |
N3 | 0.2836 (3) | −0.3933 (2) | 0.7032 (2) | 0.0392 (4) | |
N4 | 0.8365 (2) | 0.2760 (2) | −0.15957 (19) | 0.0339 (3) | |
C1 | 0.2495 (3) | 0.1261 (2) | 0.4104 (2) | 0.0289 (4) | |
C2 | 0.1797 (3) | 0.0858 (3) | 0.5721 (2) | 0.0341 (4) | |
H2 | 0.1281 | 0.1720 | 0.6144 | 0.041* | |
C3 | 0.1906 (3) | −0.0864 (3) | 0.6657 (2) | 0.0355 (4) | |
H3 | 0.1462 | −0.1200 | 0.7745 | 0.043* | |
C4 | 0.2686 (3) | −0.2118 (2) | 0.5973 (2) | 0.0312 (4) | |
C5 | 0.3374 (3) | −0.1763 (2) | 0.4369 (2) | 0.0294 (4) | |
H5 | 0.3872 | −0.2636 | 0.3955 | 0.035* | |
C6 | 0.3269 (2) | −0.0012 (2) | 0.3424 (2) | 0.0270 (3) | |
C7 | 0.3379 (3) | 0.2503 (2) | 0.1549 (2) | 0.0359 (4) | |
H7 | 0.3588 | 0.3371 | 0.0554 | 0.043* | |
H1W1 | 0.215 (4) | 0.127 (4) | −0.101 (3) | 0.046 (8)* | |
H2W1 | 0.333 (4) | 0.240 (4) | −0.179 (4) | 0.051 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0426 (2) | 0.02300 (17) | 0.01943 (16) | 0.00639 (12) | −0.00433 (12) | −0.00508 (12) |
O1W | 0.0360 (8) | 0.0308 (7) | 0.0311 (7) | −0.0004 (6) | −0.0071 (6) | −0.0037 (6) |
O1 | 0.1113 (17) | 0.0462 (10) | 0.0282 (8) | −0.0007 (10) | −0.0110 (9) | 0.0032 (7) |
O2 | 0.0622 (10) | 0.0320 (8) | 0.0473 (9) | 0.0125 (7) | 0.0038 (8) | 0.0005 (7) |
O3 | 0.0315 (7) | 0.0478 (8) | 0.0496 (9) | 0.0040 (6) | −0.0039 (6) | −0.0165 (7) |
O4 | 0.0462 (9) | 0.0286 (7) | 0.0603 (10) | 0.0001 (6) | 0.0097 (8) | −0.0016 (7) |
O5 | 0.0456 (9) | 0.0377 (8) | 0.0687 (12) | 0.0071 (7) | −0.0075 (8) | 0.0081 (8) |
N1 | 0.0477 (9) | 0.0234 (7) | 0.0320 (8) | 0.0075 (6) | −0.0064 (7) | −0.0105 (6) |
N2 | 0.0459 (9) | 0.0228 (7) | 0.0210 (7) | 0.0051 (6) | −0.0041 (6) | −0.0038 (6) |
N3 | 0.0424 (9) | 0.0345 (9) | 0.0313 (8) | 0.0000 (7) | −0.0086 (7) | 0.0009 (7) |
N4 | 0.0357 (8) | 0.0282 (7) | 0.0342 (8) | 0.0022 (6) | −0.0028 (7) | −0.0087 (7) |
C1 | 0.0322 (9) | 0.0276 (8) | 0.0269 (8) | 0.0032 (7) | −0.0067 (7) | −0.0097 (7) |
C2 | 0.0376 (10) | 0.0369 (10) | 0.0294 (9) | 0.0033 (8) | −0.0038 (7) | −0.0157 (8) |
C3 | 0.0385 (10) | 0.0415 (10) | 0.0241 (8) | −0.0017 (8) | −0.0034 (7) | −0.0093 (8) |
C4 | 0.0321 (9) | 0.0283 (9) | 0.0277 (9) | −0.0001 (7) | −0.0082 (7) | −0.0015 (7) |
C5 | 0.0318 (9) | 0.0247 (8) | 0.0281 (8) | 0.0034 (7) | −0.0056 (7) | −0.0057 (7) |
C6 | 0.0302 (8) | 0.0264 (8) | 0.0223 (8) | 0.0029 (6) | −0.0053 (6) | −0.0063 (7) |
C7 | 0.0524 (12) | 0.0243 (8) | 0.0253 (9) | 0.0057 (8) | −0.0056 (8) | −0.0041 (7) |
Geometric parameters (Å, º) top
Cu1—N2 | 1.9931 (15) | N2—C7 | 1.320 (2) |
Cu1—N2i | 1.9931 (15) | N2—C6 | 1.400 (2) |
Cu1—O1Wi | 2.0036 (14) | N3—C4 | 1.464 (2) |
Cu1—O1W | 2.0036 (14) | C1—C2 | 1.394 (3) |
O1W—H1W1 | 0.73 (3) | C1—C6 | 1.407 (2) |
O1W—H2W1 | 0.74 (3) | C2—C3 | 1.368 (3) |
O1—N3 | 1.223 (2) | C2—H2 | 0.9300 |
O2—N3 | 1.223 (2) | C3—C4 | 1.397 (3) |
O3—N4 | 1.244 (2) | C3—H3 | 0.9300 |
O4—N4 | 1.240 (2) | C4—C5 | 1.387 (3) |
O5—N4 | 1.241 (2) | C5—C6 | 1.388 (2) |
N1—C7 | 1.336 (2) | C5—H5 | 0.9300 |
N1—C1 | 1.367 (2) | C7—H7 | 0.9300 |
N1—H1 | 0.8600 | | |
| | | |
N2—Cu1—N2i | 180.00 (11) | N1—C1—C2 | 131.06 (17) |
N2—Cu1—O1Wi | 89.89 (6) | N1—C1—C6 | 105.90 (15) |
N2i—Cu1—O1Wi | 90.11 (6) | C2—C1—C6 | 123.03 (17) |
N2—Cu1—O1W | 90.11 (6) | C3—C2—C1 | 116.84 (17) |
N2i—Cu1—O1W | 89.89 (6) | C3—C2—H2 | 121.6 |
O1Wi—Cu1—O1W | 180.00 (14) | C1—C2—H2 | 121.6 |
Cu1—O1W—H1W1 | 118 (2) | C2—C3—C4 | 119.72 (17) |
Cu1—O1W—H2W1 | 122 (2) | C2—C3—H3 | 120.1 |
H1W1—O1W—H2W1 | 113 (3) | C4—C3—H3 | 120.1 |
C7—N1—C1 | 107.58 (15) | C5—C4—C3 | 124.84 (17) |
C7—N1—H1 | 126.2 | C5—C4—N3 | 117.45 (17) |
C1—N1—H1 | 126.2 | C3—C4—N3 | 117.68 (17) |
C7—N2—C6 | 104.89 (15) | C4—C5—C6 | 115.23 (16) |
C7—N2—Cu1 | 121.36 (12) | C4—C5—H5 | 122.4 |
C6—N2—Cu1 | 133.74 (12) | C6—C5—H5 | 122.4 |
O2—N3—O1 | 122.71 (18) | C5—C6—N2 | 131.43 (16) |
O2—N3—C4 | 118.64 (17) | C5—C6—C1 | 120.32 (16) |
O1—N3—C4 | 118.65 (18) | N2—C6—C1 | 108.25 (15) |
O4—N4—O5 | 119.91 (17) | N2—C7—N1 | 113.37 (16) |
O4—N4—O3 | 120.52 (16) | N2—C7—H7 | 123.3 |
O5—N4—O3 | 119.55 (17) | N1—C7—H7 | 123.3 |
| | | |
N2i—Cu1—N2—C7 | −149 (100) | O1—N3—C4—C3 | −1.0 (3) |
O1Wi—Cu1—N2—C7 | 134.74 (17) | C3—C4—C5—C6 | 0.7 (3) |
O1W—Cu1—N2—C7 | −45.26 (17) | N3—C4—C5—C6 | −177.52 (16) |
N2i—Cu1—N2—C6 | 32 (100) | C4—C5—C6—N2 | 179.97 (19) |
O1Wi—Cu1—N2—C6 | −44.79 (18) | C4—C5—C6—C1 | −0.3 (3) |
O1W—Cu1—N2—C6 | 135.21 (18) | C7—N2—C6—C5 | −179.9 (2) |
C7—N1—C1—C2 | −179.3 (2) | Cu1—N2—C6—C5 | −0.4 (3) |
C7—N1—C1—C6 | 0.8 (2) | C7—N2—C6—C1 | 0.3 (2) |
N1—C1—C2—C3 | −179.2 (2) | Cu1—N2—C6—C1 | 179.91 (14) |
C6—C1—C2—C3 | 0.6 (3) | N1—C1—C6—C5 | 179.52 (17) |
C1—C2—C3—C4 | −0.2 (3) | C2—C1—C6—C5 | −0.3 (3) |
C2—C3—C4—C5 | −0.5 (3) | N1—C1—C6—N2 | −0.7 (2) |
C2—C3—C4—N3 | 177.78 (18) | C2—C1—C6—N2 | 179.44 (17) |
O2—N3—C4—C5 | −2.3 (3) | C6—N2—C7—N1 | 0.2 (2) |
O1—N3—C4—C5 | 177.4 (2) | Cu1—N2—C7—N1 | −179.44 (14) |
O2—N3—C4—C3 | 179.35 (19) | C1—N1—C7—N2 | −0.7 (3) |
Symmetry code: (i) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4ii | 0.86 | 1.98 | 2.799 (2) | 158 |
O1W—H1W1···O5iii | 0.73 (3) | 2.12 (3) | 2.814 (2) | 161 (3) |
O1W—H1W1···O5i | 0.73 (3) | 2.39 (3) | 2.882 (2) | 127 (3) |
O1W—H2W1···O2iv | 0.74 (3) | 2.13 (3) | 2.857 (2) | 167 (3) |
C7—H7···O1iv | 0.93 | 2.47 | 3.301 (2) | 149 |
C7—H7···O3 | 0.93 | 2.56 | 3.050 (2) | 114 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) x, y+1, z−1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.