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In the title compound, [Cu(C7H5N3O2)2(H2O)2](NO3)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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804034300/cv6433sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804034300/cv6433Isup2.hkl
Contains datablock I

CCDC reference: 263529

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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-3H-benzimidazol) copper(II) dinitrate top
Crystal data top
[Cu(C7H5N3O2)2(H2O)2]2(NO3)Z = 1
Mr = 549.87F(000) = 279
Triclinic, P1Dx = 1.846 Mg m3
a = 7.2372 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1279 (9) ÅCell parameters from 2166 reflections
c = 9.1779 (10) Åθ = 2.4–27.5°
α = 69.491 (2)°µ = 1.19 mm1
β = 78.012 (2)°T = 293 K
γ = 84.999 (2)°Plate, blue
V = 494.57 (9) Å30.35 × 0.32 × 0.06 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2155 independent reflections
Radiation source: fine-focus sealed tube2051 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Detector resolution: 8.33 pixels mm-1θmax = 27.5°, θmin = 2.4°
ω scansh = 97
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.680, Tmax = 0.932l = 1111
3050 measured reflections
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H 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 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.26 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
Cu10.50000.00000.00000.02959 (12)
O1W0.3149 (2)0.1463 (2)0.12950 (18)0.0344 (3)
O10.2300 (3)0.4267 (2)0.84578 (19)0.0665 (6)
O20.3499 (3)0.5052 (2)0.6454 (2)0.0540 (4)
O30.6614 (2)0.2872 (2)0.12636 (19)0.0438 (4)
O40.9286 (2)0.39691 (19)0.2664 (2)0.0518 (4)
O50.9189 (2)0.1407 (2)0.0878 (2)0.0588 (5)
N10.2610 (2)0.2827 (2)0.28790 (19)0.0348 (4)
H10.22530.38370.29510.042*
N20.3813 (2)0.08288 (19)0.17878 (17)0.0316 (3)
N30.2836 (3)0.3933 (2)0.7032 (2)0.0392 (4)
N40.8365 (2)0.2760 (2)0.15957 (19)0.0339 (3)
C10.2495 (3)0.1261 (2)0.4104 (2)0.0289 (4)
C20.1797 (3)0.0858 (3)0.5721 (2)0.0341 (4)
H20.12810.17200.61440.041*
C30.1906 (3)0.0864 (3)0.6657 (2)0.0355 (4)
H30.14620.12000.77450.043*
C40.2686 (3)0.2118 (2)0.5973 (2)0.0312 (4)
C50.3374 (3)0.1763 (2)0.4369 (2)0.0294 (4)
H50.38720.26360.39550.035*
C60.3269 (2)0.0012 (2)0.3424 (2)0.0270 (3)
C70.3379 (3)0.2503 (2)0.1549 (2)0.0359 (4)
H70.35880.33710.05540.043*
H1W10.215 (4)0.127 (4)0.101 (3)0.046 (8)*
H2W10.333 (4)0.240 (4)0.179 (4)0.051 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0426 (2)0.02300 (17)0.01943 (16)0.00639 (12)0.00433 (12)0.00508 (12)
O1W0.0360 (8)0.0308 (7)0.0311 (7)0.0004 (6)0.0071 (6)0.0037 (6)
O10.1113 (17)0.0462 (10)0.0282 (8)0.0007 (10)0.0110 (9)0.0032 (7)
O20.0622 (10)0.0320 (8)0.0473 (9)0.0125 (7)0.0038 (8)0.0005 (7)
O30.0315 (7)0.0478 (8)0.0496 (9)0.0040 (6)0.0039 (6)0.0165 (7)
O40.0462 (9)0.0286 (7)0.0603 (10)0.0001 (6)0.0097 (8)0.0016 (7)
O50.0456 (9)0.0377 (8)0.0687 (12)0.0071 (7)0.0075 (8)0.0081 (8)
N10.0477 (9)0.0234 (7)0.0320 (8)0.0075 (6)0.0064 (7)0.0105 (6)
N20.0459 (9)0.0228 (7)0.0210 (7)0.0051 (6)0.0041 (6)0.0038 (6)
N30.0424 (9)0.0345 (9)0.0313 (8)0.0000 (7)0.0086 (7)0.0009 (7)
N40.0357 (8)0.0282 (7)0.0342 (8)0.0022 (6)0.0028 (7)0.0087 (7)
C10.0322 (9)0.0276 (8)0.0269 (8)0.0032 (7)0.0067 (7)0.0097 (7)
C20.0376 (10)0.0369 (10)0.0294 (9)0.0033 (8)0.0038 (7)0.0157 (8)
C30.0385 (10)0.0415 (10)0.0241 (8)0.0017 (8)0.0034 (7)0.0093 (8)
C40.0321 (9)0.0283 (9)0.0277 (9)0.0001 (7)0.0082 (7)0.0015 (7)
C50.0318 (9)0.0247 (8)0.0281 (8)0.0034 (7)0.0056 (7)0.0057 (7)
C60.0302 (8)0.0264 (8)0.0223 (8)0.0029 (6)0.0053 (6)0.0063 (7)
C70.0524 (12)0.0243 (8)0.0253 (9)0.0057 (8)0.0056 (8)0.0041 (7)
Geometric parameters (Å, º) top
Cu1—N21.9931 (15)N2—C71.320 (2)
Cu1—N2i1.9931 (15)N2—C61.400 (2)
Cu1—O1Wi2.0036 (14)N3—C41.464 (2)
Cu1—O1W2.0036 (14)C1—C21.394 (3)
O1W—H1W10.73 (3)C1—C61.407 (2)
O1W—H2W10.74 (3)C2—C31.368 (3)
O1—N31.223 (2)C2—H20.9300
O2—N31.223 (2)C3—C41.397 (3)
O3—N41.244 (2)C3—H30.9300
O4—N41.240 (2)C4—C51.387 (3)
O5—N41.241 (2)C5—C61.388 (2)
N1—C71.336 (2)C5—H50.9300
N1—C11.367 (2)C7—H70.9300
N1—H10.8600
N2—Cu1—N2i180.00 (11)N1—C1—C2131.06 (17)
N2—Cu1—O1Wi89.89 (6)N1—C1—C6105.90 (15)
N2i—Cu1—O1Wi90.11 (6)C2—C1—C6123.03 (17)
N2—Cu1—O1W90.11 (6)C3—C2—C1116.84 (17)
N2i—Cu1—O1W89.89 (6)C3—C2—H2121.6
O1Wi—Cu1—O1W180.00 (14)C1—C2—H2121.6
Cu1—O1W—H1W1118 (2)C2—C3—C4119.72 (17)
Cu1—O1W—H2W1122 (2)C2—C3—H3120.1
H1W1—O1W—H2W1113 (3)C4—C3—H3120.1
C7—N1—C1107.58 (15)C5—C4—C3124.84 (17)
C7—N1—H1126.2C5—C4—N3117.45 (17)
C1—N1—H1126.2C3—C4—N3117.68 (17)
C7—N2—C6104.89 (15)C4—C5—C6115.23 (16)
C7—N2—Cu1121.36 (12)C4—C5—H5122.4
C6—N2—Cu1133.74 (12)C6—C5—H5122.4
O2—N3—O1122.71 (18)C5—C6—N2131.43 (16)
O2—N3—C4118.64 (17)C5—C6—C1120.32 (16)
O1—N3—C4118.65 (18)N2—C6—C1108.25 (15)
O4—N4—O5119.91 (17)N2—C7—N1113.37 (16)
O4—N4—O3120.52 (16)N2—C7—H7123.3
O5—N4—O3119.55 (17)N1—C7—H7123.3
N2i—Cu1—N2—C7149 (100)O1—N3—C4—C31.0 (3)
O1Wi—Cu1—N2—C7134.74 (17)C3—C4—C5—C60.7 (3)
O1W—Cu1—N2—C745.26 (17)N3—C4—C5—C6177.52 (16)
N2i—Cu1—N2—C632 (100)C4—C5—C6—N2179.97 (19)
O1Wi—Cu1—N2—C644.79 (18)C4—C5—C6—C10.3 (3)
O1W—Cu1—N2—C6135.21 (18)C7—N2—C6—C5179.9 (2)
C7—N1—C1—C2179.3 (2)Cu1—N2—C6—C50.4 (3)
C7—N1—C1—C60.8 (2)C7—N2—C6—C10.3 (2)
N1—C1—C2—C3179.2 (2)Cu1—N2—C6—C1179.91 (14)
C6—C1—C2—C30.6 (3)N1—C1—C6—C5179.52 (17)
C1—C2—C3—C40.2 (3)C2—C1—C6—C50.3 (3)
C2—C3—C4—C50.5 (3)N1—C1—C6—N20.7 (2)
C2—C3—C4—N3177.78 (18)C2—C1—C6—N2179.44 (17)
O2—N3—C4—C52.3 (3)C6—N2—C7—N10.2 (2)
O1—N3—C4—C5177.4 (2)Cu1—N2—C7—N1179.44 (14)
O2—N3—C4—C3179.35 (19)C1—N1—C7—N20.7 (3)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4ii0.861.982.799 (2)158
O1W—H1W1···O5iii0.73 (3)2.12 (3)2.814 (2)161 (3)
O1W—H1W1···O5i0.73 (3)2.39 (3)2.882 (2)127 (3)
O1W—H2W1···O2iv0.74 (3)2.13 (3)2.857 (2)167 (3)
C7—H7···O1iv0.932.473.301 (2)149
C7—H7···O30.932.563.050 (2)114
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x, y+1, z1.
 

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