In the title compound, [Co(C4H4O5)(C7H5N3O2)(H2O)2]·H2O, the CoII atom is coordinated by one tridentate oxydiacetate dianion, one monodentate nitrobenzimidazole molecule and two water molecules in a distorted octahedral geometry. The face-to-face distance of 3.345 (14) Å between parallel nitrobenzimidazole ligands of neighboring complexes indicates the existence of π–π stacking.
Supporting information
CCDC reference: 274409
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.110
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.62 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O9 - N4 .. 6.56 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co - O3 .. 6.87 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
3 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Diaqua(5-nitro-1
H-benzimidazole-
κN3)(oxydiacetato-
κO,
O',
O'')cobalt(II) monohydrate
top
Crystal data top
[Co(C4H4O5)(C7H5N3O2)(H2O)2]·H2O | F(000) = 836 |
Mr = 408.19 | Dx = 1.792 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10912 reflections |
a = 11.5641 (5) Å | θ = 2.4–25.0° |
b = 10.2592 (5) Å | µ = 1.20 mm−1 |
c = 12.7556 (6) Å | T = 295 K |
β = 90.3721 (12)° | Plate, red |
V = 1513.27 (12) Å3 | 0.31 × 0.20 × 0.08 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3468 independent reflections |
Radiation source: fine-focus sealed tube | 2938 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −13→13 |
Tmin = 0.740, Tmax = 0.902 | l = −16→14 |
14228 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)] = 0.042 | Hydrogen site location: difmap and geom |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.049P)2 + 1.5881P] where P = (Fo2 + 2Fc2)/3 |
3468 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.32 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 | |
Co | 0.81293 (3) | 0.70306 (3) | 0.40164 (3) | 0.02797 (12) | |
N1 | 0.6708 (2) | 1.0797 (2) | 0.3794 (2) | 0.0437 (6) | |
H1 | 0.6832 | 1.1624 | 0.3801 | 0.052* | |
N3 | 0.70764 (19) | 0.8668 (2) | 0.38228 (19) | 0.0335 (5) | |
N4 | 0.2903 (3) | 0.7654 (3) | 0.3546 (2) | 0.0545 (7) | |
O1 | 0.69458 (17) | 0.55624 (18) | 0.37906 (16) | 0.0366 (4) | |
O2 | 0.6649 (2) | 0.3439 (2) | 0.3898 (2) | 0.0527 (6) | |
O3 | 0.92366 (16) | 0.53079 (19) | 0.40151 (14) | 0.0348 (4) | |
O4 | 0.87361 (18) | 0.6990 (2) | 0.24664 (15) | 0.0408 (5) | |
O5 | 0.9943 (3) | 0.6020 (4) | 0.13776 (19) | 0.0914 (12) | |
O6 | 0.95654 (17) | 0.8135 (2) | 0.44664 (16) | 0.0410 (5) | |
H6A | 0.9575 | 0.8316 | 0.5150 | 0.050* | |
H6B | 1.0183 | 0.8128 | 0.4147 | 0.050* | |
O7 | 0.77940 (19) | 0.6799 (2) | 0.56376 (16) | 0.0441 (5) | |
H7A | 0.7056 | 0.6577 | 0.5755 | 0.050* | |
H7B | 0.8037 | 0.7205 | 0.6191 | 0.050* | |
O8 | 0.3062 (2) | 0.6474 (3) | 0.3529 (2) | 0.0685 (7) | |
O9 | 0.1923 (2) | 0.8140 (3) | 0.3502 (3) | 0.0856 (10) | |
O1W | 0.4351 (2) | 0.4110 (3) | 0.3934 (2) | 0.0692 (8) | |
H1A | 0.5105 | 0.3930 | 0.3855 | 0.050* | |
H1B | 0.4202 | 0.4957 | 0.3820 | 0.050* | |
C2 | 0.7503 (3) | 0.9860 (3) | 0.3847 (2) | 0.0408 (7) | |
H2 | 0.8291 | 1.0031 | 0.3897 | 0.049* | |
C4 | 0.4990 (2) | 0.7969 (3) | 0.3696 (2) | 0.0384 (6) | |
H4 | 0.5108 | 0.7072 | 0.3707 | 0.046* | |
C5 | 0.3883 (3) | 0.8529 (3) | 0.3625 (2) | 0.0403 (7) | |
C6 | 0.3684 (3) | 0.9866 (3) | 0.3604 (2) | 0.0483 (8) | |
H6 | 0.2928 | 1.0171 | 0.3555 | 0.058* | |
C7 | 0.4558 (3) | 1.0727 (3) | 0.3651 (2) | 0.0463 (7) | |
H7 | 0.4432 | 1.1622 | 0.3635 | 0.056* | |
C8 | 0.5664 (3) | 1.0198 (3) | 0.3727 (2) | 0.0378 (6) | |
C9 | 0.5888 (2) | 0.8851 (3) | 0.3747 (2) | 0.0331 (6) | |
C11 | 0.7280 (3) | 0.4419 (3) | 0.3930 (2) | 0.0358 (6) | |
C12 | 0.8546 (3) | 0.4187 (3) | 0.4184 (3) | 0.0466 (7) | |
H12A | 0.8620 | 0.3922 | 0.4911 | 0.056* | |
H12B | 0.8831 | 0.3480 | 0.3752 | 0.056* | |
C13 | 0.9942 (3) | 0.5275 (3) | 0.3105 (2) | 0.0451 (7) | |
H13A | 0.9972 | 0.4389 | 0.2841 | 0.054* | |
H13B | 1.0723 | 0.5532 | 0.3295 | 0.054* | |
C14 | 0.9498 (3) | 0.6167 (4) | 0.2245 (2) | 0.0454 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co | 0.02868 (19) | 0.02559 (19) | 0.02964 (19) | −0.00107 (14) | 0.00109 (13) | −0.00231 (14) |
N1 | 0.0553 (16) | 0.0254 (12) | 0.0503 (15) | 0.0000 (11) | 0.0060 (12) | 0.0027 (11) |
N3 | 0.0288 (11) | 0.0279 (11) | 0.0437 (13) | −0.0012 (9) | 0.0055 (10) | −0.0015 (10) |
N4 | 0.0448 (16) | 0.064 (2) | 0.0542 (17) | −0.0099 (14) | 0.0011 (13) | 0.0031 (15) |
O1 | 0.0388 (11) | 0.0246 (9) | 0.0462 (11) | −0.0010 (8) | −0.0070 (9) | −0.0026 (8) |
O2 | 0.0543 (14) | 0.0275 (10) | 0.0764 (17) | −0.0067 (10) | −0.0050 (12) | −0.0008 (11) |
O3 | 0.0380 (10) | 0.0354 (10) | 0.0311 (9) | 0.0019 (8) | −0.0028 (8) | 0.0013 (8) |
O4 | 0.0443 (11) | 0.0470 (12) | 0.0312 (10) | 0.0137 (10) | 0.0036 (8) | 0.0056 (9) |
O5 | 0.084 (2) | 0.156 (3) | 0.0348 (13) | 0.077 (2) | 0.0193 (12) | 0.0217 (16) |
O6 | 0.0341 (10) | 0.0511 (13) | 0.0379 (11) | −0.0119 (9) | 0.0041 (8) | −0.0062 (9) |
O7 | 0.0444 (11) | 0.0561 (13) | 0.0320 (10) | −0.0190 (10) | 0.0042 (9) | −0.0068 (9) |
O8 | 0.0594 (16) | 0.0578 (17) | 0.088 (2) | −0.0173 (13) | −0.0036 (14) | −0.0026 (15) |
O9 | 0.0319 (13) | 0.092 (2) | 0.132 (3) | 0.0051 (14) | −0.0017 (15) | 0.014 (2) |
O1W | 0.0481 (14) | 0.0512 (15) | 0.109 (2) | −0.0052 (12) | 0.0254 (14) | 0.0043 (15) |
C2 | 0.0404 (16) | 0.0305 (14) | 0.0518 (17) | −0.0049 (12) | 0.0087 (13) | −0.0001 (13) |
C4 | 0.0383 (15) | 0.0391 (15) | 0.0379 (15) | −0.0047 (13) | 0.0029 (12) | 0.0003 (13) |
C5 | 0.0359 (15) | 0.0514 (18) | 0.0335 (14) | −0.0081 (13) | −0.0006 (12) | 0.0005 (13) |
C6 | 0.0484 (18) | 0.055 (2) | 0.0412 (16) | 0.0143 (16) | −0.0003 (14) | 0.0005 (15) |
C7 | 0.0536 (19) | 0.0390 (16) | 0.0463 (17) | 0.0105 (14) | 0.0007 (14) | 0.0005 (14) |
C8 | 0.0467 (16) | 0.0356 (15) | 0.0313 (13) | 0.0078 (12) | 0.0034 (12) | 0.0016 (12) |
C9 | 0.0341 (13) | 0.0355 (14) | 0.0297 (13) | −0.0004 (11) | 0.0048 (10) | 0.0002 (11) |
C11 | 0.0462 (16) | 0.0283 (13) | 0.0328 (14) | −0.0022 (12) | −0.0003 (12) | −0.0024 (11) |
C12 | 0.0483 (17) | 0.0340 (15) | 0.0576 (19) | 0.0033 (13) | −0.0040 (15) | 0.0097 (14) |
C13 | 0.0377 (15) | 0.058 (2) | 0.0400 (16) | 0.0168 (14) | 0.0040 (12) | 0.0064 (14) |
C14 | 0.0350 (15) | 0.068 (2) | 0.0330 (14) | 0.0156 (15) | 0.0009 (12) | 0.0018 (15) |
Geometric parameters (Å, º) top
Co—O1 | 2.0541 (19) | O6—H6B | 0.8246 |
Co—O3 | 2.1824 (19) | O7—H7A | 0.8974 |
Co—O4 | 2.103 (2) | O7—H7B | 0.8646 |
Co—O6 | 2.0876 (19) | O1W—H1A | 0.8977 |
Co—O7 | 2.120 (2) | O1W—H1B | 0.8981 |
Co—N3 | 2.089 (2) | C2—H2 | 0.9300 |
N1—C2 | 1.331 (4) | C4—C9 | 1.378 (4) |
N1—C8 | 1.356 (4) | C4—C5 | 1.406 (4) |
N1—H1 | 0.8600 | C4—H4 | 0.9300 |
N3—C2 | 1.319 (4) | C5—C6 | 1.391 (5) |
N3—C9 | 1.390 (3) | C6—C7 | 1.343 (5) |
N4—O8 | 1.224 (4) | C6—H6 | 0.9300 |
N4—O9 | 1.239 (4) | C7—C8 | 1.392 (4) |
N4—C5 | 1.449 (4) | C7—H7 | 0.9300 |
O1—C11 | 1.248 (3) | C8—C9 | 1.407 (4) |
O2—C11 | 1.242 (3) | C11—C12 | 1.516 (4) |
O3—C12 | 1.417 (4) | C12—H12A | 0.9700 |
O3—C13 | 1.424 (3) | C12—H12B | 0.9700 |
O4—C14 | 1.254 (4) | C13—C14 | 1.516 (4) |
O5—C14 | 1.232 (4) | C13—H13A | 0.9700 |
O6—H6A | 0.8914 | C13—H13B | 0.9700 |
| | | |
O1—Co—O6 | 164.69 (8) | N1—C2—H2 | 122.9 |
O1—Co—N3 | 100.71 (8) | C9—C4—C5 | 114.8 (3) |
O6—Co—N3 | 93.34 (8) | C9—C4—H4 | 122.6 |
O1—Co—O4 | 94.58 (8) | C5—C4—H4 | 122.6 |
O6—Co—O4 | 89.97 (8) | C6—C5—C4 | 123.7 (3) |
N3—Co—O4 | 95.88 (8) | C6—C5—N4 | 118.7 (3) |
O1—Co—O7 | 85.91 (8) | C4—C5—N4 | 117.5 (3) |
O6—Co—O7 | 86.72 (8) | C7—C6—C5 | 121.5 (3) |
N3—Co—O7 | 95.46 (9) | C7—C6—H6 | 119.2 |
O4—Co—O7 | 168.35 (8) | C5—C6—H6 | 119.2 |
O1—Co—O3 | 78.26 (8) | C6—C7—C8 | 116.0 (3) |
O6—Co—O3 | 88.50 (8) | C6—C7—H7 | 122.0 |
N3—Co—O3 | 173.17 (8) | C8—C7—H7 | 122.0 |
O4—Co—O3 | 77.53 (7) | N1—C8—C7 | 130.1 (3) |
O7—Co—O3 | 91.21 (8) | N1—C8—C9 | 106.3 (3) |
C2—N1—C8 | 106.8 (2) | C7—C8—C9 | 123.6 (3) |
C2—N1—H1 | 126.6 | C4—C9—N3 | 131.2 (3) |
C8—N1—H1 | 126.6 | C4—C9—C8 | 120.4 (3) |
C2—N3—C9 | 104.2 (2) | N3—C9—C8 | 108.4 (2) |
C2—N3—Co | 121.71 (19) | O2—C11—O1 | 125.0 (3) |
C9—N3—Co | 133.79 (18) | O2—C11—C12 | 116.5 (3) |
O8—N4—O9 | 122.3 (3) | O1—C11—C12 | 118.4 (3) |
O8—N4—C5 | 119.8 (3) | O3—C12—C11 | 112.6 (2) |
O9—N4—C5 | 117.9 (3) | O3—C12—H12A | 109.1 |
C11—O1—Co | 117.63 (18) | C11—C12—H12A | 109.1 |
C12—O3—Co | 109.02 (16) | O3—C12—H12B | 109.1 |
C13—O3—Co | 111.03 (16) | C11—C12—H12B | 109.1 |
C14—O4—Co | 117.68 (19) | H12A—C12—H12B | 107.8 |
C12—O3—C13 | 115.5 (2) | O3—C13—C14 | 112.5 (2) |
Co—O6—H6A | 112.8 | O3—C13—H13A | 109.1 |
Co—O6—H6B | 123.3 | C14—C13—H13A | 109.1 |
H6A—O6—H6B | 118.7 | O3—C13—H13B | 109.1 |
Co—O7—H7A | 111.8 | C14—C13—H13B | 109.1 |
Co—O7—H7B | 133.0 | H13A—C13—H13B | 107.8 |
H7A—O7—H7B | 106.9 | O5—C14—O4 | 125.7 (3) |
H1A—O1W—H1B | 111.4 | O5—C14—C13 | 115.8 (3) |
N3—C2—N1 | 114.2 (3) | O4—C14—C13 | 118.6 (3) |
N3—C2—H2 | 122.9 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 1.88 | 2.715 (3) | 164 |
O1W—H1A···O2 | 0.90 | 1.86 | 2.746 (3) | 171 |
O1W—H1B···O8 | 0.90 | 2.07 | 2.891 (4) | 151 |
O6—H6A···O5ii | 0.89 | 1.76 | 2.621 (3) | 162 |
O6—H6B···O9iii | 0.82 | 2.18 | 2.998 (3) | 173 |
O7—H7A···O1Wiv | 0.90 | 1.82 | 2.709 (3) | 171 |
O7—H7B···O4ii | 0.86 | 1.99 | 2.853 (3) | 174 |
C2—H2···O6 | 0.93 | 2.54 | 3.069 (4) | 116 |
C2—H2···O5v | 0.93 | 2.31 | 3.199 (5) | 160 |
C7—H7···O1Wi | 0.93 | 2.58 | 3.498 (4) | 168 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z+1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (v) −x+2, y+1/2, −z+1/2. |