Tetra­aqua­bis(1,3-benzimidazol-3-ium-1,3-diacetato)cobalt(II) hemihydrate

In the centrosymmetric title compound, [Co(C₁₁H₉N₂O₄)₂(H₂O)₄]·0.5H₂O, the Co^II complex has a distorted octa­hedral coordination geometry with two monodentate ligands and four water mol­ecules. The crystal packing is stabilized by inter­molecular O—H...O and C—H...O hydrogen bonds and a π–π stacking inter­action.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.045
• wR factor = 0.103
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.

   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

   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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Tetraaquabis(1,3-benzimidazol-3-ium-1,3-diacetato)cobalt(II) hemihydrate

Crystal data

[Co(C11H9N2O4)2(H2O)4]·0.5H2O	Z = 1
Mr = 606.41	F(000) = 314
Triclinic, P1	Dx = 1.582 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4237 (9) Å	Cell parameters from 205 reflections
b = 9.4197 (11) Å	θ = 2.2–25.1°
c = 9.6478 (11) Å	µ = 0.75 mm^−1
α = 81.432 (2)°	T = 273 K
β = 75.952 (2)°	Block, red
γ = 77.838 (2)°	0.22 × 0.14 × 0.10 mm
V = 636.38 (13) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	2224 independent reflections
Radiation source: fine-focus sealed tube	2019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω and φ scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→7
Tmin = 0.853, Tmax = 0.929	k = −11→7
3375 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.3708P] where P = (Fo^2 + 2Fc^2)/3
2224 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.37 e Å^−3
3 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	1.0000	0.0000	0.5000	0.02728 (19)
O1	0.9352 (3)	0.0984 (2)	0.3074 (2)	0.0383 (5)
O2	0.9013 (4)	−0.0800 (2)	0.1923 (2)	0.0506 (6)
O3	0.4137 (3)	0.6480 (3)	0.3755 (3)	0.0516 (6)
O4	0.5434 (3)	0.7848 (2)	0.4780 (2)	0.0434 (6)
O5	0.9401 (3)	0.2046 (2)	0.5792 (2)	0.0361 (5)
H5A	0.9808	0.1828	0.6561	0.054*
H5B	0.8274	0.2514	0.5897	0.054*
O6	0.7169 (3)	−0.0306 (2)	0.5723 (2)	0.0383 (5)
H6A	0.6932	−0.1028	0.5412	0.057*
H6B	0.6486	0.0512	0.5537	0.057*
O7	0.6169 (15)	0.0615 (11)	0.8695 (9)	0.056 (3)	0.25
H7A	0.7154	0.0087	0.8254	0.084*	0.25
H7B	0.5096	0.0511	0.8615	0.084*	0.25
N1	0.7378 (3)	0.3103 (2)	0.1477 (2)	0.0311 (6)
N2	0.7496 (3)	0.5086 (2)	0.2345 (2)	0.0299 (5)
C9	0.8725 (4)	0.0484 (3)	0.2190 (3)	0.0326 (7)
C8	0.7411 (5)	0.1559 (3)	0.1372 (4)	0.0414 (8)
H8A	0.7788	0.1387	0.0367	0.050*
H8B	0.6140	0.1362	0.1730	0.050*
C1	0.7382 (4)	0.3684 (3)	0.2650 (3)	0.0322 (7)
H1	0.7315	0.3176	0.3560	0.039*
C7	0.7537 (4)	0.5463 (3)	0.0888 (3)	0.0293 (6)
C6	0.7456 (4)	0.4209 (3)	0.0337 (3)	0.0286 (6)
C5	0.7423 (4)	0.4207 (3)	−0.1096 (3)	0.0375 (7)
H5	0.7338	0.3372	−0.1466	0.045*
C4	0.7521 (5)	0.5510 (4)	−0.1933 (3)	0.0468 (8)
H4	0.7501	0.5558	−0.2899	0.056*
C3	0.7651 (5)	0.6767 (4)	−0.1391 (4)	0.0479 (9)
H3	0.7738	0.7620	−0.2008	0.057*
C2	0.7656 (4)	0.6784 (3)	0.0031 (4)	0.0416 (8)
H2	0.7733	0.7623	0.0398	0.050*
C10	0.7468 (4)	0.6069 (3)	0.3378 (3)	0.0365 (7)
H10A	0.8254	0.6782	0.2913	0.044*
H10B	0.8016	0.5513	0.4154	0.044*
C11	0.5504 (4)	0.6869 (3)	0.4008 (3)	0.0317 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0288 (3)	0.0226 (3)	0.0330 (3)	−0.0009 (2)	−0.0116 (2)	−0.0084 (2)
O1	0.0508 (13)	0.0281 (11)	0.0426 (12)	−0.0062 (9)	−0.0241 (10)	−0.0028 (9)
O2	0.0771 (18)	0.0259 (12)	0.0561 (15)	−0.0017 (11)	−0.0318 (13)	−0.0096 (10)
O3	0.0343 (12)	0.0585 (15)	0.0698 (16)	0.0042 (11)	−0.0197 (11)	−0.0356 (13)
O4	0.0402 (12)	0.0363 (13)	0.0574 (14)	−0.0010 (10)	−0.0087 (11)	−0.0277 (11)
O5	0.0361 (11)	0.0310 (11)	0.0444 (12)	0.0022 (9)	−0.0160 (9)	−0.0136 (9)
O6	0.0325 (11)	0.0313 (11)	0.0535 (13)	−0.0038 (9)	−0.0113 (10)	−0.0121 (10)
O7	0.084 (8)	0.056 (6)	0.031 (5)	−0.021 (5)	0.000 (5)	−0.021 (4)
N1	0.0423 (14)	0.0228 (12)	0.0304 (13)	−0.0025 (10)	−0.0125 (11)	−0.0067 (10)
N2	0.0316 (13)	0.0275 (13)	0.0321 (13)	0.0004 (10)	−0.0086 (10)	−0.0140 (10)
C9	0.0393 (17)	0.0279 (16)	0.0322 (16)	−0.0071 (13)	−0.0094 (13)	−0.0040 (12)
C8	0.057 (2)	0.0261 (16)	0.0493 (19)	−0.0053 (14)	−0.0264 (16)	−0.0084 (14)
C1	0.0373 (16)	0.0295 (16)	0.0291 (15)	−0.0007 (13)	−0.0091 (13)	−0.0057 (12)
C7	0.0230 (14)	0.0317 (16)	0.0320 (15)	0.0000 (12)	−0.0057 (11)	−0.0068 (12)
C6	0.0252 (14)	0.0292 (15)	0.0311 (15)	0.0008 (12)	−0.0080 (12)	−0.0073 (12)
C5	0.0378 (17)	0.0423 (18)	0.0331 (16)	−0.0003 (14)	−0.0113 (13)	−0.0100 (14)
C4	0.046 (2)	0.061 (2)	0.0317 (17)	−0.0072 (17)	−0.0105 (15)	0.0010 (16)
C3	0.045 (2)	0.048 (2)	0.046 (2)	−0.0133 (16)	−0.0099 (16)	0.0148 (16)
C2	0.0384 (18)	0.0327 (18)	0.053 (2)	−0.0079 (14)	−0.0090 (15)	−0.0007 (15)
C10	0.0345 (16)	0.0344 (17)	0.0448 (18)	−0.0002 (13)	−0.0120 (14)	−0.0204 (14)
C11	0.0347 (16)	0.0277 (16)	0.0327 (16)	0.0010 (12)	−0.0088 (13)	−0.0104 (13)

Geometric parameters (Å, º)

Co1—O1	2.0677 (19)	N2—C7	1.392 (4)
Co1—O1^i	2.0677 (19)	N2—C10	1.452 (3)
Co1—O5^i	2.0995 (19)	C1—H1	0.9300
Co1—O5	2.0995 (19)	C2—C3	1.375 (5)
Co1—O6	2.114 (2)	C2—C7	1.394 (4)
Co1—O6^i	2.114 (2)	C2—H2	0.9300
O1—C9	1.253 (3)	C3—C4	1.394 (5)
O2—C9	1.238 (3)	C3—H3	0.9300
O3—C11	1.236 (4)	C4—C5	1.371 (4)
O4—C11	1.254 (3)	C4—H4	0.9300
O5—H5A	0.85	C5—C6	1.389 (4)
O5—H5B	0.85	C5—H5	0.9300
O6—H6A	0.85	C6—C7	1.384 (4)
O6—H6B	0.85	C8—C9	1.523 (4)
O7—H7A	0.85	C8—H8A	0.9700
O7—H7B	0.85	C8—H8B	0.9700
N1—C1	1.330 (4)	C10—C11	1.519 (4)
N1—C6	1.397 (4)	C10—H10A	0.9700
N1—C8	1.468 (3)	C10—H10B	0.9700
N2—C1	1.325 (4)
O1^i—Co1—O1	180.0	C9—C8—H8A	108.6
O1^i—Co1—O5^i	90.24 (8)	N1—C8—H8B	108.6
O1—Co1—O5^i	89.76 (8)	C9—C8—H8B	108.6
O1^i—Co1—O5	89.76 (8)	H8A—C8—H8B	107.5
O1—Co1—O5	90.24 (8)	N2—C1—N1	110.6 (3)
O5^i—Co1—O5	180.0	N2—C1—H1	124.7
O1^i—Co1—O6	91.42 (8)	N1—C1—H1	124.7
O1—Co1—O6	88.58 (8)	C6—C7—N2	106.6 (2)
O5^i—Co1—O6	87.27 (8)	C6—C7—C2	122.1 (3)
O5—Co1—O6	92.73 (8)	N2—C7—C2	131.3 (3)
O1^i—Co1—O6^i	88.58 (8)	C7—C6—C5	121.8 (3)
O1—Co1—O6^i	91.42 (8)	C7—C6—N1	106.8 (2)
O5^i—Co1—O6^i	92.73 (8)	C5—C6—N1	131.4 (3)
O5—Co1—O6^i	87.27 (8)	C4—C5—C6	115.9 (3)
O6—Co1—O6^i	180.0	C4—C5—H5	122.0
C9—O1—Co1	129.60 (19)	C6—C5—H5	122.0
Co1—O5—H5A	101.1	C5—C4—C3	122.5 (3)
Co1—O5—H5B	117.8	C5—C4—H4	118.8
H5A—O5—H5B	114.7	C3—C4—H4	118.8
Co1—O6—H6A	114.1	C2—C3—C4	121.9 (3)
Co1—O6—H6B	106.2	C2—C3—H3	119.0
H6A—O6—H6B	115.4	C4—C3—H3	119.0
H7A—O7—H7B	119.4	C3—C2—C7	115.7 (3)
C1—N1—C6	107.8 (2)	C3—C2—H2	122.1
C1—N1—C8	126.3 (2)	C7—C2—H2	122.1
C6—N1—C8	125.9 (2)	N2—C10—C11	113.7 (2)
C1—N2—C7	108.3 (2)	N2—C10—H10A	108.8
C1—N2—C10	125.4 (3)	C11—C10—H10A	108.8
C7—N2—C10	126.2 (2)	N2—C10—H10B	108.8
O2—C9—O1	127.4 (3)	C11—C10—H10B	108.8
O2—C9—C8	115.5 (3)	H10A—C10—H10B	107.7
O1—C9—C8	117.0 (3)	O3—C11—O4	126.2 (3)
N1—C8—C9	114.8 (2)	O3—C11—C10	118.0 (3)
N1—C8—H8A	108.6	O4—C11—C10	115.8 (3)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2^i	0.85	1.92	2.744 (3)	163
O5—H5B···O3^ii	0.85	1.82	2.666 (3)	176
O6—H6A···O4^iii	0.85	1.94	2.738 (3)	157
O6—H6B···O4^ii	0.85	1.91	2.750 (3)	169
O7—H7A···O6	0.85	2.52	2.993 (9)	116
C1—H1···O1	0.93	2.32	2.681 (3)	102
C1—H1···O3^ii	0.93	2.59	3.367 (4)	141
C1—H1···O4^ii	0.93	2.54	3.208 (4)	129
C10—H10A···O2^iv	0.97	2.46	3.375 (4)	157

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) x, y+1, z.